Fund/Build/Scale

Rob Biederman has sat on both sides of the table — first as co-founder and CEO of Catalant Technologies, and now as managing partner at Asymmetric Capital Partners. In this candid conversation, he explains why so much of the conventional wisdom around startups is actually counterproductive. He breaks down why design partners don't equal traction, why headcount growth is a vanity metric, and why Silicon Valley should stop romanticizing failure. He also shares how Asymmetric evaluates founders, what investors really care about, and the simple test every startup should use to prove they're solving a real problem. If you're a founder chasing milestones that look good on a pitch deck but don't move the business forward, this episode of Fund/Build/Scale is a reality check you won't hear anywhere else.   RUNTIME 43:43   EPISODE BREAKDOWN (2:46) “ We have a probably a couple points of differentiation with the broader market.” (4:46) “ Our happiest spot is kind of in the two-to-six million range for our first check.” (5:39) “ We want to get to know people probably a year or two before they're going to found so we can really see what they're about and really understand.” (7:20) “ I think we'd hire most of our founders as investors at our firm, if we had the chance.” (10:11) What makes a startup  relevant, credible, or just differentiated? (11:32) An easy framework for self-auditing your startup idea. (13:09) “ I think our industry kind of worships at the altar of failure a little too much.” (15:08) “ We don't actually really love backing people directly from really big companies.” (17:00) Rob explains why design partners are a distraction, not a path to real traction. (21:23) “ If you're gonna get one career, why not spend it trying to trick the world into doing something differently?” (24:17) One metric founders love that does not predict success from an investor's perspective. (25:08) Inside Asymmetric Capital Partners' four-step pitch review process. (27:27) Why the best data rooms are simple: “they have no spin.” (29:46) Rob describes how his firm's advisor partner model works. (31:49) The first step in GTM: “ get to the bottom of why your customer is buying from you.” (35:18) At the start, tell investors “everything you haven't figured out” so you can start planning. (38:17) “ If you don't tell your doctor the truth, what can they do for you?” (41:02) What he would do differently if he were launching a startup today. LINKS Rob Biederman Asymmetric Capital Partners Asymmetric FAQs Catalant Technologies Democratizing Care: Announcing our Investment in Counsel Health EvolutionIQ Raises $21M Series A To Deliver AI Based Claims Guidance Across The Industry SUBSCRIBE

Pro tip: If you can't see yourself getting up every morning for the next ten years and being excited about going to work, don't launch a startup. Ajay Prakash co-founded Rinse in 2013 to take the friction out of laundry and dry cleaning — for consumers, and for the small, family-owned businesses behind the counter. Since then, Rinse has scaled into a national brand, and Ajay has become a lecturer at Stanford Graduate Business School's Startup Garage, where he teaches frameworks for validating ideas, testing business models, and knowing when it's time to take the leap into entrepreneurship. I invited him on to share what he's learned about developing domain expertise from scratch, building trust with co-founders, and avoiding the early mistakes that can derail a promising business. RUNTIME 42:38 EPISODE BREAKDOWN (2:22) Ajay talks about two trends that led him to co-found Rinse in 2013. (4:15) Rinse co-founder James Joun was “one of my best friends from college.” (5:29) “When we started, we spent a lot of time with James' parents in the dry-cleaning store.” (6:40) Before taking the leap, founders should identify their “passion, expertise, and market opportunity.” (9:11) “As you build a company, answering the question of ‘why now' and ‘why me' is really important.” (11:19) “We signed up 11 of our friends. We picked up their clothes.” (14:17) “Every smart investor we talked to… told us we had to be on-demand.” (17:41) Early signals led Rinse to pivot from pricing per pound to adopting a subscription model. (20:23) His approach to crafting customer personas. (22:05) “We always envisioned helping the local cleaners.” (27:11) From the start, Rinse used Net Promoter Scores and surveys to glean customer insights. (30:44) The “two general areas of lessons” Ajay teaches at Stanford's Startup Garage. (34:53) Why he encourages Startup Garage students to keep asking themselves, “Am I still excited?” (37:41) How to prepare for the mental challenges of being a startup founder. (40:01) Is Rinse's operational model adaptable to other industries and services? LINKS Ajay Prakash James Joun Rinse The Four Steps to the Epiphany, Steven G. Blank The Lean Startup, Eric Ries Startup Garage at Stanford Graduate School of Business SUBSCRIBE

Karthee Madasamy is the founder of VC firm MFV Partners and the founding managing partner of Harper Court Ventures, both of which focus on early-stage deep tech startups. In this episode of Fund/Build/Scale, he explains what early-stage founders get wrong about TAM, why technical validation isn't enough, and how to de-risk your company when the market barely exists. We also talk about: What MFV looks for when evaluating scientific founders The importance of “market inevitability” and strategic timing Common missteps deep tech founders make on the road to Series A If you're building ambitious technology in a complex, slow-moving market, this episode will help you speak investors' language — and build a company they can believe in.   RUNTIME 41:03   EPISODE BREAKDOWN (2:24) Karthee describes his engineer–product manager–VC career path. (4:37) How does MFV Partners define deep tech? (6:35) Areas of interest include robotics, physical AI, and next-gen computing—“especially quantum.” (8:39) “We are doing anywhere from pre-seed to seed, up to all the way to Series A.” (12:17) About a third of the founders he works with are transitioning from academic or research roles. (14:01) Inside MFV's due diligence process. (16:20) The three questions Karthee uses to frame his first meeting with a founder. (17:47) Tactics for engineers and academics who want to validate their idea but lack customer experience. (19:27) “There's no fallback. You have to basically go deep on one thing.” (23:43) “A deep tech founder, in addition to all the other risks, they're taking technical risks.” (25:51) What does traction look like at an early-stage deep tech startup? (28:38) Be prepared to answer this question during your first meeting with Karthee. (30:32) “In deep tech, oftentimes, there is not a place you can just go to get a TAM.” (37:40) Why MFV accepts cold pitches. (39:24) The one question Karthee would ask the CEO if he were interviewing for a job at an early-stage startup. LINKS Karthee Madasamy MFV Partners Harper Court Ventures SUBSCRIBE

Jyoti Bansal sold his first company, AppDynamics, to Cisco for $3.7 billion. Harness, his next company, reached a similar valuation a few years later. As an entrepreneur — and as a VC at Unusual Ventures — Jyoti has built and backed multiple billion-dollar startups. But despite his track record, he says technical founders often overlook the same hard truth: good ideas don't build great companies. It's all about execution. In this conversation, Jyoti explains how he helps engineers become CEOs, the leadership frameworks he uses to scale fast without breaking culture, and why each business unit inside Harness runs like a startup of its own. He also talks about what he had to unlearn as he made the leap from founder to investor, and debunks the myth that every entrepreneur needs a mentor. If you're aiming for breakout scale, this episode will give you some useful tactics — and maybe a few reality checks. RUNTIME 44:24 EPISODE BREAKDOWN (3:23) “ I started Big Labs and I call it a startup studio: it's really my lab, a research lab for me to experiment with ideas and projects that I'm excited about.” (6:15) Why Jyoti still carves out time for customer discovery and sales calls. (7:27) “ Harness is designed for kind of this next-generation, AI-based approach for DevOps.” (9:42) “ Our entire philosophy is built with this concept called ‘startups within a startup.'” (11:22) How Harness maintains cohesion and alignment across 16 different modules. (14:00) The specific traits and abilities Jyoti looks for when hiring leaders at Harness. (17:35) Why some engineers are poorly suited to make the leap into entrepreneurship. (20:55) A mental framework that helped Jyoti become a better manager and communicator. (23:59) “ I always leaned on topic-based mentorship, not generic mentorship, which is a particular problem.” (25:53) Why working with a CEO coach “didn't work very well for me.” (27:36) The sectors and types of startups that interest him the most right now. (30:10) How he prefers to be pitched — and how to apply to Unusual Academy's next cohort. (32:24) “ 30, 40% growth rates are where most startups should be looking, at least — ideally much more.” (33:53) “ If we can't see a path to $100M of revenue — or a billion of revenue — we don't invest.” (37:15) The biggest attachment he had to let go of when transitioning from founder to VC. (42:41) The one question he'd ask the CEO if he were interviewing for a job with an early-stage startup. LINKS Jyoti Bansal Harness Traceable Unusual Ventures Unusual Academy Unusual Field Guide Cisco Announces Intent to Acquire Application Performance Monitoring Leader AppDynamics, 1/24/2017 SUBSCRIBE

Brian Rothenberg, partner at Defy and former VP of Growth at Eventbrite, joins Fund/Build/Scale to share what really matters when evaluating early-stage startups. From spotting false signals of traction to building defensible business models, Brian offers practical advice for both founders and operators. He also explains why job seekers should “think like a VC” before joining a startup, how he prefers to be pitched, and what signals he looks for in AI and emerging tech companies. Whether you're raising capital, building a company, or considering your next role, this conversation will help you see the startup landscape through an investor's eyes. RUNTIME 34:28   EPISODE BREAKDOWN (2:14) “ I've been fortunate to always be pretty entrepreneurial… it was just how I was wired.” (5:11) How advising friends and investing in their companies led Brian into VC. (6:45) “ The bulk of our capital goes to seed, seed plus or Series A. But we do go as early as an idea and a person.” (7:48) Defy's areas of interest and average check size. (8:53) “ We will be entering into a period where we'll see a lot of new and profoundly different consumer AI experiences.” (10:26) “ I see a lot of promise in rewiring a lot of the financial infrastructure and plumbing through use of blockchain.” (12:42) The traits and metrics Defy looks for in early-stage AI startups. (14:33) Brian loves Sean Ellis' customer satisfaction survey. (15:55)  Why proof-of-concept programs don't generate recurring revenue or reduce churn rates. (19:01) Have you noticed that we don't hear about many AI startups making a pivot? (21:00) Thanks to AI tools, “ we will see a lot more niche businesses and founders not having to dilute themselves as much as they had previously.” (22:22) How Brian grades the VC community's ability to judge AI traction. (24:42) Technology alone doesn't build a defensible startup. (26:57) How to pitch the team at Defy. (29:40) Why startup job seekers need to start thinking like investors. (32:58) The one question Brian would ask the CEO if he were interviewing for a job with an early-stage startup. LINKS Brian Rothenberg Defy Growth with Sean Ellis SUBSCRIBE

When you're raising your first rounds, every cap table decision can echo for years. Give away too much equity early, lock yourself into restrictive pro rata rights, or over-optimize for valuation — and you may find yourself boxed in just when your company starts to grow. Pulley co-founder and CEO Yin Wu has seen these mistakes firsthand. In this episode of Fund/Build/Scale, she offers practical, founder-first strategies for structuring and managing your cap table so you can attract top talent, keep your options open, and stay in control of your startup's destiny. We also discuss how to compete with entrenched incumbents, why her LinkedIn profile says she works in Customer Success, and how founders can shift their role as the company scales. RUNTIME 38:44 EPISODE BREAKDOWN (2:46) Why her LinkedIn profile says she's in “customer success,” not CEO/co-founder. (5:43)  How much time passed between Day Zero and serving Pulley's first customer? (9:48) “ You're trying to market the product, and then you're also playing the role of customer success at the same time.” (10:04) The number-one cap table mistake founders make? “Being too greedy.” (13:55) Why are startups sticking with four-year vesting schedules when it takes 7-10 years to exit? (15:14) How founders should think about pro rata rights in early rounds. (19:04) Taking money out in a secondary “ actually releases some of the pressure and allows founders to focus.” (21:04) Founder-preferred shares “are becoming increasingly popular.” (24:15) CEO/founders need to remember “ the soft power that you have as a leader of the company.” (26:45) How Yin defines “founder mode.” (30:50) “ Every successful company has been a response to some incumbent's worldview.” (33:38) Why going public “ can actually make it tough for companies to be able to innovate.” (34:04) The one question she'd ask the CEO if she were interviewing for a job with an early-stage startup. LINKS Yin Wu Pulley How to Scale a Startup in Just 3 Months, Pulley Employee Equity, Sam Altman Will the Blockbuster Deal for Wiz Spur an M&A Wave in Cybersecurity?, WSJ Pro VC SUBSCRIBE

A turbulent flight sparked Wayne Slavin's idea for Sure: let consumers buy insurance in real time. But after launching as a D2C app, he realized the bigger opportunity was powering insurance sales for others. Sure's pivot to B2B turned it into a vertical SaaS platform that lets enterprise companies embed insurance at the point of transaction. In this episode, Wayne explains how to pivot without losing your mission, why founders should lead early enterprise sales, and why he refuses to run proof-of-concept deals. He also shares why — if he could do it over — he'd avoid launching a business with so much built-in complexity. RUNTIME 51:58 EPISODE BREAKDOWN (3:16) How a turbulent flight inspired Wayne to sell insurance directly to consumers. (7:03) Why he reached out to a founder who tried (and failed) to launch an insuretech startup. (12:01) Becoming fluent in insurance industry jargon “was definitely a learning curve.” (16:05) The point when Wayne realized Sure needed to pivot. (20:16) The transition from D2C to B2B “was a slow aircraft carrier style turn.” (22:35) How to tell whether you're grinding through a rough patch or building on the wrong model. (29:21) When it was time to pitch to enterprise customers, “ most of those conversations were led by me. (32:40) “ Proofs of concept are actually the way for a big company to not do something.” (40:45) Sure is an embedded finance company, not an insurance company. (44:04) “ In hindsight, I would not want to be in another business where you are dependent on two other parties performing.” (49:08) The one question Wayne would have to ask the CEO if he were interviewing for a role with an early-stage startup. LINKS Wayne Slavin Sure "The Start-up From Hell," Inc.com SUBSCRIBE

James Joaquin is co-founder and managing partner at Obvious Ventures, a VC firm that backs startups tackling intractable problems like climate change, chronic disease, and income inequality.  Their portfolio includes businesses that once sounded like science fiction but are reshaping billion-dollar industries. He says he's looking for technology that will “move humanity forward." But this episode isn't just about mission-driven investing.  James gets extremely tactical: he breaks down how Obvious evaluates founding teams, how he prefers to be pitched, and how your answer to “why are you building this?” can make or break your shot at getting funded. He also shares a framework for balancing ego with humility, why startups die of indigestion — not starvation — and how his experience building one of Apple's most famous failures helped him identify category-defining companies. By the end of this conversation, you'll have a clearer understanding of what top-tier VCs are looking for—and whether your startup has what it takes to earn a “yes.” RUNTIME 46:38 EPISODE BREAKDOWN (2:37) James unpacks the firm's origin story: “We love to say that all great ideas are obvious in hindsight.” (7:43) What “world-positive” investing looks like in practice. (10:41) When it comes to a founder's domain expertise, “I  don't think that there's one single archetype.” (13:46)  What's something you used to believe as a founder that changed dramatically after you became an investor?  (15:15) “A lot of the work that I do at Obvious is trying to sniff through the veneer and the BS to get to that authenticity.” (18:13) The most successful founders he's bet on “were weird, and they were ridiculed by whatever industry they were in at the start.” (19:40) Tactical lessons he learned while working at Apple for six years after they acquired his startup. (23:29) Why generative science has “ become a key investment thesis” for Obvious. (26:48) James is looking for startups that will “ output or generate new scientific breakthroughs.” (29:42) “ You almost cannot think too large in terms of the scale that we're going after.” (33:03) James shares the framework Obvious used to evaluate geothermal startup Zanskar. (37:58) The firm's sweet spot: startups that are “just one step away from commercialization.” (42:31) “ We don't get lost in the noise of what's going to happen in the next three and a half years.“ (43:54) What kind of startup would he launch today if he wanted to change the world? LINKS James Joaquin Obvious Ventures Biz Stone Beyond Diamond Foundry Virta Health Zanskar Geothermal & Minerals Gusto Xoom What is a B Corp? (B Lab) SUBSCRIBE Get the newsletter Follow Fund/Build/Scale on Instagram Thanks for listening! – Walter.

Uncork Capital Partner Amy Saper shares practical advice for early-stage founders building AI-enabled tools for engineering, product, and design teams, or as she describes them, "products that make you not want to quit your job." Drawing on her experience in product marketing at Twitter, Uber, and Stripe, she explains why storytelling is an underrated founder skill, how to refine your ideal customer profile, and why it's good to reverse-engineer a roadmap from your Series A goals. She also shares tips for assessing founder/investor fit, when (and when not) to launch, and why she cares more about your conviction than your TAM slide. If you're a technical founder looking to pitch smarter, launch better, and scale leaner, this episode is for you. RUNTIME 40:46 EPISODE BREAKDOWN (3:46) How Amy's product marketing background informs her investor perspective (8:45) Storytelling skill (and coachability) “ separates the mediocre founders from the exceptional ones.” (12:02) “ I do tend to gravitate towards very technical teams. Sometimes they're all engineers.” (15:16) A few questions Amy would ask a VC if she were an early-stage founder (17:25) How she defines founder conviction — and the traits she looks for (22:56) Identify your goals and targets, then work backwards from there (26:55) “ I have a funny but also kind of real sub-thesis, which is products that make you not want to quit your job.” (28:50) Thanks to new AI tools, “ we're seeing the rise of small lean teams that are achieving early profitability.” (33:45) “ I am a sucker for a great deck or a beautiful presentation.” (36:30) “ I care less about the overall TAM than how you're defining what's addressable.“ (39:27) The one question Amy would have to ask the CEO if she were interviewing for a job with an early-stage startup LINKS Amy Saper Uncork Capital SUBSCRIBE

Ten Eleven Ventures CTO and Operating Partner Scott Lundgren shares practical advice for early-stage cybersecurity founders. He explains why founder-market fit matters more than product polish, how teams should think about TAM in fragmented markets, and the signals he looks for in technical pitches. He also breaks down how Ten Eleven's network helps with diligence and customer development — and why “cool tech” often misses the mark. Plus: his take on the AI hype cycle, and why building credibility starts with listening, not pitching. RUNTIME 38:06 EPISODE BREAKDOWN (3:37) How founding an ISP as a teenager led Scott to a career in tech. (6:06) Why he decided to join Ten Eleven Ventures as CTO/operating partner. (9:53) Scott breaks down the essential elements of a cybersecurity pitch. (14:31) Inexperienced founders, “as a general rule, have no idea about the TAM.”  (17:21) On AI hype: “ I'd like to see some more rigor with how we feel like we can start to quantify some of the benefits.” (20:20) Having a global network of security professionals is “ a really great resource for us as a firm, but also for our founders.” (21:51) Lessons learned from being on Carbon Black's founding team. (23:59) “ You need both of these things that are intertwined: the luck, and the the hard work.” (26:08) Do customer discovery face-to-face, not over Zoom. “It isn't always productive, but there's no substitute for it.” (30:57) Developing and promoting a startup mindset outside of Silicon Valley. (35:30) “ If you build really cool tech to solve a pretty simple problem, then that probably was over-engineered.” (36:11) How to build investor and future customer relationships — when you still have a job. LINKS Scott Lundgren Ten Eleven Ventures Carbon Black SUBSCRIBE

Construction workers spend hours on their hands and knees snapping chalk lines to mark where walls, plumbing and utilities should go. It's painstaking, back-breaking labor. And that's how it's been done for centuries. Tessa Lau saw an opportunity — and built a robot that does it faster, safer, and with surgical precision. In this episode of Fund/Build/Scale, the Dusty Robotics founder and CEO shares some of what she's learned about transitioning from a researcher to a deep tech founder, including: How she turned past startup mistakes into a rigorous customer discovery process The structured approach Dusty used to land its first paying customer Why she says stealth mode is overrated — and how building in public gave them a head start How “cool tech” can lead you astray if you're not solving a real problem Smart ways to pivot and iterate based on actual user feedback What it takes to build a mission-driven team that scales with you If you're interested in robotics, deep tech, or why some concepts fall into the valley of death while others sail over it like a Red Bull stunt team — listen in. RUNTIME 43:10 EPISODE BREAKDOWN (3:00) “ I always thought I would be a professor someday, and that was my planned career path.” (5:39) How a home renovation project led Tessa into making construction robots (9:16) “ We thought we were going to build a vacuum cleaning robot.” (12:24) “You have to establish that someone is willing to pay for the technology and that it's doable.” (14:15) “ We needed to build something that was 10x better than the status quo in order to scale at venture speed.” (15:41) Finding a deep tech TAM is “ a hard problem, especially when you're creating a new category.” (19:16) “ You can't try to be everything for everyone.” (21:00) Their first prototype “could barely do anything,” but fast pilots helped them iterate quickly. (26:08) How Tessa figured out their pricing *before* they went to market (29:24)  Why marketing and branding are table stakes for a deep-tech startup (33:11) “ As the CEO, you are the face of the company whether you like it or not.” (37:06) “ Our marketing team doesn't need to be very technically savvy.” (38:22) “ I have yet to see a good reason to be in stealth, ever.” (40:53) The one question she'd have to ask a deep tech CEO before accepting a job offer LINKS Tessa Lau Dusty Robotics Philipp Herget, CTO IBM Research Willow Garage, Wikipedia “Savioke is now Relay Robotics,” 5/2/2022, The Robot Report Crossing the Chasm, 3rd edition, Harper Books SUBSCRIBE

What happens when a team of legal veterans decides to rebuild the dispute resolution process from the ground up?  To find out, I interviewed Rich Lee, co-founder and CEO of New Era ADR, a platform designed to resolve legal disputes faster, at lower cost, and with less friction for both companies and individuals.  We talked about building a team that had enough credibility to sell into one of the most risk-averse industries, how they approached trust-building with both customers and investors, and how they're scaling a capital-efficient business in a category that's been largely unchanged for decades. Thanks for listening! – Walter. RUNTIME 39:46 EPISODE BREAKDOWN (2:59) “ I'm an early adopter of, you know, anything.” (10:03) “ The core problem: why does it cost so damn much to resolve a legal dispute in this country?” (13:05) How Rich and his co-founders divided roles and responsibilities (17:15) Hurdle #1: “ Challenging the underlying assumption that litigation and a legal dispute doesn't have to be two-plus years.” (22:32) In the early days, New Era ADR developed multiple personas to overcome customer objections (25:50) “ Fortunately, we didn't have to do a lot of POCs.” (29:40) “ Our market's comically big.” (30:03) Finding your SAM and SOM when the TAM is $350 billion (32:22) Which came first: the pitch deck, or the revenue model? (35:50)  One question Rich would have to ask the CEO if he were interviewing for a role with an early-stage startup. LINKS Rich Lee New Era ADR The Future of ADR? New Era Bags $6.3m While Still at Seed Stage, Artificial Lawyer, 3/16/2022 SUBSCRIBE

Before Postman became a category-defining platform used by millions of developers, it was a personal side project. In this episode, co-founder and CEO Abhinav Asthana shares how he went from hacking on API tools in Bangalore to leading a global company with nearly 900 employees across three continents. We talk about: Building a developer-first product that spread through word of mouth Choosing a CEO when everyone on the founding team is an engineer How to reach U.S. customers before you have a U.S. presence Why authenticity beats thought leadership when you're building in public Going from “ramen profitability” to Series A in just 17 months Whether you're an engineer who's thinking about starting something of your own, a founder operating outside of Silicon Valley, or just curious how Postman actually works, this episode is packed with tactical insights. RUNTIME 49:19 EPISODE BREAKDOWN (2:39) “ Being a developer who loved to hack and also design, I just decided to try my hand at this.” (4:00) “ We had a hypothesis, but we didn't have a company.” (6:08) Abhinav built goodwill with the developer community by being helpful (9:26) How they settled on the name “Postman” (11:51) On a team of engineers, how do you decide who should become CEO? (15:00) Who was their first key hire outside of the founding team? (20:15) Why he thinks early-stage startups should seek “ramen profitability” (23:23) “ Our first marketing hire was about two years in.” (25:18) What it was like to go from a seed round to Series A in just 17 months (30:02) “ At that point, it kind of became clear that this is a new kind of category.” (32:15) How Postman's branding dovetails with the platform's underlying technology (36:13) One thing he would have done differently in the run-up to the Series A (38:48) Managing cross-border growth when you're based in Bangalore (40:56) “ Building the company in two different places… it's just incredibly hard.” (44:47) “ Don't skimp on two things ever in starting a venture-funded company: your lawyer, and your accountant.” (45:52) One question he'd have to ask the CEO if he were interviewing for a job with an early-stage startup. LINKS Abhinav Asthana Postman Postman raises $50 million to deliver its API collaboration platform to more partners, 6/19/19, VentureBeat SUBSCRIBE

When Tony Stubblebine took over as CEO of Medium in 2022, the platform was burning $2.5 million a month, bleeding subscribers, and was overrun with content that left founder Evan Williams cringing.  Tony pitched Ev a turnaround built on small teams with access to data, customers, and the freedom to rebuild Medium like a startup from the inside out. He wasn't just another executive parachuting in — Tony had worked with him as head of engineering, later as a power user and publishing partner, and eventually, the person who convinced Ev that he could get things on track. In this episode of Fund/Build/Scale, Tony explains how Medium became profitable for the first time, why the platform banned AI-generated content from its partner program, and how his long history as a user and advisor uniquely prepared him to lead the company through a delicate transformation. RUNTIME 50:14 EPISODE BREAKDOWN (3:41) “ I have a long track record of being associated with Medium for just strange reasons.” (7:16) “ Maybe I'm crazy, but I thought on day one, ‘oh, this is a guaranteed win.'” (9:52) “ I think CEOs are delusional, and some amount of delusion is probably healthy.” (12:34) “ Precision is not possible without a combination of data science and user research or words.” (14:30) Creating customer feedback loops in a 13-year-old company (19:49) “ I would almost say there's no product to manage yet because we're making it, and we're making it together.” (20:17) The two mandates Evan Williams gave Tony when he hired him as CEO (24:23) “I  knew even if we could grow subscribers, it would be on the back of this content that we weren't proud of.” (25:45) Why Medium banned AI-generated content from its partner program: “ We're a pro-human product.” (30:11) “ We love human moderation. We love our trust and safety team.” (36:28) “ We're trying to be a place where a different set of writers will win on Medium than will win on these other platforms.” (40:46) “ One hundred percent: Medium is for experience, not for influencers.” (42:35) “ I really like to be a champion for what I would call ‘white hat content marketing.'” (46:45) “ It's wild to me that the art of blogging has not been perfected this many decades into it.” (48:17) “ It's impossible to understand how many niches there are.” LINKS Medium Tony Stubblebine Tony's Medium profile Mark Suster Cal Newport Flow: The Psychology of Optimal Experience, Mihaly Csikszentmihalyi SUBSCRIBE

Rachel Springate is the founding general partner of Muse Capital, an early-stage venture fund focused on overlooked sectors like women's health, wellness, parenting, gaming, and sustainability. In this episode, she shares her strategy for finding value where other investors aren't looking, explains how Muse assesses early traction in non-traditional markets, and breaks down the persistent funding gap facing women founders. We also discuss: How AI could transform women's health Why traditional VCs struggle to spot these opportunities What needs to change to solve the “2% problem” in venture capital Whether you're fundraising or building for an underserved market, this conversation offers tactical insights you can apply right now. RUNTIME 49:49 EPISODE BREAKDOWN (1:57) How Rachel connected with Muse Capital Founding Partner Assia Grazioli-Venier (3:43) Why “care, live and play” are the sectors they're most interested in (8:04) “ Entrepreneurs struggle in this space because typically the people that are building are female or diverse — building for their own.” (11:45) Many investors still don't recognize that women's health is a “ massive market opportunity.” (14:52) What are some of the signals that tell her a founder is ready to work with investors? (17:06) When it comes to domain expertise, “ our bar is pretty high.” (19:47) Muse Capital's process for analyzing market opportunities and evaluating founders (24:26) How seed-stage founders should prepare for their first VC meeting (27:10) “When a founder comes in and says, ‘nobody's doing what we're doing,' I'm like, ‘red flag.'” (29:33) When it comes to women's health, “ there's really interesting things that can be done with AI around unique data or proprietary data sets.” (34:44) How is the current political environment impacting innovation/investment in women's health? (37:44) Why less than 2% of venture capital goes to startups led by women (42:52) “ I do think we are going in the right direction. It's just gonna take a lot.” (44:45) How to get more women into the VC pipeline (47:45)  If you could snap your fingers today and change one thing about VC, what would it be? LINKS Rachel Springate Assia Grazioli-Venier Muse Capital SUBSCRIBE

Fredrik Thomassen, co-founder and CEO of Superside, joins the show to unpack how startups can scale creative work without slowing down or burning out their teams. Superside is a subscription-based design company that helps fast-growing teams get high-quality creative at scale. In this conversation, Fredrik shares how he built a globally distributed team, why async collaboration beats real-time meetings, and what most startups get wrong when managing creative work. We also get into: Hiring in overlooked markets Building customer trust and employee cohesion across time zones Structuring creative operations like a product team Why treating designers as partners — not vendors — drives better outcomes If you're juggling growth and messaging or just trying to build creative capacity without the chaos, listen in. RUNTIME 44:58 EPISODE BREAKDOWN (2:30) “ You start out and think, ‘I can do this for four or five years,' and all of a sudden, a decade has passed.” (4:32) Superside's beta was popular, but “ it was a total mess behind the scenes.” (7:36) Why “ it felt like an obvious move to go to YC.” (11:15) “ We found product-market fit, and then kind of COVID hit at the same time.” (14:17) The biggest mistake Fredrik made while adding headcount in the early days (18:59) Working with a founder coach has been “scary, but also in a sense, very motivating.” (21:39) Fredrik lists his preferred Norwegian authors (25:29) Inside Superside's pivot from freelancer marketplace to enterprise creative services (29:40) “ What's growing at the moment is AI-powered creative services for our enterprise customers.” (32:08) Quantifying the efficiency gai”s from using AI-enabled services (37:53) How Superside collaborates with clients to provide strategic services and production work (40:31) “ It's quite hard to build a lifestyle business.” (42:40) The one question he'd have to ask the CEO before accepting a job offer with an early-stage startup LINKS Fredrik Thomassen Haakon Heir Jing Venås Kjeldsen Superside Y Combinator Paul Graham essays Hunger, Knut Hamsun Jon Fosse Karl Ove Knausgård SUBSCRIBE

What makes a founder dangerous? Not credentials. Not their pedigree. And it's not who they know. For investor and former operator Promise Phelon, a dangerous founder is someone with lived experience, relentless conviction, and the ability to build something the world doesn't expect. Promise is the founder and managing partner of Growth Warrior Capital, an early-stage venture firm that invests in founders building seed and Series A enterprise AI companies. In this episode, she shares hard-won lessons from the founder's seat and the investor's table: how to turn capital scarcity into a strategic advantage, navigating the shift from founder to CEO, and why storytelling can't replace traction. We also talk about: How to find the investors who already have reasons to believe The “puzzle vs. mystery” framework for prioritizing execution What a dangerous founder pitch actually sounds like How underrepresented founders can cultivate an appetite for risk — without a safety net If you're building in stealth, raising without a network, or just wondering how to scale yourself as your company grows, this episode will give you a framework and some momentum. RUNTIME 59:08 EPISODE BREAKDOWN (04:32) Promise talks about her path from operator to investor (06:57) Inside Growth Warrior Capital''s investment strategy (09:25) What her typical work week looks like (14:01) “We love the qualitative, but our goal is to get to the meat of what's going on.” (16:36) How Promise prefers to be pitched (18:21) Growth Warrior Capital has plans for a second fund in the works (21:27) Why more founders need to evolve from being firestarters to fiduciaries (25:13) Where inexperienced entrepreneurs need the most help (28:13) “ We look for coachability in a founder. We also look for rigidity.” (30:50) “ A dangerous founder is someone that you don't expect to come up and kick you in the teeth.” (34:01) “ …So Kendrick Lamar is the soundtrack for every single investor meeting.” (36:09) What it's like to be pitched by a dangerous founder (39:30) One myth about successful founders that's holding people back (44:23) How to cultivate an appetite for risk when you don't have a safety net (50:41) What happens when founders learn to make bold strategic moves (53:09)  ”As a founder, you're not trying to convince anyone of anything. It's a search problem.” (57:14)  Something Promise used to believe about venture capital that is just totally untrue LINKS Promise Phelon Growth Warrior Capital Almanack of Naval Ravikant SUBSCRIBE

What kind of founder spends five years building a product before going to market? One who's trying to solve a very hard problem. Vince Gaydarzhiev is the founder of Alcatraz, a deep tech startup that uses facial authentication. The platform isn't used to lock people out of single offices or consumer gadgets; its customers are buying global enterprise security, where compliance is strict, trust is earned, and failure isn't an option. In this episode, Vince shares the emotional, strategic, and technical realities of building a company at the intersection of AI, hardware, and enterprise infrastructure. From working nights on prototypes with a tiny team to navigating founder isolation and breaking into risk-averse markets with no Silicon Valley network, Vince takes us inside the long game of building something real. We cover: Why it took three years to get a product into customer hands — and two more to scale it Validating a deep tech startup when you're not an insider What enterprise security leaders really care about (and how not to sell to them) Why founder empathy and “becoming your customer” are non-negotiable in this space The hiring philosophy that helped Alcatraz scale with high-agency, low-ego team members How Vince de-risked himself to earn trust from investors and prospective hires If you're building something technically ambitious or thinking about launching a startup in AI, hardware, or security, listen in. RUNTIME 32:15 EPISODE BREAKDOWN (2:35) Where the idea for Alcatraz came from and why Vince decided to take the leap (5:51) His process for validating the concept with investors, customers, and security teams (9:37) “I  was surprised that this thing didn't exist yet.” (11:48) Why it took five years to develop a “globally scalable” minimum viable product (13:29) How much has his TAM estimate changed since entering the market? (17:55) The pitch Vince used to recruit employees away from Apple and other top companies (20:05) “ In 2016, investors were investing into companies purely on a deck.” (22:18) “ I had zero network. It was my first time.” (24:42) “ Many people mentally cannot take ‘nos' in bulk. They get depressed, they feel it's personal.” (26:50) Why the name “Alcatraz?” (28:12) “ It's really tough to work with people that you don't like. Very tough. It's never gonna work out.” (30:24) The one question Vince would have to ask the CEO if he were interviewing at an early-stage startup LINKS Vince Gardarzhiev Alcatraz Alcatraz AI Raises $6.1M in Funding for Frictionless Access Control, 4/27/2021, press release Alcatraz AI Receives $25M Series A Funding to Accelerate International Growth, 9/13/2022, press release SUBSCRIBE

What turns a free trial user into a paying customer? For Ola Sars, founder and CEO of Soundtrack, the answer is all about behavior. In this episode, we break down how his team uses product-led growth (PLG) and product-qualified leads (PQLs) to drive conversions.  You'll hear how playing 100 tracks became a key signal for purchase intent, the tactics Soundtrack deploys to help self-serve customers experience value fast, and what it takes to scale a SaaS business in a market ruled by consumer giants. If you're building a PLG motion or trying to convert lookie-loos into cash customers, listen in. RUNTIME 45:20 EPISODE BREAKDOWN (3:11) “ It's 20 years now I've been trying to make a living here in the intersection of audio, music and technology.” (5:22) How Ola became a member of Beats' founding team. (9:37) Why he returned to Stockholm to build Soundtrack instead of remaining stateside. (13:38) When Ola started to learn about product-led growth. (15:38) “ It's a $40-50 billion market on an annual basis. And we're kind of the only company going after that market right now.” (18:54) “ We had this approach that everything had to be done self-serve.” (20:33) Creating a framework to ID and leverage product-qualfied leads (PQLs). (26:06) What role will AI play in music distribution and production? (28:23) The gaps Ola sees in today's music technology marketplace. (32:04) Why AI-generated music “ doesn't make any sense.” (35:03) Ola reflects on several cultural shifts that have made it “much easier now” to build in Europe. (38:12) Stockholm's entrepreneurs are “kind of hybrid Americans in a way how we think about business.” (42:08) The biggest myth Americans believe about starting up in Europe. (44:09) If you were interviewing for a job with an early-stage startup, what's one question you'd have to ask the CEO before you could accept an offer? LINKS Ola Sars Soundtrack B2B music streaming service Soundtrack Your Brand raises $15 million, Tech.eu ​​What is “lagom?”, Study in Sweden The English term "mid" matches the Swedish term "bland, mellan,” tok-pisin.com SUBSCRIBE

Mike Conover started his career as a machine learning engineer. Today, he's the co-founder and CEO of Brightwave, an AI startup helping financial professionals make faster decisions with massive, unstructured data. In this episode of Fund/Build/Scale, Mike shares how he made the leap from technical contributor to strategic leader—and the hard lessons he learned along the way. From translating technical vision into a focused go-to-market strategy, to learning how to coach, hire, and scale intentionally, Mike unpacks the mindset shift required to move from building code to building a company. We also get into: How Brightwave validates new product bets in a high-stakes industry Why founder-market fit is emotional, not just strategic Mistakes to avoid when hiring your early team How to create focus loops and feedback channels before feature creep sets in Why emotional intelligence and execution velocity matter just as much as AI architecture If you're a technical founder — or thinking about becoming one — this conversation offers an unvarnished look at what it actually takes to scale yourself while scaling your startup. RUNTIME 55:09 EPISODE BREAKDOWN (1:12) Mike explains how Brightwave works. (3:49) Where the idea came from. (7:47) How he connected with co-founder Brandon Kotara. (10:58) The biggest challenges he faced shifting from an engineering role to founder/CEO. (14:22) “As a CEO, you have to do a lot of jobs that you have no preparation for.” (15:07) Working with a coach has been “such a sustaining source of inspiration, but also continuity.” (18:45) “There's a rap lyric I really like, which is, ‘you can't crush me, I'm dirt.'” (20:29) Turning “reasonable” feature requests into new products helped Brightwave build customer trust. (25:30) “ It's unusual,” but co-pilots and POC programs were not part of their early success. (30:12) Tips for building feedback loops between customers and the product team. (36:04) Seed to Series A “ was about four months.” (40:02) “ Most startups are not that defensible.” (45:54) “A lot of the product-led growth techniques that you might use don't always fit the market especially well.” (47:45) How to create a self-assessment framework for founder-market fit. (50:43) “ Brightwave — in its full totality — has material substance in my mind already.” (53:05) The one question he'd have to ask the CEO before taking a startup job. LINKS Mike Conover Brandon Kotara Brightwave Fred Kofman, Conscious Business SUBSCRIBE

Igor Taber has sat on both sides of the table: first as a VC at Intel Capital, then as an operator at high-growth AI startup DataRobot. Now, as co-founder of Cortical Ventures, he's backing the next generation of AI-first startups. In this episode, Igor shares how his operating experience reshaped his investment lens, what most VCs still miss about early-stage execution, and how founders can break through the AI noise to build something that actually lasts. We also get into: What it really takes to build conviction at the seed stage How Cortical Ventures defines “defensibility” in AI The questions every founder should ask an investor (but usually doesn't) Why your biggest advantage may not be your model — it's your momentum If you're building in AI, fundraising, or trying to turn early traction into a long-term advantage, download this episode. RUNTIME: 39:52 EPISODE BREAKDOWN (1:19) Igor: My investor-operator-investor path was “ a really interesting progression.” (3:33) Previously, a lot of his opinions were rooted in the “VC echo chamber.” (6:56) “ You just try to do your best to be a good partner and be helpful.” (7:43) Why he and co-founder Jeremy Achin started Cortico. (13:39) What makes an early-stage AI team stand out? (17:15) When it comes to solo vs. team, “ we haven't seen any like material difference in outcome.” (18:56) “ I think the biggest company on LinkedIn is called ‘Stealth.'” (22:17) Why TAM isn't a major consideration when evaluating new opportunities. (24:18) His framework for evaluating and validating seed-stage startups. (26:03) The biggest red flags in founder discovery meetings. (28:21) Top mistakes founders make in the first year after closing a seed round. (33:16) How Cortical advises AI founders to build more resilient companies. (35:55) A few things to keep in mind before quitting a secure job to launch a startup. (38:07) How to make yourself more investible in 2025. LINKS Igor Tabor Jeremy Achin Cortical Ventures SUBSCRIBE

Runway CEO and co-founder Siqi Chen shares how his team used a waitlist not just to build hype, but to engineer smarter growth. In this episode of Fund/Build/Scale, Siqi breaks down how Runway strategically kept customers in a holding pattern to gather feedback, qualify demand, and refine product-market fit. We also talk about: How to build trust with early users through transparency Using scarcity and access control as GTM levers Why financial planning should be accessible to everyone on the team What most founders get wrong about burn rate and cash flow Whether you're in the early stages or prepping for launch, this episode offers a masterclass in thoughtful, tactical go-to-market execution. RUNTIME 39:46 EPISODE BREAKDOWN (2:49) “ What if somebody worked on a Figma for finance?” (5:48) “ You have to understand what are the different levers of the machine, and how the machine works.” (8:50) Why Runway represents a cultural shift in corporate transparency. (11:51) How much financial literacy should founders try to foster across their organizations?  (14:48) How much runway should a startup aim for? (18:39) How Runway's waitlist fed directly into its GTM strategy. (21:36) The  ”very simple motivation” behind creating the waitlist. (24:35) The “negging trick” that makes sales prospects want to buy your product. (26:37) “ Your early customers join you for very different and specific reasons.” (28:55) “ Our first website, we didn't even really talk about the product.” (30:23) After opening up the waitlist, “ nothing really changed — we were doing outbound sales already.” (34:17) “People who are really motivated by your purpose and mission are willing to give you a lot more leeway.” (36:42) What the next five years could look like for Runway. (38:07) The one question Siqi would ask a CEO if he was interviewing at an early-stage startup.  LINKS Siqi Chen Runway Runway lands $27.5M to streamline financial planning for businesses As Not Seen on TV, Pete Wells, NYT Restaurant Review, 11/13/12 SUBSCRIBE

Ayelet Noff has spent more than two decades helping startups land meaningful press — but she's also seen how the game has changed. In this episode of Fund/Build/Scale, the founder of SlicedBrand and new PR tech startup Dazzle shares what still works, what doesn't, and how founders can earn meaningful attention in today's fractured media landscape. We get into: – What makes a pitch actually land with reporters – How to build credibility before you have traction – The biggest mistakes founders make when trying to “get press” – How AI tools are shaping the future of PR Whether you're early-stage or scaling, this episode is packed with practical advice for telling your story with clarity and credibility. RUNTIME 49:49 LINKS Ayelet Noff @AyeletNoff (X) SlicedBrand Dazzle SUBSCRIBE

Sahitya Senapathy, founder and CEO of Endeavor AI, joins Fund/Build/Scale to talk about launching a solo-founded startup at the intersection of AI and heavy industry. From building FEMA apps at age 11 to raising $7M before finishing college, Sahitya shares the hard lessons behind the headline. We dig into: – Selling AI solutions to manufacturers with no network and no co-founder – What enterprise customers actually care about in early-stage tech – Navigating credibility as a first-time founder in hard tech – Building while still learning — on the floor, in the pitch, as a leader This is a candid look at what it means to hustle in deep tech without shortcuts or safety nets. RUNTIME 46:18 LINKS Sahitya Senapathy Endeavor AI Forward deployment model SUBSCRIBE

Sophie Bakalar, partner at Collaborative Fund, joins Fund/Build/Scale for a candid conversation about early-stage investing in climate tech, consumer AI, and deep tech hardware. She shares how she evaluates “green” founders with limited experience, what kind of traction she looks for in pre-revenue companies, and why a passion for solving a real-world problem outweighs having a stacked resume. We also cover: Tactical funding strategies for capital-intensive startups The value of adaptable teams and fractional CFOs How to avoid overspending before product-market fit The mindset shifts needed before approaching VCs This episode is packed with advice for founders navigating long development timelines, technical risk, and early go-to-market strategy — especially if you're looking to raise money while keeping burn low and momentum high. RUNTIME 48:59 EPISODE BREAKDOWN (2:24) “Like a lot of people in venture, I have sort of a windy path.”   (6:47) Inside Collaborative Fund: “We all roll up our sleeves on everything here.”   (7:55) Which industries and founder profiles Sophie is watching in 2025.   (10:37) Where consumer AI hardware may be headed.   (12:03) What her typical work week looks like.   (15:05) In a people-driven industry, inexperienced founders need to de-risk themselves before doing investor outreach.   (17:37) “We don't necessarily create a hard line or a clear box around what makes a climate tech investment.”   (22:43) “There are a few things that investors in climate and energy tech are looking for.”   (26:23) When it comes to solo founders, “expectations from funders [are] a little bit higher.”   (28:28) What excites Sophie about working with first-time founders.   (30:17) The most common reason why a team with a strong idea fails to execute.   (33:31) Why a founder's “adaptability quotient” is so critical to their success.   (36:53) Personalities (and business models) that should avoid venture capital.   (40:16) “I hope I've managed to retain a good amount of empathy.”   (42:11) One piece of advice for VCs she returns to frequently.   (44:37) “The only real seismic changes are going to happen when you start to see more female entrepreneurs build really successful companies.”   (46:52) The blogger you need to read “before you kick off your fundraise.”   (47:39) The one question Sophie would have to ask a CEO before accepting an offer from an early-stage startup. LINKS Sophie Bakalar Craig Shapiro Collaborative Fund Fred Wilson, AVC archive SUBSCRIBE

Recorded in July 2024, Aimi founder Edward Balassanian joins Fund/Build/Scale to share how his AI-powered platform creates generative, copyright-safe music for enterprise clients. He explains how customer discovery with DJs shaped Aimi's tech, why compliance is core to their strategy, and why the company downsized after hitting product-market fit — all while inventing a market where AI music solves problems humans can't. RUNTIME 30:47 EPISODE BREAKDOWN (4:17) “ I consider myself a platform person. I build operating systems.” (7:39) “ It's incumbent on a founder in a space like this to be well-versed in not only the art of the music, but the science of the music as well.” (9:14) “ We see a song as a medium between fans and artists. We're not in the song business.” (11:03) How Aimi is building a library of licensed content: “We've been pretty methodical.” (14:59) “ We see ourselves as kind of uniquely in the business of music AI for creation, not for imitation.” (16:46) “ We de-risk the use of music. That's one of the biggest selling points for enterprise customers.” (18:44) “ Like most tech people, I would say we're always going to be in beta.” (21:58) Why Aimi raised its $20M Series B in 2021. (24:01) Downsizing after reaching PMF “ was the best decision that we that we could have made.” (28:05) “ I think what's really interesting is building platforms, and any platform today is going to have to incorporate AI into it.” LINKS Edward Balassanian (Crunchbase) Aimi AI-Powered Music Platform Aimi has raised $20 million in a Series B round of funding SUBSCRIBE

In this episode of Fund/Build/Scale, Nectir co-founder and CEO Kavitta Ghai shares how she turned her frustration as a college student into a fast-growing, VC-backed edtech startup. Kavitta discusses the leap from student to founder, how she built an AI-powered tool for classrooms without a technical background, and the tactics that helped her and her co-founder land paying customers early. She also opens up about navigating the venture world as a first-generation founder and reframing risk as a competitive advantage. RUNTIME 59:59 EPISODE BREAKDOWN (1:57) “ One day we said, ‘what if we stopped complaining and we actually did something about it?'” (5:57) “ The idea for Nectir initially just sort of fell into my lap.” (10:29) “ I was a communication major. He was an environmental studies major. We had no technical background at all.” (12:50) “ To go from a broke college student to being a broke founder really doesn't feel like that big of a difference.” (14:12) How they landed Nectir's first customer — UC Santa Barbara. (20:50) “ We have this philosophy that I call our ‘zones of genius.'” (23:46) Why customer discovery should “ every single person on the team for as long as you possibly can.” (27:03) “ When I go back and think about what we did best in that beginning period of time, it was starting with a very basic MVP.” (30:47) “ It was a huge surprise and it was terrifying when I realized, ‘oh shit, I'm the salesperson.'” (34:47) Kavitta shares her top recommendation for free founder advice — and one she had to pay for. (38:43) “ I actually came into building Nectir with zero understanding of what VC funding even was.” (43:38) “ You have to be willing to ask for what you want and it's the only way to get it.” (47:24) “ Right this second is the best possible time to start your company.” (51:50) “ It's not the thought of me sitting on a yacht one day that motivates me.” (53:09) Nectir's pilot program with the California Community College system. (56:49) The one question Kavitta would have to ask a CEO before she'd take a job at their startup. LINKS Nectir Kavitta Ghai kavitta.com How to Crash the Silicon Valley Party California Community Colleges Launches Groundbreaking Pilot with Nectir AI Paul Graham essays What is FERPA?, U.S. Dept. of Education Entrada Ventures SUBSCRIBE

Would you leave a stable, high-paying job at Google to build something that competes with NVIDIA, Intel, and AMD? That's exactly what Tim Davis, co-founder and president of Modular, did. Since then, his company has raised $130M to reimagine AI compute infrastructure — but are AI startups really desperate for a new compute layer? And what's it like to build a startup when your biggest competitors are trillion-dollar giants? In this episode of Fund/Build/Scale, Tim shares his vision for the future of AI compute, why talent is the real key to success, and some of the tough lessons he's learned from three startups. RUNTIME 46:27 EPISODE BREAKDOWN (1:26) “We are building a new accelerated execution platform for compute.” (6:41) “ It will exist all over the place and it already does, but AI will be everywhere that compute is.” (11:18) “ You only you only have so much time in a week. What is the thing that you're best at?” (15:13) “ We have decided to start from the hardest part of the software stack.” (22:44) “For the most talented people in the world, the risk is actually not as great as what you think.” (30:24) “ Growing up in Australia, my view of the of the United States was very much driven from the media and from Hollywood.” (33:26) “ I sat in a room for six weeks and just met everyone that I could. And that really was the beginning of a journey to the United States.” (37:48) “ I still think there's a special place in the Bay Area, and in the United States, there is a different risk appetite.” (40:41) The one question Tim would have to ask the CEO before he'd take a job at someone else's early-stage startup. LINKS Tim Davis, co-founder, president timdavis.com Chris Lattner, co-founder, CEO Modular AI startup Modular raises $100 mln in General Catalyst-led funding, 8/24/2023, Reuters  SUBSCRIBE

Building a startup in Europe presents a unique set of challenges, like fragmented markets, cultural differences in risk-taking, and a VC ecosystem that's still maturing compared to Silicon Valley. But things are changing fast. For this episode of Fund/Build/Scale, I sat down with Lucile Cornet, partner at Eight Roads, a global VC firm that invests across Europe. We dive into:

Journey founder and CEO Stephen Sokoler appeared on Fund/Build/Scale in June 2024 to talk about how his startup pivoted from B2C meditation services to a B2B mental health platform, along with what that shift revealed about selling to enterprise clients. He breaks down the challenges of high customer acquisition costs, the trade-offs of venture capital, and the key lessons founders should know before making a major business model shift. RUNTIME 38:28   EPISODE BREAKDOWN (2:20) Why Stephen decided to found Journey — identifying the need for accessible mental health solutions. (5:07) “We probably had five or six different products that worked and didn't work until we got to where we are today.” Lessons from early iterations and failures. (7:32) Pivoting to B2B “was definitely a safer bet than to continue doing consumer, which just seemed like a dead end.” (9:26) Landing early customers like Warby Parker — how this helped de-risk Journey for enterprise clients. (11:37) Why he sought out venture capital in the company's early days — and what he learned from the process. (13:56) Knowing what he knows now, would he still have pursued VC? (17:11) Reaching product-market fit “changes the fundamentals of the business significantly.” (19:00) “One of our core pillars is that it's a global offering rooted in diversity and inclusion.” (23:17) We think it's really important to make mental health part of the fabric of working at a company, versus a random benefit.” (25:17) The three key data points Journey tracks to measure impact and effectiveness. (28:25) “You can decide: Do you want it to be a lifestyle business? Do you want it to be a unicorn?” (31:49) Work-life balance vs. work-life integration — “I don't like the term ‘work-life balance,' because then it feels like something's always kind of out of whack.” (34:29) How Stephen has learned to manage the mental toll of entrepreneurship. (37:25) “Not every business should be a venture-backed business.” Key insights on whether VC is the right path. LINKS Stephen Sokoler Journey   SUBSCRIBE  

When you accepted the offer, maybe you imagined being in the group photo when your boss rang the bell at NASDAQ. But five years later, your company just raised its Series C, and an IPO isn't on the horizon. Meanwhile, you need liquidity — whether it's for a down payment on a house, starting a family, or another major life event. The stock options you've earned are fully vested, but they're just sitting there. So how do you turn them into cash? If your company allows it, you can sell your shares to an accredited investor, assuming you can find a buyer who'll meet your price. That's where the secondary market comes in. I spoke with Phil Haslett, founder and Chief Strategy Officer at EquityZen, a platform that helps startup employees sell a portion of their equity to investors looking to get in on high-growth companies before they go public. We took a deep dive into how the secondary market works, its risks and rewards, and how aspiring founders can even use it to bootstrap their own startups. Disclaimer: This interview is for informational purposes only. Nothing Phil says should be interpreted as financial advice. RUNTIME 41:54 EPISODE BREAKDOWN (0:00) I used Descript to create an elaborate cold open for this episode, please listen. (3:19) The specific pain point that led Phil and Atish to start EquityZen. (5:11) “ I've kind of gone through maybe two or three evolutions of the IPO markets since EquityZen started.” (7:57) All things being equal, early-stage tech workers take on more risk than founders or investors. (9:12) Few workers are well-informed about the secondary market, “but it's not their fault.” (11:38) “ At some point, employees start to decide that maybe where they want to work — or maybe where they want to keep working — might be informed a bit by what they can or can't do with their equity.” (13:06) Should we keep the traditional four-year vesting schedule, or scrap it for something new? (14:14) Typical reasons why sellers turn to the secondary market. (16:25) EquityZen's typical selling size and average investment size, as of November 2024. (18:52) ” You're probably not gonna get a billion-dollar valuation for your shares purely based on structure alone.” (20:45) Keep close track of your equity, especially if you think you're going to be laid off. (22:20) Consult a financial services professional before you start the process. (24:16) “ The first steps are kind of just also learning if you can sell your shares.” (27:04) “ The company that you held shares in, if it went to zero: would you regret that you didn't sell?” (30:10) A framework for figuring out whether the secondary market is worth the time and trouble. (33:25) Offer your employees liquidity without jeopardizing morale or financial stability. (36:27) Phil's founder pitch: “ We're gonna support you all along the way. We can help you with liquidity in the future.” (39:16) Tips for approaching your CEO to ask about liquidity options. LINKS Phil Haslett, co-founder/Chief Strategy Officer Atish Davda, co-founder/CEO EquityZen Descript stock library: Music: She Was In Hawaii (Lap Steel) SFX: Bar Background Ambience 01 SFX: Ocean Waves Crashing Ambience SUBSCRIBE

Do you want to know the difference between marketing and PR? Marketing is when you say something nice about yourself; PR is when other people say nice things about you. Jenna Guarneri is the founder of JMG Public Relations and author of the bestseller "You Need PR." In this episode, she shares DIY PR tactics that help founders establish themselves as experts, attract customers, and raise their profile with investors — without spending a fortune on an agency. If you've ever wondered why reporters never get back to you, we cover that, too. Key takeaways from this episode: ✅ Why PR comes before PMF in the startup playbook ✅ The biggest PR misconceptions founders have (and how to avoid them) ✅ How to craft a media pitch that actually gets responses ✅ DIY PR strategies for building credibility before you hire a firm ✅ The right way to engage with journalists without being ignored ✅ How PR can help secure funding and drive startup growth If you're trying to take control of your PR strategy and attract positive attention, listen in. RUNTIME 31:28 EPISODE BREAKDOWN (1:52) How Jenna sets client expectations on what PR can and cannot accomplish. (5:14) Key signals that indicate an early-stage startup is ready to hire outside PR. (6:41) “The founders usually are amenable to PR and doing media interviews. It kind of comes with the territory of being a founder.” (7:59) How to get started with DIY PR by sharing thought leadership that creates value. (11:35) “PR should be done at the very beginning, right from the very start.” (12:20) The right way for stealth startups to approach PR. (13:02) The top reasons why reporters ignore pitches — and how to avoid them. (15:21) Crafting a news hook that genuinely engages journalists. (17:33) How your world changes when PR starts working. (18:50) “Effective public relations will drive the business in a number of ways.” (20:50) How to interview and vet a PR firm before making a commitment. (22:46) PR is a long game: “We can't work miracles in three months.” (25:22) Why using ChatGPT to pitch reporters is a terrible idea. (27:42) “Content creation does take a lot of time, a lot of energy, but it goes a long way really quickly for brand awareness.” (30:14) The one question Jenna would have to ask before hiring a PR firm. LINKS Jenna Guarneri JMG Public Relations You Need PR SUBSCRIBE

Building a startup in Africa isn't the same as doing it in Silicon Valley. Some challenges overlap, but many don't, like currency volatility, limited early-stage funding, and investors who expect you to scale faster than the market allows. So how do you grow beyond your home market? How do you raise funds when VC is scarce? And what do African founders need to do to make their startups more venture-backable? To find out, I spoke with Mobola da-Silva, a partner at Capria Ventures who's based in Nairobi, Kenya. She's been investing in Africa and other emerging markets for nearly two decades and knows exactly what separates startups that thrive from those that stall. She shares practical insights on navigating currency risk, securing funding, and preparing for Series A — even if you don't have a deep-pocketed network to lean on. If you're an African founder trying to build a company that investors take seriously, this episode is for you. RUNTIME 46:19 EPISODE BREAKDOWN (2:03) How Mobola got her start in VC and the path that led her to Capria Ventures. (4:09) Capria Ventures' investment thesis. (5:32) The regions and sectors where generative AI is creating real value. (10:41) The best way to pitch Capria Ventures — and what investors want to see. (12:26) “A venture-backable business has to be able to achieve significant scale.” (15:13) “We're getting a bit more creative in Africa around funding for startups.” (16:20) How currency volatility impacts valuations — and strategies for mitigating risk. (22:18) “To pitch successfully, you have to be able to tell a story, right?” (23:51) Why Capria Ventures avoids solo founders and what investors look for in teams. (28:33) “Many investors don't think of product-market fit as a binary thing.” (31:29) The key metrics that signal true product-market fit. (33:49) “Make sure that you have a strong business before you try to start to move it to another market.” (37:49) “Silicon Valley looms larger than life in Africa.” How founders should interpret this influence. (42:46) Mobola's top advice for early-stage founders in Africa looking to scale and raise capital. LINKS Mobola da-Silva Capria Ventures Investment inquiries SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Eric Ly is the CEO of KarmaCheck, where he's tackling a problem he first noticed years ago as a co-founder of LinkedIn: People don't always tell the truth about themselves. To address this, KarmaCheck — launched in 2019 — automates key aspects of the background check process. By reducing complexity, employers can speed up hiring, while job applicants experience less friction along the way. “This is one of the first touch points with the employer: experiencing pain and frustration having to go through this process,” said Eric. “For us to show up with something new and different and better was frankly a breath of fresh air for the employers, the customers that we work with.” In this episode, we discuss: Jumping into a highly regulated industry with no prior domain expertise Why customer discovery should focus on patterns, not one-off insights The benefits of selling new features before they exist How to balance customer requests without losing focus We also talk about stepping out of LinkedIn's shadow, resisting the temptation to build for a single customer, and knowing when to say “no” to feature requests. RUNTIME 40:20 EPISODE BREAKDOWN (1:37) “Several years ago, I became really interested in this whole concept around trust and trust online.” — How Eric first recognized the problem that led to KarmaCheck. (3:22) Entering a highly regulated industry without prior experience — where Eric found the confidence to take the leap. (5:30) A look back at KarmaCheck's first hires — who they brought in early and why. (6:47) How KarmaCheck convinced early customers to take a chance on an unproven solution. (10:36) “Where employers don't even meet the people that they interview in person, there's an opportunity for the wrong things to happen.”  (12:21) “We identified a pain point in corporate America that people often experience frustration with.”  (14:34) How Eric used early customer feedback to shape KarmaCheck's product strategy. (16:11) The role of proof-of-concept programs in building customer trust. (21:16) “Make sure that whatever you commit to in your product is going to be applicable for more than one customer.”  (24:47) When customer feedback leads you down the wrong path — how to recognize it and recover. (27:46) Why it's important to keep track of rejected product ideas.  (29:49) The lessons from LinkedIn that Eric chose not to apply at KarmaCheck. (32:54) Advice for founders who want to step out of a shadow and build something completely new. (35:54) How to find a mentor when you don't have a built-in network — Eric's tips for making meaningful connections. (38:24) The one question Eric would ask a CEO if he were interviewing for a job at an early-stage startup. LINKS KarmaCheck Eric Ly KarmaCheck Raises $45 Million Series B to Modernize Background Checks and Credentialing (Press release. 6/27/2024) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Most early-stage founders I talk to are focused on getting their first customers, hiring their first employees, or maybe, if they're lucky, closing their first round of funding. But what happens after that? For Rohit Choudhary, the answer was building a whole new category. Rohit is the CEO and co-founder of Acceldata, a data observability platform that helps companies manage the complexity of modern data infrastructure. Before starting the company, he spent years inside the problem — working on data engineering challenges at Hortonworks and other enterprise tech firms. Like a lot of technical founders, Rohit didn't start out dreaming of being a CEO — but the problem was too big to ignore. In this episode, we talk about: Why data engineering lacked the right tooling and how that led to Acceldata How his team validated the concept with real-world customer pain points The trade-offs of building in stealth mode vs. in public What he's learned about hiring, scaling, and making the leap from engineer to CEO If you're trying to figure out how to go from technical insight to scalable business, this one's for you. RUNTIME 37:37 EPISODE BREAKDOWN (2:16) “ There are four of us co-founders, and we were all part of the same engineering team at Hortonworks.” (4:33) “ We felt that here was a unique opportunity for us to be able to build something really, really large and big.” (6:16) How Acceldata approached proof-of-concept programs in its early days. (8:23) “ How did you decide which one of you would become the CEO?” (11:31) Rohit's seed-stage recruiting strategy: “ we had to excite them with the long-term vision.” (14:35) “ People like me, we learned how to sell despite coming from an engineering background.” (16:46) Why the co-founders “took a leap of faith” by formalizing their sales process early. (18:46) “ We were familiar with how business is conducted in the U.S.,” which made expansion easier. (21:08) Early challenges they faced after closing a Series A. (23:08) How “a big mistake” from a previous startup still influences Rohit's choices today. (25:30) Wondering if it's time to throw in the towel? Do a self-assessment. (28:31) Three core skills engineers need to acquire if they want to become effective CEOs. (31:39) “ I used to interview almost everyone until we were at about, you know, 170-180.” (33:82) How creating a 10-year strategy informed their day-to-day decision making. (36:27) The one question he'd have to ask the CEO in an interview before he could accept an offer. LINKS Acceldata Rohit Choudhary, co-founder/CEO Ashwin Rajeeva, co-founder/CTO Gaurav Nagar, co-founder/Senior Architect Raghu Mitra Kandikonda, co-founder/Director of Engineering Lightspeed Venture Partners Acceldata Announces $50 Million in Series C Funding to Expand Market Leadership and Product Innovation in Data Observability (press release) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Startups face unexpected risks every day — cyberattacks, lawsuits, market shifts —but many entrepreneurs don't think about risk management until it's too late. In this episode of Fund/Build/Scale, Vouch co-founder/CEO Sam Hodges explains why risk management should be top of mind for early-stage founders. We discuss: Why risk management matters for early-stage startups   How Vouch validated, built, and launched Corix as a new business unit   The biggest mistakes founders make when managing risk   Why work-life balance is a myth for startup leaders   Key insurtech trends that early-stage founders should watch in 2025   Sam also shares insights on team structuring, branding, and time management—plus the one question he'd ask an insurtech CEO before taking a job. RUNTIME: 44:36 EPISODE BREAKDOWN (2:27) “ Risk management is something that a lot of founders don't think about a lot, but when it matters, it really matters.” (3:26) How Sam connected with co-founder Travis Hedge. (5:53) Why Vouch's first team member was a design lead. (6:35) What sets Corix apart from Vouch's core offerings. (9:05) The process behind starting up a new business unit. (12:42) “ At some point in scale, almost every company is going to organize around products, geographies, or market segments.” (15:05) “ There are three very specific stakeholder groups that we talk to all the time.” (16:26) How the team balanced quantitative metrics against qualitative insights while planning. (18:50) Inside their messaging, branding and rollout strategy for Corix. (21:59) “ The roots of Corix are ‘core' and ‘risk,' and we really do think that's what this is all about.” (25:47) How Sam's day-to-day work is different since launching a new BU. (28:25) A few thoughts about time management and self-care. (30:32) “ I am not a big fan of the term ‘work-life balance.'” (33:22) “ When you make a decision like this, it is going to always feel like it is too early or too late.” (35:48) Insurtech trends early-stage founders should look out for in 2025. (40:14) The biggest risk-management mistakes Sam sees founders making. (43:14) The one question he'd have to ask an insurtech CEO if he were interviewing for a job. LINKS Vouch Sam Hodges, co-founder/CEO Travis Hedge, co-founder/CRO Introducing Corix: An MGA from Vouch, Empowering Brokers with Tailored Insurance Products (PR Newswire) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening!   – Walter.

Amr Awadallah is the CEO and co-founder of Vectara. Previously, he co-founded Cloudera, which went public in 2017 and was acquired for $5.3 billion, and also served as VP of Developer Relations at Google Cloud. His first startup, Aptivia, was acquired by Yahoo, where he later became VP of Product Intelligence Engineering. I talked to him about his experience as an immigrant in Silicon Valley, the frameworks he's built to articulate vision and credibility, and what he's learned about pitching investors and recruiting top talent over the years. Runtime: 52:43 EPISODE BREAKDOWN (3:39) “ The more technical definition of what we do is ‘RAG as a service.'” (5:38)  ”You ask your car, ‘why is this icon showing, what's wrong with you?' And the car will tell you, hey, you need to go change my oil.'” (8:07) What makes Vectara a blue-ocean company. (10:05) How to win an investor's confidence when your current TAM is zero. (12:04)  ”There's three things anybody looks for when they're going to join any job, and you need to at least win two of the three.” (15:06) How Amr connected with the other Vectara co-founders. (17:24) Why he's “a very big opponent to building in stealth.” (21:50) Attending Stanford helped Amr visualize himself as an entrepreneur.  (24:34) “ Many entrepreneurs think that the idea is what's going to make a company succeed or not.” (28:54) How he cultivated an appetite for risk again after spending eight years at Yahoo. (32:44) “ Only get the PhD in one case, and one case only: if you want to be a professor.” (37:35) “ By definition, more immigrants will be more willing to take risks.” (41:33) “ There's so many VCs out there pretending they're amazing.” (43:54) There are two types of salespeople: “coin operators” and “innovators.” (48:20) You can start up outside Silicon Valley, but “ if you can move here, move here.” (50:27) Two questions he'd ask the CEO if he were interviewing for a job with a new startup. LINKS Amr Awadallah Vectara Cloudera Google Cloud SUBSCRIBE LinkedIn Substack Instagram Thanks for listening!   – Walter.

In this episode of Fund/Build/Scale, I talked with YL Ventures Partner Andy Ellis (a former CISO) about his approach to storytelling, tactics for founder-led sales and marketing, and why he thinks the cybersecurity hiring challenge isn't a talent shortage, but a market misunderstanding. We also discussed refining product-market fit, customer discovery methods and pitfalls like believing in one's own narrative too strongly. The conversation also touched on hiring strategies, managing design partnerships, and maintaining humility as a founder. “The basic entry level skill of reading the room is knowing when somebody already agrees with you,” said Andy. RUNTIME 44:15 EPISODE BREAKDOWN (1:44) Andy describes his day-to-day work at YL Ventures with founders. (4:08)  "It's like you now have an infant, and your only job as a parent is to create a competent adult.” (6:33) How he prefers to be pitched. (7:52)  ”The art of storytelling is taking a message and putting it in a narrative vehicle.” (14:38) The biggest storytelling mistakes early-stage founders make. (17:08) “ The basic entry level skill of reading the room is knowing when somebody already agrees with you.” (18:50) “ Fear is a hard, hard sale… It's so transparent and CISOs do this every day.” (19:36) Common cybersecurity GTM missteps. (21:40)  ”The moment that you can sell the same product to two different companies, you should have a sales rep.” (23:45) How Andy helps founders read the room when they're trying to make a sale. (27:20) “ You're hiring really out of a very different pool when you're in the cybersecurity space.” (29:08) “ Stealth is sort of a misnomer, but we're still sort of stuck in it.” (30:54) What to say if you want someone to quit their cushy job and join your risky startup. (32:46)  Rock-star hires are “fantastic if they stumble into your lap, but you can't go look for them.” (35:08) “ That first marketer you hire needs to be able to do a lot of things.” (39:05) “People with massive egos have a lot of humility.” (41:20) Trends in cybersecurity and AI he's excited about in 2025. LINKS Andy Ellis 1% Leadership: Master the Small, Daily Improvements that Set Great Leaders Apart csoandy.com YL Ventures YL Ventures' The State of the Cyber Nation 2024 (PDF) SUBSCRIBE TO FUND/BUILD/SCALE LinkedIn Substack Instagram Thanks for listening! – Walter.

Two of the three co-founders of Operant AI — CTO Dr. Priyanka Tembey and CMO Ashley Roof — joined me to talk about building the first runtime application protection platform and navigating the challenges of cloud-native security. The company announced a $10M Series A in September 2024 — In October, we discussed taking the leap into entrepreneurship, the lessons they learned through customer discovery and education, making early hires count, and the importance of early-stage team dynamics. RUNTIME: 48:14 EPISODE BREAKDOWN (2:28) “ I think it was within six months that we were able to have our first customer conversation.” (3:46) What can customers do with a runtime application protection platform? (9:38) “ What is interesting about our team is we don't come from prior security vendor companies.” (12:59) Ashley explains how her first “real job” at Google eventually led her to Operant AI. (15:51) “ I had many years of imposter syndrome to get over.” (17:57) Why working with design partner teams is key, particularly for stealth startups. (20:43) Priyanka discusses the company's early customer education efforts. (24:23) Ashley on why previous runtime application protection products hit “the trough of despair pretty fast.” (28:26) Turning design partners into paying customers was part of their seed-to-Series A transition. (31:04) Priyanka explains how Operant AI runs proof-of-concept programs for customers. (34:28) Why they decided to start up in stealth. (36:29) “ I honestly don't know how any consumer company could possibly start in stealth.” (38:35) “ We have the technical leadership in place now… to scale the product further.” (41:02) Inside their recruiting strategy and process. (44:35) What's changed since closing the Series A? LINKS Operant AI Dr. Priyanka Tembey co-founder, CTO Ashley Roof, co-founder, CMO Operant AI Secures $10M Series A to Protect the Modern Cloud Across APIs, Applications and AI SOC 2 compliance SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Startups are built on grit, vision, and — surprisingly — a lot of peer advice. In this episode, I sat down with Mallory Contois, Head of Community at Mercury and leader of Mercury Raise, their founder success platform. Drawing from their latest survey, Mallory shares eye-opening insights about how early-stage entrepreneurs navigate challenges like fundraising, hiring, and customer acquisition. Why do founders rely more on peer networks and podcasts like this one than their VCs for operational advice? Mallory explains the unique psychology that makes it hard for founders to admit uncertainty to their investors and why angel investors often provide more operational value than institutional funds. We also discuss key survey findings, including the evolving AI landscape, the benefits of accelerators, and how lean teams are reshaping what's possible in a startup.  Whether you're building your first company or gearing up for the next funding round, this episode offers actionable insights and a fresh take on founder dynamics in today's startup ecosystem. Subscribe now to Fund/Build/Scale and learn how to turn your idea into a sustainable business. RUNTIME: 44:44 EPISODE BREAKDOWN (2:19) A brief overview of Mercury and Mercury Raise. (3:42) Mallory describes a day in the life of Mercury's Community team. (6:18) Do mature startups worry about the same things as seed-stage teams? (8:41) “ We have a pretty good pulse on what people are talking about and what people are struggling with.” (9:26) Nearly a quarter of all survey respondents applied to accelerators but were rejected. (11:05) Why founders are more likely to get advice from this podcast than their VCs. (13:39) “ The peer connection that founders have is almost trauma bonding.” (15:02) “ We're seeing founders and investors giving the advice to be much more constrained in spend management.” (17:43) Mallory describes different founder archetypes who are attracted to Mercury Raise. (21:07) “ AI investments now are a lot more calculated than they were in the last couple of years.” (24:45) For AI founders, building in a hype cycle “ can be simultaneously demoralizing and exciting.” (27:17) How Mercury Raise creates value through community. (29:54) Mercury's Investor Connect program helps founders sharpen pitches. (32:54) “Fundraising in general is just a black box.” (36:13) Vibe check: “solo founders are actually becoming a little bit more common and a little bit more accepted.” (37:19)  ”Co-founder breakups — it's worse than the real thing.” (38:02) Mallory's advice for founders who are planning to fundraise in 2025. LINKS Mallory Contois Mercury Mercury Raise Mercury Investor Connect SUBSCRIBE

In October 2024, New York-based Swell VC announced its second fund with $11.5 million in commitments.  Co-founded by general partners Jay Patil and Rusty Ralston in 2011, the firm now manages two seed-stage funds and a special purpose vehicle with $19 million in assets. Compared to larger firms, they're small potatoes — but that's intentional. Swell VC is all about being hands-on: helping founders with critical early hires and go-to-market strategies. I invited them on Fund/Build/Scale to discuss their investment thesis, why diversity matters for building innovative teams, and how to know when it's finally time to stop thinking about your startup idea and start building. RUNTIME 42:09 EPISODE BREAKDOWN (1:36) Rusty explains how he and Jay met. (4:08) “ People determine the outcome of a company.” (5:36) “ You start the search when you're ready to hire. And then you build momentum.” (8:27) When Swell VC gets involved with founders, where they're looking to invest. (11:24) Jay talks about the firm's portfolio strategy and its second fund. (14:38) When it comes to early hiring, “ over the last 15 years, we've codified like all of our learnings.” (17:16) Where do  founders make the most mistakes in the hiring/interview process?  (21:43) “A  big blind spot is thinking diversity is just about hitting certain metrics.” (23:15) “ We're all about finding founders to live on what we call ‘the edge of the inside.'” (26:39) “ No solo founder can do everything forever.” (29:14) “ You don't need to build a full team right away. Your network is kind of your first line.” (31:55) Signals that indicate a founder's ready to take the leap into entrepreneurship. (34:40) Why Swell VC is looking for category-creating startups to invest in. (37:34) Questions Jay and Rusty expect founders to ask during the discovery meeting. (40:25) How they prefer to be pitched. LINKS Jay Patil Rusty Ralston Swell VC info@swell.vc Swell VC Closes $11.5M Fund II, Proving Small Funds Can Deliver Big Wins (PR Newswire) Distributed to Paid-In Capital (DPI) definition SUBSCRIBE

If a team hasn't built a minimum viable product, secured paying customers, or demonstrated strong unit economics, what exactly are seed-stage investors betting on? To get some answers, I sat down with Nnamdi Iregbulem, a partner at Lightspeed Venture Partners, to discuss what drives seed valuations, the traits of successful founders, and his perspective on AI startups. “A lot of the pitches that I get are basically two people, a PowerPoint deck, and their dog,” Nnamdi told me during our conversation in October 2024. Nnamdi shared his journey from coding as a kid to investment banking at JP Morgan, growth-stage investing at Iconiq Capital, and now helping early-stage founders at Lightspeed. He explains why seed valuations often reflect the opportunity cost of the founding team more than traditional factors like interest rates or public market comps, and highlights the rising costs of GPUs and AI talent as critical considerations. We also explored the traits that set exceptional founders apart — like strong domain expertise, adaptability, and demonstrated excellence — and why inference-based AI startups may have an edge over those focused on training new models. For aspiring VCs, Nnamdi offers practical advice on developing domain expertise, building a network, and honing the skills needed to evaluate companies effectively. Whether you're a founder, investor, or simply curious about the startup ecosystem, this episode is packed with actionable insights.   RUNTIME 33:24 EPISODE BREAKDOWN (2:24) “ I was the first-born son of two Nigerian immigrants who really badly wanted me to be a doctor.” (6:17) “ I was sort of like, ‘what do I know about early-stage companies?' I never worked in a startup.” (8:50) The day-to-day work Nnamdi does with the founders in Lightspeed's portfolio. (11:13) He explains why seed valuations aren't valuations. (13:31) “ The only characteristic… that had any real predictive value was the opportunity cost of the founder.” (16:43) “ Coming from a large and stable big tech company is not the positive signal that it used to be.” (17:32) The weights and measures he uses to assess seed-stage founders. (19:33) When domain expertise is (and is not) useful. (20:53) How he evaluates technical vs. non-technical founders. (24:16) “A lot of the pitches that I get are basically two people, a PowerPoint deck, and their dog.” (25:18) How to pitch Nnamdi directly. (26:21) Setting valuations is “ more driven by the founders than it is by us.” (29:33) His advice for anyone who wants to break into venture capital. LINKS Nnamdi Iregbulem Seed Valuations Aren't Valuations, whoisnnamdi.com email Nnamdi Lightspeed Venture Partners SUBSCRIBE

In the startups I worked at, we never had spare laptops.  When we hired someone, we'd order their laptop that day. That's Startup Cashflow 101: don't spend money until you have to. The same principle applies to your leadership team. Hiring a CMO before product-market fit? Too soon.  And a CEO can handle COO duties for a while. Most seed-stage companies don't need a full-time CFO either.  A good controller can handle day-to-day finances, while a fractional CFO can plan future fundraising and create investor-friendly forecasts — all without reducing your runway. To understand why a fractional CFO might be the smarter move, I spoke to Dan DeGolier, founder of Ascent CFO Solutions. Runtime 27:21 Episode Breakdown (1:44) Dan explains Ascent CFO Solution's origin story. (4:53) Why so many founders hire full-time CFOs before they actually need to. (6:33) A list of specific value-adds a fractional CFO can provide. (7:29) “We might be two days a week or three days a week. But we are very much a part of that team.” (8:57) Inside Dan's client onboarding process. (12:44) “Part of it is getting a handle on cash flow and spend.” (15:24) “Understanding what the risk factors are to your runway is really critical.” (18:39) Which stats and KPIs are most important to share with the entire company? (20:51) If you want cash flow to break even, “be capital efficient to begin with.” (23:31) Clients “often supplement a VC round with a venture debt round so they can extend that runway a little bit further.” (25:09) How to interview a CFO if you don't have an entrepreneurial background. (26:08) Resources Dan recommends for founders seeking financial discipline. Links Dan DeGolier Ascent CFO Solutions Good to Great: Why Some Companies Make the Leap...And Others Don't, Jim Collins Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant, W. Chan Kim and Renee Mauborgne Traction: Get a Grip on Your Business, Gino Wickman EOS One® Subscribe

When I learned that MaC Venture Capital just raised $150 million for its third fund since 2020, I immediately reached out for an interview with Marlon Nichols, the firm's co-founder and managing general partner. Marlon previously co-founded Cross Culture Ventures, which merged with M Ventures in 2019 to form MaC VC. In this interview, we talked about his path from enterprise software into venture capital, the concept of cultural investing, and MaC VC's focus on diverse founders. He also explained what types of startups the new fund is open to and discussed some of the criteria he uses to assess the strengths of founding teams (and their ideas). Runtime: 45:44 Links Marlon Nichols Contact Marlon MaC Venture Capital Exclusive: MaC VC raises $150 million for its third fund in four years (Fortune) The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, Ben Horowitz Secrets of Sand Hill Road: Venture Capital and How to Get It, Scott Kupor Subscribe

In this episode of Fund/Build/Scale, host Walter Thompson interviews Sahil Agarwal, CEO and co-founder of Encrypt AI. Sahil shares his journey from academia to leading an international AI company, discussing the importance of storytelling, confidence, and addressing biases within AI models. He also delves into challenges faced by immigrant entrepreneurs and the balance between leadership and employee well-being. Sahil provides insights into navigating enterprise AI security, fundraising strategies, and the intrinsic demands of running a startup. Tune in to uncover strategies for launching a company and overcoming industry hurdles. Runtime: 33:04 (1:46) Sahil describes Enkrypt AI use cases that “ensure equitable and safe use of AI for everyone.” (3:36) How his background in applied mathematics led to a career in enterprise security. (6:45) “You work until two in the morning whether that's PhD or a startup, and you wake up and you start again.” (8:34) “It took us some time talking to prospects and talking to people in the space to really hone in on the problem.” (11:42) Sahil's path to obtaining the green card that would let him launch his own company. (15:31) “There has to be some sort of confidence that we have to project in front of investors and in front of enterprises or prospects.” (17:19) “You're accountable to everyone else in your company. That's my principle of leadership.” (20:26) How Sahil and co-founder Prashanth Harshangi approach work-life balance. (24:27) Setting expectations with investors and leading Enkrypt AI's GTM strategy. (29:18) His advice for anyone pitching a seed-stage AI startup: “don't pitch a technology, pitch a story.” (31:17) The one question Sahil would ask an early-stage CEO if he were interviewing for a job. LINKS Enkrypt AI Sahil Agarwal, co-founder and CEO Prashanth Harshangi Enkrypt AI Raises $2.35 Million To Take On The Chatbots Going Rogue SUBSCRIBE LinkedIn Substack Thanks for listening! – Walter.

Branding is a condensed form of storytelling. That's my opinion, but it's also shared by David Placek, founder and president of Lexicon Branding. Here are a few of the companies and products they've named since 1982: Subaru Outback, Subaru Forester BlackBerry Pentium PowerBook Nissan Rogue Lucid Azure Sonos Swiffer NVIDIA Shield Febreze In May 2024, I interviewed him at his headquarters in Sausalito, California about brand architecture and positioning, the merits of being bold and authentic, and the methodology his company uses to transform innovative ideas into distinctive names that resonate.  Our conversation focused on aligning brand with market behavior, the art (and science) behind selecting a name, tools and exercises for brand identity creation, and techniques for validating a brand name before you commit to it. He also offered suggestions for early-stage teams on tight budgets and shared some insights from a study on branding for AI startups: “Don't overpromise, don't overhype, don't participate in all this hype.” RUNTIME 44:10 EPISODE BREAKDOWN (2:56) ”We have a process that takes that new idea and, and along the way, the goal is to give it a voice, a distinctive voice.” (4:02) How Lexicon Branding develops “coined” brand names. (7:18) Over time, David realized the company needed a creative layer and an engineering layer. (8:31) “Right now, in-house, we have at least three programs that are AI-based.” (10:22) “We are first and foremost a creative consulting firm, so everything has to be customized.” (12:09) David ballparks cost, timelines, and explains how Lexicon Branding works with clients. (15:07) “We create a vessel that will carry the story into the marketplace.” (17:36) How to validate your branding idea before fully committing to it. (21:53) Using generative AI in client work “is not only saving us time, but it's getting more information.” (25:07) Situations where David recommends changing your company's name. (27:39) Head of Research Dmitri Seredenko offers an overview of an AI startup branding survey. (29:12) The challenge of injecting genuine emotion into your brand. (33:02) “I don't think any brands have really taken a stake on what they really want to be known for.” (35:56) “Don't overpromise, don't overhype.” (38:53) Why adding “AI” to your brand is a bad idea. (41:36) After you've made a decision, “stop trying to be comfortable about the new name.” (42:45) David describes the emotional experience of encountering his brands in daily life. LINKS Lexicon Branding David Placek Dmitri Seredenko 6 Things You Need to Know if You're Building an AI brand SUBSCRIBE

Deeptech founders are solving problems that most of us don't think of as problems and tackling challenges that push the boundaries of what we think is possible. This interview with Justin Fiaschetti, CEO and co-founder of Inversion, is a good example. Inversion is building a platform that will enable space-based cargo delivery using autonomous re-entry vehicles with parachutes that will let them deliver goods from space to pretty much anywhere on Earth in less than 60 minutes within 20 feet of their customer. After my initial chat with Justin to prepare for this interview, I literally had to take a walk to process it all. Today, Inversion is announcing its $44 million Series A round — a clear signal that investors and potential customers believe the company is on the verge of something groundbreaking. “None of our customers care about how technically cool or what new fun technology we have on our product,” said Justin. “All they care about is can they get their cargo in under an hour, wherever they want. And so our goal is to do the minimum amount of technical innovation in order to meet our customers' needs while having a growth path to continue to increase the capability [and] reduce the cost for our customers.” I interviewed him about early customer discovery and market validation, how Inversion is developing its go-to-market strategy, and asked how he plans to put the Series A to work in the company's next stage of development. We also discussed the unique challenge of pitching something to investors that only exists in your imagination. “What is the addressable market for delivery from space? It doesn't exist right now,” said Justin. “Fundamentally, we're making a new market.” RUNTIME: 56:15 EPISODE BREAKDOWN (3:55) “Space really only has two viable business models. And we asked ourselves, ‘what's the third thing that's going to happen?'” (6:05) How Inversion's on-demand space cargo delivery platform will work. (8:12) “I like to define ourselves by our customers rather than by our technology.” (12:08) “Having closed this Series A, there are a couple of big things for us.” (14:33) Differences between the Ray reentry vehicle and Arc, the larger prototype. (16:50) Inside Inversion's go-to-market strategy. (20:39) “Nobody's built this before. There is no playbook. There is no rule set that you have to follow.” (25:21) Justin's approach to validating customer demand for space-based cargo delivery. (27:40) “Our first investor pitch went terribly.” (31:07) Why Justin and Austin pivoted away from their initial idea. (34:40) “There is a huge market for on-demand and rapid cargo delivery.” (39:18) “We are the first new space company to develop parachutes in space.” (43:56) His framework for staying focused on product and customer needs. (46:00) “Starting with the military has been critical for us.” (50:45) “One of my personal goals is to deliver the Olympic torch.” (51:13) How Inversion is navigating the Valley of Death. (54:26) One question he'd have to ask the CEO if he were interviewing for a job at a deep tech startup. LINKS Inversion Justin Fiaschetti, CEO/co-founder Austin Briggs, CTO/co-founder Inversion Space accelerates orbital reentry vehicle tech with $71M Space Force contract (TechCrunch) Inversion secures reentry license for first mission (Space News) Jobs at Inversion SUBSCRIBE

If you want a healthy relationship, it's essential to set clear expectations and boundaries from the start.  The same holds true for a founder and their board. Despite the power dynamics, CEOs can still create a transparent communication framework that respects everyone's limited time. In part two of my interview with TigerEye co-founder and CEO Tracy Young, we discuss her approach to work-life balance, the unique challenges women founders face while fundraising, how to run a board meeting in 60 minutes, and the importance of gaming out worst-case scenarios. Runtime: 24:58 EPISODE BREAKDOWN (2:20) Why traditional 80-page board decks are “just not helpful for strategic discussion.” (5:32) How Tracy structures memos for board meetings. (7:18) The importance of gaming out worst-case scenarios with your team. (9:31) “Our motto is: ‘go towards where it hurts.' Go fix it.” (12:40) Tracy and (co-founder/husband) Ralph's approach to work-life balance. (15:26) “It's trite to say, but I try to meditate when I can.” (17:11) “I have met a lot of women founders who have told me horrific stories.” (20:24) “You look at who's writing the checks and are actually decision makers. They lean more towards male — actually white males.” (22:59) “You shouldn't be talking to customers in one meeting and in the same day meeting investors.” (23:48) The one question she'd have to ask a CEO if she were interviewing for a startup job. LINKS Tracy YoungWhy I started TigerEye Early-stage board decks are dead: How to run a meeting in 60 minutes TigerEye Ralph Gootee SUBSCRIBE

In 2011, Tracy Young co-founded PlanGrid, which made software for construction teams. After scaling the company to 450 people and raising $69 million, it was acquired by Autodesk in 2018 for $875 million. That's a win, but Tracy and her partners didn't go for the exit because they'd reached the peak of the mountain. They cut the deal because PlanGrid was behind in the market, and they didn't know how to catch up. Three years later, during the pandemic, Tracy and her husband, Ralph Gootee, co-founded TigerEye, a RevOps AI agent that lets analysts answer questions and allocate resources based on data that's updated multiple times each hour.  Last year, TigerEye closed a $30 million Series A. She describes it as “moneyball for business,” the tool she wished she'd had at PlanGrid when she was fighting entrenched competitors who were just better at enterprise sales.  In part one of our interview, she explains why they started their new company up in stealth and how TigerEye reflects her vision of what enterprise software should accomplish. She also shared what she'd learned as a CEO her second time around about building early teams and managing a hybrid workplace. Subscribe now to get part 2: Her approach to work-life balance The unique challenges women founders face while fundraising How to run a board meeting in 60 minutes, and The importance of gaming out worst-case scenarios. Runtime: 23:09 EPISODE BREAKDOWN (2:53) TigerEye's origin story: “We wanted a second chance, and that became a big desire of ours.” (5:11) “There's certain decisions that only leadership and the CEO can make.” (7:58) “We just really sucked at selling to the enterprise.” (9:53) How to manage customer discovery while you're in stealth. (15:53) Tracy's tactics for managing a remote-first team effectively. (19:25) When it comes to personnel, it's “much harder to be mediocre at a small startup.” (21:21) Why she still interviews every new hire at TigerEye. LINKS Tracy Young Why I started TigerEye 5 failure points between 5 and 100M ARR  TigerEye Ralph Gootee SUBSCRIBE

Most of the world's talent goes untapped. Unrecognized. With that in mind, I interviewed Laura González-Estéfani, founder of Miami-based VC firm TheVentureCity in May 2024. We talked about the potential of global talent and why more investors need to broaden their scope beyond major tech hubs. This episode provides valuable insights for founders who don't have large networks or a business background. She offered practical advice on navigating the VC approval process, building trust with investors, and avoiding common pitfalls such as overdilution of equity. She also talked about what she's looking for, and how she prefers to be pitched. Runtime: 45:01 LINKS Laura González-Estéfani TheVentureCity Growth Scanner AHA (beta) TheVentureCity jobs board SUBSCRIBE

Today is my 55th birthday! I was planning to take the day off, but I started thinking about a few people my age who work in tech and have been recently laid off. Unlike workers in their 20s and 30s, they're facing a very different set of pressures: family, college payments, aging parents, retirement, etc. Most of the ones I know are having a hard time landing interviews, let alone full-time jobs. This is the shortest episode I've ever released, so technically, I guess that makes this a hot take. I generally avoid those, but it's my birthday and I'm feeling self-indulgent.