Technori Podcast with Scott Kitun

Scott's back with golf betting consigliere Joe Koziol to preview the 2025 US Open at Oakmont, the hardest test in golf—and the most honest major to bet. The guys break down who can survive the brick-wall greens, brutal rough, and USGA sadism, then roll through their top plays, longshots, and the unofficial return of their flagship segment: Guy Stuff. What You'll Learn: Why Oakmont rewards discipline, not dopamine Scott's favorite Top 10 prop that's free money (he swears) Joe's sleeper pick who's either missing the cut or finishing T-3 The one LIV player neither of them will touch Why betting the cut line might be more fun than betting the winner Follow Scott on IG/Twitter @kitun

Scott's back with his golf wagering pal Joe Koziol to break down this week's PGA Championship and whether or not Quail Hollow is just "Rory McIlroy Country Club". The two discuss a few emerging storylines such as; will Jordan Spieth sneak into the elite Grand Slam club? Who has the tastiest odds coming into the weekend, and whether or not the PGA made the right call moving its championship to May.

This week, something seismic happened in private markets. Jeff Bezos, Michael Dell, and Coatue's Philippe Laffont announced a $1B tech fund that's now accessible to individual investors — with minimums starting at just $50K. Let that sink in. The floodgates are opening. What used to require millions and insider access is now coming to retail. First Hamilton Lane launched the first truly retail private fund exclusively on Repubic with a $500 minimum and now Coatue offering access to its own unique offering at $50k (funds like these typically have minimums in the millions). In this episode, Scott is joined by KingsCrowd's Head of Product, Brian Belley, to unpack the real impact of this new "public-private" trend — and how everyday investors (and fintech bros) can take advantage of this radically evolving market. What they discussed: - Why this marks the official arrival of the retail private equity era - The pros, cons, and potential traps for new investors - How to build a modern portfolio without getting wrecked by fees, hype, or fine print - Why the next generation of private investing will blur the lines between public and private assets Support the show (and your wallet) by creating a free account at Kingscrowd.com. Follow Brian @ Linkedin.com/in/brianbelley Follow Scott on IG/Twitter @Kitun

Scott sits down with venture capitalist, essayist, and Slow Ventures GP Sam Lessin for a candid, high-signal conversation about the state of venture capital—and why the old playbook is officially dead. Sam unpacks the ideas behind his viral VC25 manifesto, including why the startup conveyor belt model is broken, how today's founders are flying blind, and what it really takes to build something worth betting on in a post-factory era. Together, Scott and Sam dive deep into the evolving role of seed investors, the myth of the “10x engineer,” and why most unicorns are now zombified corpses soaking up capital and talent. They riff on founder delusion, LP dysfunction, the commoditization of software, and how a new generation of operators must be built for long-term reality—not short-term hype. It's a provocative, honest, and sometimes brutal look at how we fund, build, and believe in companies today—and why SFD (Straight F*cking Down) might be the new north star for modern venture. What You'll Learn: -- Why the “VC Factory” model is gone for good -- How to survive as a seed fund in the mega-fund era -- Why great companies must now be built for forever, not acquisition -- What matters more than tech: story, founder, deal Support the show (and your wallet) by creating a free account at Kingscrowd.com Follow Sam Lessin on Twitter @lessin Follow Scott on IG/Twitter @Kitun

Scott sits down with longtime friend, journalist, and cultural critic John McDermott for a no-holds-barred conversation on the rise of the grift economy. John and Scott re-trace the evolution of modern hustle culture to unpack the cult of tech founders, the blurred lines between personal branding and deception, and why irrational self-confidence is both a feature and a bug of startup life. Along the way, the duo riff on everything from J.R. Smith's delusional greatness to Mark Zuckerberg's masculinity arc, fake wellness routines, and the eerie emergence of AI-driven misinformation. John shares what it was like to go toe-to-toe with Jay Shetty, the media's retreat from accountability, and how we're all becoming lone agents in a broken information ecosystem. It's a sharp, funny, and sobering look at an era where everything is a grift—and everyone's a brand. What You'll Learn: -- Why the “rise and grind” founder archetype is built on delusion -- How fake personas thrive in a media landscape with no referees -- Why we're only at the beginning of the grift era—and how AI will amplify it -- What snake oil salesmen of the 1900s can teach us about today's digital hucksters Support the show (and your wallet) by creating a free account at Kingscrowd.com Follow John McDermott on Twitter @McDermott Follow Scott on IG/Twitter @Kitun

In this episode, Scott sits down with legendary host and comedic trailblazer Craig Kilborn for a wide-ranging conversation on life after late night, creative independence, and what it really means to stay above the fray. From his iconic runs at ESPN, The Daily Show, and The Late Late Show, Craig reflects on the highs of fame, why he walked away, and how he found peace (and punchlines) off-camera. Scott and Craig share their philosophies on aging gracefully, drinking in moderation, and never chasing the night. They riff on Frasier, Scotch, the Reuben sandwich, and their favorite rewatchable movies—from Predator to North by Northwest. Plus, Craig shares what he's up to now with his podcast The Life Gorgeous, his love for California road trips, and why leadership and attitude matter more than ever. Lessons Learned: - Why Craig Kilborn left late night at the top—and doesn't regret it. - How to craft a creative life without burnout or bitterness. - Why being genuinely happy is a competitive advantage. - What makes a sandwich truly great. Support the show by signing up for a free account at KingsCrowd.com Subscribe to Craig's podcast: The Life Gorgeous Follow Craig on Instagram: @mrcraigkilborn Follow Scott: @kitun

A different tradition unlike any other... Gambling on golf. Welcome to Scott Show: Masters Week Edition. Scott is joined by local legend and friend Joe Koziol to dive deep into one of the year's most beautiful, chaotic, and bank-breaking sports weekends, The Masters

In this episode, Scott sits down with journalist-turned-operator Eric Newcomer for a wide-ranging conversation about building in public, the evolution of venture capital, and what it's really like to run a media business. Eric shares the backstory of launching Newcomer, from a solo Substack to a $2M+ revenue business with marquee events like Cerebral Valley. The two reflect on the blurred lines between media and entrepreneurship, how trust and access shape great reporting, and the surprisingly human side of building a company. Then, Scott and Eric dive deep into the state of venture capital: the private-equity-ification of mega-funds, the uncertain future for emerging managers, and why it's getting harder to find the next generation of category-defining companies. Eric offers sharp takes on AI, fundraising hype, and what LPs really want. It's a thoughtful, honest, and often funny look at what happens when a journalist steps behind the curtain and becomes a founder himself. What You'll Learn: - Why Newcomer leaned into events—and how it became a real business. - The unspoken truth about founder glorification (and how hard building really is). - How venture capital is shifting—and why SaaS may have spoiled the party. - What separates good journalism from performative puff pieces. - What it feels like to lead a small team and be responsible for real livelihoods. Bonus: Invest with your eyes not your ears. Markets tank following Trump tariffs. Support the show by signing up for a free account @ Kingscrowd.com Subscribe to Eric's newsletter and podcast: Newcomer.co Follow Eric: @ericnewcomer Follow Scott: @kitun

In this episode, Scott sits down with Darren Marble — the creator of Going Public and founder of Issuance — for a wide-ranging conversation on the rise of retail investors, the evolution of equity crowdfunding, and why he believes the best days of this industry are still ahead. Darren shares the inside story of launching Going Public, a groundbreaking series now partnered with X (formerly Twitter), where everyday people can invest in startups while watching. He opens up about the challenges of getting mainstream media to understand the vision, the value of showmanship in a complex industry, and how they're landing major talent like Baron Davis, Floyd Mayweather, and Steve Aoki to bring visibility to private investing. Scott and Darren go deep into the early days of crowdfunding, the Elio Motors deal that kicked it all off, the philosophy behind Issuance's white-label platform, and why building a frictionless checkout for investing (complete with Apple Pay and USDC) was always the obvious play. This episode is full of gems on what it really takes to build trust, media attention, and infrastructure in a space often ignored by institutions — until now. Support the show by signing up for a free account @ Kingscrowd.com Learn more about Darren's work @ goingpublic.com, issuance.com Follow Darren: @darrenmarble Follow Scott: @kitun

In the inaugural episode of The Scott Show, host Scott Kitun welcomes his good friend and Founder of Republic, Kendrick Nguyen, to break some BIG news and to discuss the game-changing shift towards retail happening across private markets. Key Takeaways: → Republic's Major Announcement – A new partnership with Hamilton Lane, bringing institutional-grade private equity to retail investors via blockchain tokenization. → The Power of Private Equity – Unlike volatile public markets, private equity has outperformed 19 of the last 20 years. Retail investors now have access to previously exclusive assets. → Why Tokenization Matters – It enables greater accessibility, easier tracking, and future liquidity, potentially allowing private investments to trade more like public stocks. → Republic's Vision – To become the go-to platform for investing in private assets that power the world—whether infrastructure, AI, sports ownership, or alternative funds. → Scott and Kendrick dive into how the financial landscape is evolving, why retail investors have been historically locked out of high-performing assets, and what the future holds for tokenized investments and online private markets.

In this episode of the Technori podcast, host Scott Kitun interviews Jeff Annison, the co-founder and president of Legion M. They discuss Annison's journey from mechanical engineering to entrepreneurship, highlighting his experiences in various startups, including a streaming mobile television venture and a music-related startup. Annison shares insights into his career transitions, the challenges he faced, and the evolution of his ventures.Key Highlights:Quibi chat: despite failures, a quick look at its innovative content creation and distribution model. (5:52)Legion M proposition as a fan-owned movie studio. (9:09)Hollywood strikes and the future of entertainment. (15:11)Hollywood's shift to streaming and Legion M's fan-owned model. (24:12)Using fan funding for Hollywood movies. (28:09)Investing in fan-funded content. (37:59)

Scott Kitun sits down with acclaimed journalist and author Taylor Lorenz to set the record straight regarding internet history, the premise of her book, "Extremely Online," (available now). She discusses the evolving landscape of the tech world, the importance of strong social safety nets, the impact of AI on content creation, and Lorenz's thoughts on various social platforms. Key Highlights:The impact of social media on fame and celebrity. (2:51)The fundamental issues creators face including the challenges of accessing healthcare and unions' potential role (and over-reliance) in addressing these concerns. (3:12)The evolution of influencer culture and the impact of social media platforms. (7:50)Creator unions and collective bargaining in the digital media industry. (15:19)The discussion shifts to the influence of AI, with Scott highlighting how it might disrupt the middle class and alter traditional career paths. (20:41)Taylor provides a balanced view on AI's potential, noting that while there are concerns, AI also offers various creative tools. She also mentions using ChatGPT and its current limitations are not scary. (22:18)Scott dives into the human element in content creation, emphasizing that human-driven competition and creativity remain irreplaceable. (24:14)The conversation concludes with Lorenz's thoughts on the best platforms to follow her work,  her move away from Twitter (X) for tech commentary. (27:54)

Scott Kitun talks to StartEngine co-founder Howard Marks. The conversation starts with Kitun's curiosity about Marks' early involvement in crowdfunding, despite having been an entrepreneur (founder of Activision) for a long time. Marks recounts his journey from investing in entrepreneurs in Los Angeles to eventually building StartEngine. He reflects on entrepreneurs' difficulties when raising capital, especially those who don't fit the traditional "Stanford-educated, white male" profile. Marks shares his experience with the initial skepticism and resistance faced, emphasizing the potential opportunity when the general consensus is against a new idea. He also highlights the success of StartEngine so far, its future prospects, and the company's recent launch of a secondary marketplace for trading alternative assets.Highlights include:Howard Marks reflects on his entrepreneurial journey, the origin of StartEngine, and the difficulty entrepreneurs face in raising follow-on investments, particularly those from diverse backgrounds (1:58).Marks expresses his frustration with the traditional investment model and discusses how the Jobs Act of 2012 sparked his interest in crowdfunding as a potentially revolutionary opportunity (12:39).Marks discusses the growth and success of StartEngine, the launch of its marketplace for trading, and the future prospects of the platform (14:02).

Scott Lynn, founder and CEO of Masterworks, joins Scott Kitun on the show. As a long time art collector and enthusiast, Lynn saw a massive space in the market for fine art - which includes many pieces that are valued in the millions of dollars - to be invested in fractionally but art lovers and investors worldwide. In this episode, Scott Lynn shares his foray into entrepreneurship, developing the Masterworks platform and the promise of the art + internet to make incredible opportunities. The two Scotts digs into the markets, expressing confidence the markets will swing back for alts. Lynn also  dives into the Masterworks platform and how to think about artwork as a part of a diverse portfolio and how to build your own portfolio. Check out Masterworks here.  

Bored Elon Musk, a pseudonymous influencer, joins Scott Kitun on the pod. Bored has built his following over most of the past decade on Twitter. What started out as a joke account gradually - alongside the growing notoriety of Elon Musk - into an influencer account with over a million followers. Bored shares how he built his following and monetized his account, including his Bored Box. Scott and Bored talk about the idea of playing a character as a business, performing in good faith and best use cases for crypto and NFTs. Bored also talks about distancing his brand separate from Elon and shares a few thoughts on the latest Twitter company news. 

Harper Reed, founder and CEO of Galactic, joins the show with Scott Kitun. Reed, the former Head of Commerce at Braintree and President Obama's CTO during his re-election campaign, is a longtime tech entrepreneur (and Technori supporter) working to make technology work better for everyone. Like many founders experienced early on in the pandemic, Reed had to make a major pivot. He shares his latest entrepreneurial journey moving Galactic from health/medtech-centered company into one focused on building fintech products native to Web3. Scott and Harper dig into the utter lack of accessibility for regular people to use crypto in their everyday lives, and how to build products with the user in mind. Reed  makes an actionable use case for Bitcoin, and ways of thinking about crypto and blockchain in a way that touch people's lives. They also touch on their Chicago roots, finding funding amidst the pandemic for veteran and rookie entrepreneurs. 

Milan Kordestani, founder and CEO of Audo, joins the show with Scott Kitun. Audo is a career building platform that combines e-learning and job opportunities that fit the skills you learn. Scott and Milan dig into the changes coming to education, the value of college and avoiding debt. They also touch on just how gamification could and should play into the ways we learn, and building curriculum around engagement. Milan dives into his own college experience and not finding value in curriculum options given to him in college, which ultimately was the first kernel of his idea for Audo. 

Lorel Scott, co-founder and COO of StartupStarter, joins the show with Scott Kitun. StartupStarter is launching the first ever in-person Equity Crowdfunding Week (ECW), a showcase and awards show for equity crowdfunding startups and investors to come together for a 3 day celebration of a growing crowdfunding community. Lorel shares  how he and his co-founder came up with  StartupStarter in the height of the pandemic and have been working the past two years to put together a showcase that shines a bright light on the equity crowdfunding sector. They talk about the faults of the industry, how to grow awareness for crowdfunding and why the lack of volatility in private markets is such a heavy factor. They also dive into ECW (which Scott will be keynoting the awards show), the focus on music and inclusivity and special events happening in LA from 11/9-11/11. You can register here for the conference. 

Brittany Davis and Christie Pitts, general partners at Backstage Capital, join the show with Scott Kitun. Brittany and Christie talk about the present day investing landscape and why the future of VC will trend towards inclusiveness (or lose). The group shares their thoughts and experiences with the top VC firms, why so many are resistant to change and where the next generation of founders and investors is primed to shape who and what gets funded differently from their predecessors. We also talk about Backstage's new Flex Fund II, which KingsCrowd (Technori's parent company) will provide data and ratings on promising online deals that have underrepresented founders. You can learn more here.

Mike Mercier, founder and CEO of VonMercier, joins the show with Scott Kitun. They talk about how changing what we can do with vehicles, starting with the idea of VonMercier's electric hovercraft Arosa. Mike dives into his 10-year founding journey with late nights and weekends dedicated to coming up with the concept, finding the right materials and creating something from just an idea to a full-fledged company. Scott and Mike also dig into the building a business model for small-scale vs mass market. VonMercier is currently raising a CF round on Republic. 

Justin Miller, founder and CEO of Showplace, joins the show with Scott Kitun. Showplace aims to be a one-stop shop for people looking to rent out their properties with the supplies, design, furnishings and everything else you need to set up a short-term rental. Justin shares the company's hefty aim to be the modern infrastructure for short-term rentals, and filling a space opened up by the past decade's surge of companies like AirBnB and VRBO. As a three-time founder, Justin also dives into his decades long journey as an entrepreneur, including his first company  Notehall which was the first company on Shark Tank to receive an offer from the Sharks. Scott and Justin talk about becoming repeat founders, working with longtime colleagues and capitalizing on the startup mindset. For any founders listening to this, it's a must listen for turning ideas into businesses and how to move your company forward. 

Ashik Ahmed, co-founder and CEO of Deputy, joins the show with Scott Kitun. Deputy is a company focused around simplifying work life for the shift worker. As an employee management platform, Deputy specializes in timesheets, scheduling, tasks and workplace communication. Ashik shares the founding story starting with his own childhood growing up around shift workers in the family to working on the initial concept  with his cofounder who ran an aviation ground handling business at the time. Seeing how many people airlines didn't employ themselves, but were in fact shift workers, sparked the idea of creating a platform that better serves the tens of millions of gig workers across the globe. Scott and Ashik dissect the concept of the gig economy, its pros and cons, and how to empower shift workers besides lip service. 

Rory Rubin, co-founder and CEO of S.I. Container Builds, joins Scott Kitun on the show. S.I. Container Builds offer customizable ADUs (accessory dwelling units) using shipping containers that are affordable, simple and environmentally conscious. Rory shares with Scott the origin story for starting S.I. Container Builds. According to Rory, there are more than 23 million shipping containers that can be recycled as potential ADUs that are low-cost to build and be built quickly. Rory talks mission to address the housing crisis, why this opportunity left her switching careers and entering the construction space she grew up around with her family. They share stories about the various use-cases for ADUs, getting seed investment from Hyde Park Angels (and from previous guest Pete Wilkins) and starting a company from scratch.   

John Wu, CEO of Gryphon, joins the pod with Scott Kitun. Gryphon is a wireless router built around online safety, privacy and protecting the central point of your digital life at home. John first starting thinking about the idea for the router after watching his young daughter access the internet and come across NSFW (or children) content. Scott and John catch up about the essential role of data in our lives, why we should care where it goes and treating children's digital lives with equivalent protections and safeguards we use in the physical world. John also shares new features coming to Gryphon including password manager functionalities, VPN and other privacy protections using  blockchain technology that transfer control away from third parties and into the hands of the user.  Gryphon is currently raising a CF round on Republic. 

Cody Barbo, founder and CEO of Trust & Will, comes back on the show with Scott Kitun.  Cody catches up with Scott after three years of growing the Trust & Will business  from a seed round CF raise on Republic to a $15 million Series B and recent venture round led by UBS. They talk about the journey Trust & Will has been on, how Cody first got the idea after trying to work through finances with his wife and identifying a very clear need for simple, easy to set up estate plans and wills. Scott and Cody lament on the state of fundraising and its challenges. They dig into the different type of rounds Trust & Will has endured, the highs and lows of their equity crowdfunding campaign, why venture is still best suited for later rounds and touching on the evolving mindset of the retail investor. 

Alex Giannikoulis, founder of Ivee, joins the show with Scott Kitun. Ivee is a "mobility as a service (MaaS)" platform that adds a suite of apps and experiences that elevate your time as a passenger in commute. The Ivee dashboard connects your phone to a 10" tablet in the backseat to access services like Netflix, Spotify, Calm as well as physical experiences like surround sound and in-chair massage functionality. Alex and Scott go into the state of the auto industry, improving the in-car experience and why Tesla  - despite its flaws - raised the bar by changing customer expectations. Ivee is currently raising on a CF round on Republic. 

Vijay Kedar, co-founder and CEO of Tomorrow Health, joins Scott Kitun on the show. Tomorrow Health is a health tech company that aims to restore at-home care as the primary & preferred destination for patients of all ages. Vijay dives into how Tomorrow Health streamlines healthcare processes and at-home service to enable patients to go home and spend less time at the hospital. He shares his founding story of taking time off from his job at Oscar Health to help his mom through her cancer treatments and noticing all the deficiencies from insurance to  point of care. Scott and Vijay also talk about the problems of health care, how patients fall through the cracks, and creating businesses that serve providers, patients and companies equally well. 

Ana Mahony, founder and CEO of Addition Wealth, joins the show with Scott Kitun. Addition Wealth is a fintech platform that offers a suite of tools, resources and financial advisors to help employees make better financial decisions. Ana shares how she decided to jump into entrepreneurship after struggling to help her mom figure out her finances and the complications she faced. Scott and Ana  go back and forth over the lack of financial literacy employees have with their own contracts, how to understand their equity compensation and why that understanding doesn't exist across the wealth gap. They also talk about the inherent risks of joining a startup and why early employees carry the of that  risk burden. They touch on Addition's B2B2C business model, how to offer personalized financial advice at scale and why learning about your money early makes many decisions down the road that much easier.  

Nathan Beckord, founder and CEO of Foundersuite, joins the show with Scott Kitun. Foundersuite offers a suite of software tools, templates and education to help founders and CEOs execute more efficiently. Nathan comes back on the pod to talk about the Foundersuite journey, lessons he's learned from working with thousands of founders and learning strategies to successfully get early stage projects off the ground. Scott and Nathan share investor stories, teaching founders the volume game when it comes to getting investments and why it's critical for founders up to Series A to lead the charge on fundraising rounds. 

Galiano Tiramani, CEO and founder of Boxabl, joins the show with Scott Kitun. Boxabl makes ADUs (accessory dwelling units) that  can ship anywhere as a giant box that unfolds onto your plot of land. Galiano dives into his entrepreneurial journey with startups in the trendy spaces such as Bitcoin and cannabis, as well as his years long pursuit of getting Boxabl up and running. Scott and Galiano talk about the the logistics behind mass production and Galiano's plan to get several manufacturing warehouses - essentially auto plants but houses - to meet demand and ship Boxabls around the country. Besides being famous for Elon Musk's rumor of living in a Boxabl, they are also taking investments on Start Engine with over $12 million raised to date. Disclaimer: Anyone can buy shares in Boxabl for $0.80 at invest.boxabl.com and read the offering circular contract at boxabl.com/circular

Hadley Harris, cofounder of Eniac Ventures, joins the show with Scott Kitun. Hadley humors Scott on one of his favorite topics - dealing with venture capitalists. Scott and Hadley dig into the rise of VC competition and why VCs can't afford to be as dismissive or authoritative in the new environment with a growing list of funding options for founders. They also talk about the power of Twitter in the start up world, VC trends, ideal companies and finding the right fit between founders and the problem they set out to solve. 

Nick deWilde, co-founder of Invisible College, joins the show with Scott Kitun. Nick comes on to talk about the colorful but often opaque world of Web3. Everyone seems to be talking about it but what is Web3 and how do you become a participant? These are just some of questions Nick set out to answer when he created Invisible College, an education platform to understand the basics of Web3 that includes purchasing a reasonably priced NFT you'll use to understand ownership and participate in the digital community. Scott and Nick talk about how everything moving online has accelerated the development of Web3 products, why cryptocurrencies and the flow of digital assets are worth your attention and how Twitter became a "serendipity engine".  They also talk about the importance of timing, following trends and getting to a proficiency where you can separate the noise in our increasingly blockchained world. 

Paige Finn Doherty joins the show with Scott Kitun.  Paige is a founding partner of Behind Genius Ventures and author of a  children's book - for adults! - about investing called Seed to Harvest. Paige talks about her journey into venture and her realization that you don't need to come from generational wealth to invest as her founding thesis. Scott and Paige talk about how much the pandemic has shifted identities and made it easier to form investing communities. They talk about how the story of investing is a story of the internet, how digital hoarding has becoming a growing trend and the ability to make any asset liquid. 

Brian Saunders, founder and CEO of BigTime Software, joins the show with Scott Kitun. BigTime provides turnkey billing software solutions for professional service firms and consulting services that makes it easy to capture billable hours, allocate and manage project resources and consolidate key metrics. Earlier this year, BigTime took a $100 million strategic investment from Vista Equity Partners for new product development and expanding customer-facing teams. Brian shares his journey in IT consulting and 20-year ride with BigTime. He talks about pattern matching as a foundation for driving success and helping people get paid faster. Scott and Brian geek out over the plight of founders, fair and unfair criticisms and why founders tend to be four steps ahead. 

Otto Othman, founder and CEO of Pincho, joins the show with Scott Kitun. Pincho is a street-food inspired burger and kebab shop based in Miami, Florida.  Otto, a former UX designer, talks about the origin story of how he and his cousin originally came up with a plan to sell his mom's pincho kebab recipe by opening up Pincho (formerly called Pincho Factory). Born and raised in Brazil, Otto says Pincho is basically a Latin twist on American classics like burgers, kebabs, chicken sandwiches (salads too) and hot dogs...getting hungry yet? In this fun foodie conversation, Scott and Otto get into the food industry and how to scale a business like Pincho similar to Chicago's iconic Portillo's food chain. Otto talks about how his background in tech helped fuel Pincho's growth during the pandemic - a time when many restaurants are struggling - and growing the fast-casual concept, or as Scott likes to call it, "the athleisure of restaurants". Pincho recently raised $20 million from Savory Fund  to rapidly expand its presence across multiple states in Florida and Texas. 

Doug Ludlow, co-founder and CEO of MainStreet, joins the show with Scott Kitun. The greatest need for any startup is almost always a combination of time and money, often more money to buy more time. MainStreet aims to help solve the problem by working  with startups to save on operating costs across the board. From tax credits to specialized discounts, MainStreet gathers all the opportunities a startup can take advantage of that can save possibly several hundred thousand dollars (or more) per year. Doug talks to Scott about supporting founders and why something like MainStreet is a no-brainer for companies at the early stage. Doug walks through how his years as an entrepreneur and time at Google -where he met his cofounders- set him on the trail to helping more startups get off the ground.  Scott and Doug chat about increasing  runway, freeing up money to make key hires and make more startups that fail become successful businesses. 

Clarence de Silva, CSO at Stable.work, joins the pod with host Scott Kitun. Sales is often considered one of the most crucial components of a business, but also the first to go when times are tough. In the era of the gig economy, remote, seasonal sales professionals are an increasingly appealing plug in for companies. Marketplaces like Stable.work exist to do just that: provide on-demand sales professionals to companies in times of need, and give sales people the ability to pick and choose their assignments that best fit their attributes. Clarence and Scott talk about the importance of sales, how attitudes towards the sales role have changed, and finding the right place for sales in your company. They also talk about differences sales processes, referrals and how sales pros have never had better opportunities to make a side hustle become their main thing. 

Sam Rosen, co-founder and CEO of Deskpass, joins the pod with Scott Kitun. Every year, even every few months we start seeing the "when are we going back to the office?" trend on the timelines and wonder if this will be the time the legions of white collar workers return to an office-centered lifestyle. Do people want to be back in office full time or not? Turns out as the statistics, cultural desire and the Great Resignation have shown, the future is  hybrid models. Sam and Scott have an excellent conversation cutting through the fog of return to office myths, and why employers are best suited meeting their teams where they live. They dig into how hub and spoke leasing models work and where commercial real estate continues to play a role in the new normal.  Sammy also shares how companies like Moderna are using his company Deskpass as a remote solution. Deskpass provides on-demand leasing, which allows employees to reserve office space when and as they need it. 

Anders Jones, co-founder and CEO of Facet Wealth, joins the show with Scott Kitun. Facet Wealth is a fintech company offering personalized financial advice and wealth management services. Today, Facet announced a $100 million  Series C round led by Durable Capital Partners LP  to fuel its growth with users, team and tech suite. Through a combination of proprietary tech and access to CFP (Certified Financial Planner) professionals, Facet wants to serve an underserved market of 40 million American households with an affordable subscription model (as opposed to AUM-based fees). Anders talks to Scott about securing the Series C and how he and his cofounders came up with the idea helping their mothers he likes to call "The Tale of the Three Mothers". Scott and Anders talk about changing the standards of financial literacy in the US, changing public perceptions around debt (it CAN be a tool) and offering more sophisticated financial advice than retail investors are privy to through apps like Acorns. They also touch on the rise of meme stocks, the future of retail investing and why fintech companies like Facet have the opportunity to serve underserved populations differently. 

Matt Massucci, co-founder and CEO of Hirewell, joins the show with Scott Kitun. Hirewell is a recruiting platform that connects employers with prospective talent nationwide.  The company just received a $21 million strategic investment from  global investment firm Pyrtek. Matt shares some of the details and how Hirewell is focusing on tech, growth, and acquiring an Israeli software startup ICV. Scott and Matt talk about the state of recruiting two years into the pandemic, the hot, Hot HOT job market (for tech professionals especially) and how companies can find a better way to stand out to prospects in a candidate's market. Matt also talks about about the  20-year journey he's been on since founding Hirewell, how tech went from a small niche in recruiting to the mainstream, and why he feels the company is in the spot he always envisioned. 

Joe Reinke, founder and CEO of FitBUX, joins the show with Scott Kitun. Joe gives the the pitch on FitBUX, an automated software solution to financial planning. From student loans to stocks, FitBUX measures your financial data and provides easy-to -understand analysis for you to make money decisions. Scott and Joe talk about the future of investing, the growth of retail investing and why financial planning is due for sizable disruption. Joe shares how FitBUX combines automation with a human connection, providing coaching to users to best use the software and harness results from the data. FitBUX is currently raising a round in the crowd on Republic. 

Gabby Cazeau, Principal at Harlem Capital, joins the show with Scott Kitun.  Harlem Capital is a venture capital firm with a core mission to invest in a  thousand diverse founders (including Chicago's very own CASHDROP) over 20 years and  change the faces of entrepreneurship. Gabby shares her journey from intern to Principal at Harlem Capital and how she's been supported to follow her interests finding solutions to inequalities and strengthening communities. Scott and Gabby dig into the state of venture capital today, helping founders pass by bad investors, and creating a broader understanding for what a diverse tech ecosystem looks like. Gabby is currently interested in companies dealing in ecommerce, fintech and software.

Leore Avidar, founder and CEO of Alt, joins the show with Scott Kitun.  As cryptocurrencies have exploded in popularity so has the rise of other forms of alternative assets like NFTs, wine and sports cards. Alt is one of the platforms leading the charge in making trading cards an investable commodity, with the idea of making everything investable a liquid asset. Leore talks about the origin story for Alt when he tried to get a bank loan against his cards (spoiler: the bank didn't accept) and set him on a course to legitimize cards as currency for longtime fans and retail investors alike. Scott and Leore get into the future of cards, liquid auctions, how to make banks fun and thinking through the customer experience from beginning to end. 

Pek Pongpaet, founder of impekable and longtime Technori alum, joins the show with Scott Kitun. impekable provides UX design services to tech companies, including work with  Adobe and Twilio  among many others. Pek talks about his journey from Chicago to the Bay Area (and back again), how design has been mainstreamed into tech, comparing the talent landscapes between Chicago and Silicon Valley and how much the vibe in Chicago is changing. 

Will Glaser, founder and CEO of Grabango, joins the show with Scott Kitun. Prior to founding Grabango, a check-out free technology for grocery stores and convenience stores, was the co-founder of Pandora, one of the pioneers in digital music streaming. As the son of a college professor and a psychoanalyst, Will has had a lifelong tug of war between the left and right side of his brain. He attributes this tug of war to his main interest starting companies at the intersection of technology, consumer impact and business. Will talks about how focusing on this trifecta gives him a business model blueprint for developing startups, how it links Pandora and Grabango and solving consumer pain points. Scott and Will share their thoughts on best hiring practices and why founders should be prepared to step aside (eventually) from their companies in order to sustain its development. Will also dives into Grabango's shopping experience, how it compares to Amazon Go and why checkout-free technology is poised to take over mainstream brick and mortar shopping experiences. 

Pete Wilkins, Managing Director at Hyde Park Angels and author of Purpose + First Entrepreneur, joins the show with Scott Kitun.  Over the course of his career, Pete has worked with all kinds of business leaders, young founders and everyone in between. One of the main drivers of success (and failures) he's observed in his own life and others is working each day with the idea of purpose. The goal for Pete is simple: help more people love who they are and what they do. With the framework of purpose laid out in the book (and accompanying workbook), Pete creates a path for others to find clarity in their work objectives, personal wellness and unlock your highest performance. On the show, Scott and Pete talk about their their own trials and tribulations, how to take care of yourself and how Pete put together the Purpose First structure over the last decade. You can find the Purpose First book here. 

Anthony Zhang, co-founder and CEO of Vinovest, a wine investing platform, joins the show with Scott Kitun. The age of retail investing and collecting is upon us and never before have so many people been able to invest in everything from baseball cards to NFTs. Why not fine wines? Anthony answers resoundingly how a long-time collector's item - wine - is a natural  fit as an alternate asset in anyone's portfolio. In a thoughtful conversation, Anthony and Scott walk through the  appeal for wine as an asset class and how Vinovest acts as your marketplace, portfolio, education center and wine cellar. Anthony also shares his journey as a repeat founder and how he googled "what do rich people invest in" when he first started to personally invest and eventually that started spurred the idea for Vinovest. Anthony and Scott also talk about the similarities to buying/storing cards  like Alt. Anthony recommends what wines anyone should start with and how to on the platform based on when you want the best ROI. You can follow Anthony on his Twitter for wine info and advice. 

David Cheng, Principal at DCM Ventures, joins the pod with Scott Kitun. The role of VC isn't the same as your father's, or even your grandfather's VC anymore. No longer is venture capital only about getting a check once and being hands off otherwise. As we've started to see with a16z and rolling funds, DCM's methodology is to play a hands on role with founders in clear, specific niches to grow an idea into a full grown business. David and Scott talk about the changes in VC and why there is an increased expectation on a firm and its associates to earn a board seat by playing an active role in the company, providing resources, strategy almost like a fellow co-founder. David shares his experiences working with companies (primarily in fintech and health tech), how the future of investing is starting to turn into full incubation, "pre-idea" stage by essentially recruiting entrepreneurs to start companies and build businesses from the ground up. Scott and David also dive into emerging tech, role of crypto, where to start with web3 and more. 

Tony Sheffler known for his trading expertise and founder of employee happiness and retention company HappyWork, joins the show with Scott Kitun. Tony and Scott kick off the pod with an all-encompassing conversation on #thehobby, what the differences are between PSA, SGC and why SGC is in such a good position to really shine in the market. They talk about Fanatics entry into the world of trading cards, why they aren't going anywhere and seeing what they have to do to get Alt or Fanatics to sponsor the show. In the second half, Tony dives into employee retention and how he and his cofounder evolved the idea of the company over time to reach workers better with a messaging program. Scott and Tony go back and forth on why survey-based assessments of employee happiness only shows you what's happened in the past and usually doesn't show what employees are concerned about in real-time before they leave the company. HappyWork is a tool that can be used to increase employee reach and engagement, awareness of work benefits, and more. 

Sahil Lavingia, founder and CEO of Gumroad and author of the new book "The Minimalist Entrepreneur" joins the show with Scott Kitun. Scott and Sahil share their passion for the changes coming to investing such as equity crowdfunding and retail investor movement. Sahil earlier this year raised $5 million in one of the fastest filled rounds ever on Republic, and plans to open up future crowdfunding rounds when needed. Gumroad is a digital marketplace where users can sell memberships, courses, books and other services and is built on the idea that creators can control their own business infrastructure by building an audience and using an internet connection. Sahil talks about the long journey for Gumroad, why investing is increasingly liquid, and how crowdfunding as a tool will need continued support and development from the private sector (entrepreneurs, platforms) and incremental modifications in policy from the government. Scott and Sahil also talk about his book (released Oct 26th) and how his experiences, beliefs and conviction that entrepreneurs need less than they think they do to get started and laying out simple steps for founders to build their businesses. 

Brian Morrissey, former President/EIC of Digiday and current writer of the media business Substack The Rebooting, joins the show with Scott Kitun.  They get into it all things  media and the business of media, and how this period of upheaval with the pandemic is a chance to get things right and inspired The Rebooting name. Brian talks about changes that should happen - both in media companies and companies in general - and much of it has to do with accepting less control over employees (i.e. work from home and other benefits). They talk about how being so much more online helps people learn to identify scams, how different generations view work and how we can fix problems in the US that have broad agreement without falling into tribal arguments. Scott and Brian chat about how crypto could play an important role in addressing media business models and a litany of life topics: running, bachelor parties, looking back at the last three decades, serial killers in the 80s and more!