The aSaaSins Podcast

In this episode of The Bridge, Justin sits down with Jessica Collier, CEO of Spot, and founding partner of All Turtles, to explore her journey from academia to building one of the most thoughtful AI-driven tools in the HR tech space.Jessica was the first UX writer at Evernote, where she helped shape user experiences through words before it was a recognized craft. She later went on to co-found All Turtles, alongside Phil Libin (former Evernote CEO) and Jon Cifuentes, with a mission to build practical AI applications — long before the current hype cycle.In this conversation, Jessica shares:The early days of bringing AI into product workflows before it was coolHow Spot is reshaping the case management and incident reporting category with anonymous, AI-powered reporting tools for any case typeWhy “trust” is the foundation of any product solving sensitive problemsThe build vs. partner decision framework when enhancing core functionalityLessons from scaling multiple ventures rooted in ethical product designWhether you're an operator building with AI, a founder evaluating product scope, or someone navigating tough conversations in the workplace — this episode offers tactical insights and big-picture clarity.

Brett Beveridge, Founder & CEO of T-ROC, joins the show to share his journey from bouncer and bartender to building one of the largest retail operators in the U.S.We dive into:How he started selling cell phones out of a van and took Let's Talk Cellular public before selling to NextelWhat's fueled his 20+ year run building T-ROCHis take on when to expand product lines — and when to stay focusedHow to think about funding: bootstrapping vs. venture capital

Tessa Brown, Co-Founder and CEO of Germ Network, joins the show to talk about, - Tessa's journey from Stanford writing professor to startup founder, the dangers of social platforms designed to maximize exposure, and why privacy should be the default, not the exception.- How Germ lets users create multiple, compartmentalized identities- The flaws of phone number–based messaging and the case for link-based connection, and her philosophy on building with integrity in a surveillance-based tech world- Tessa's experience fundraising from K5 Global and Mozilla Ventures

Jared Robin, Co founder of RevGenius and Audience Haus, joins the show to talk aboutJared's first sales job, cold calling office managers at FedEx to building a fashion blog with 10K monthly subscribers.The art of audience building, and how a LinkedIn group chat turned into an engaged 50,000 community What does it take for a B2B company to successfully build an audienceReflecting back on the presidential election and lessons learned in audience building.The trends of B2B SaaS companies purchasing media businesses and the future of enterprise content.

Chris Andrew, Co founder and CEO of Scrunch AI, joins the show to talk aboutThe evolution of search and consumer shift toward finding answers with AI.Building a marketing platform for an AI first customer journey.The opportunity for AI and Scrunch to audit search and help brands manage their identities in the era of AI.Reflecting on Chris leaving Intuit to work for Clara Shih at Hearsay, and what Chris learned from Clara as employee #3 at Hearsay that made him a better entrepreneur. A wild car ride with Gary Vee when Gary first launched Wine Library TV, and pitching Gary Vee a cooking show.

Tatiana Fofanova, CEO and Co Founder of Koda Health, joins the show to talk aboutFrom pediatrics to entrepreneurship, and Tatiana's experience as a founder in residence at Texas Medical Center (TMC)The intersection of the law and health, and building an advanced care planning tool that is patient centric.Becoming "patient zero" for Koda Health after being hit by a car and getting diagnosed with kidney cancer, all in the same afternoon. Designing Koda's go-to-market strategy in health care, and how Tatiana has thought about building out her team in a healthcare startup.

Conor McCarter, Co founder of Prequel, joins the show to talk about:The founding story behind Prequel, the YC experience, and pivoting during the program.Market overview on the state of data management and positioning of Prequel.The fundraising process for Prequel and importance of not beating yourself up as a founder and staying creative amidst the grind.

Dr. Maheen Mausoof Adamson, CEO and Co founder of Soof Solutions, joins the show to talk aboutThe intersection of neuroscience at Stanford and entrepreneurship, and path to founding Soof.Building Soof to help her father speak again after experiencing a stroke in 2007.The importance of timing and how Apple's advancements in hardware openned up the market for Soof.How Dr. Adamson worked with Stanford and the biodesign program to apply research and real patient interacton insights to build their venture.How to leverage your investors and advisors to complement your team's strengths.

Megs Shah, CEO and Co founder of Parasol Cooperative, joins the show to talk about:Surviving abuse and founding Parasol Cooperative to battle a growing, global, shadow pandemicKeeping our kids safe online, and the insights that led Megs to building her two products, SafeConnect and Ruth solutions overviewDiddy's downfall, the shift toward disconnecting and digital minimalism, and the responsibility of developers to consider safety of your end users up front. 

Dr. Jennifer Hintzsche, CEO and Founder of PherDal, joins the show to talk about:- Dr. Hintzsche's personal story of being defined as "in-fertile", a $10,000 invoice for a solution to a problem that doctor's couldn't define, and how she used her PhD to prove those physician's wrong.- The process of crowdfunding for PherDal and lessons learned by launching on their platform. - Market sizing the fertility market, dealing with the FDA, and going from 0 to 1 in biotech. 

Daniel Saks, Co founder and CEO of Landbase, joins the show to talk about- Growing up in an entrepreneurial family in the business of furniture and the insight that led to founding Daniel's first business, AppDirect.- The importance of establishing "go-to-market credibility" before engaging in sales outreach. - Daniel's experience fundraising for AppDirect, and most recently Landbase's $12.5M seed round.- The importance of "founder-market" and "founder-product" fit.

Alex Douzet, CEO and co founder of Pumpkin, joins the show to talk about- Building his first company Ollie, in the pet food and delivery space, and how doubling down on his experience in pet care and the "humanization of pets"  led to founding Pumpkin- Picking the brand name "Pumpkin" and the importance of building flexibility into what you ultimately call your business. - The decision to focus on quality of care and alignment with the veterinary community to grow and scale Pumpkin.- Unpacking the psyche behind a 7 time ironman and a three time founder, embracing the pain cave, and near death experiences in company building

In this episode Justin sits down with Nico Simko, the dynamic CEO and co-founder of Clair, a trailblazing company set on revolutionizing on-demand payroll. Nico shares an inspiring narrative from his beginnings as an economics tutor to spearheading a fintech powerhouse. We uncover how Clair smartly embeds on-demand pay within HR platforms, bypassing the conventional approach of targeting employers or employees directly. Nico also articulates the challenging yet rewarding journey of building Clair into a secure and compliant fintech solution, highlighting the crucial art of maintaining focus and discerning when to say no.As we explore the intricacies of Earned Wage Access (EWA) services, Nico offers candid insights into navigating the intricate regulatory maze. We dive deep into the significance of foresight in compliance and how strategic partnerships bolster Clair's success amidst evolving financial regulations. Nico's vision stretches beyond the present, painting a picture of a generational fintech company that could redefine employer-linked financial services. This episode is packed with wisdom for entrepreneurs eager to grasp fintech opportunities, and we wrap up with a teaser for our next episode featuring an innovator making strides in the pet tech world.

Tim Fung, Co founder and CEO of Airtasker, joins the show to talk aboutHow an apartment move led to the founding of Airtasker.How tasking and labor markets differ globally, and what this market looks like in Australia.How Airtasker is focusing on localization and community to differentiate from platforms like Fiverr and Upwork.Finding product, channel fit, and how Airtasker used regional media outlets to drive awareness in local markets to create local jobs.

Dr. Lewis Bernstein, Co founder of 3G and former executive producer for Sesame Street, joins the show to talk about:Dr. Bernstein's early work at Sesame Street, working alongside Jim Henson, and how the mission and message of Sesame Street has evolved over time.The founding story of 3G and using multiple generations to help combat loneliness in our youth.Current state of children's programming and content. How it has evolved for better and worse. The future of early stage childhood education

Tad Milbourn, Founder and CEO of RankedVote, joins the show to talk aboutThe momentum that's building around ranked choice voting. What it is, how it works, and why it's a better method of getting consensus.Lessons learned from Tad's first company, Payable, the YC experience, and navigating a successful exit and selling to Stripe."Upgrading state and federal elections".  An election software market overview and current state of election reform at state and federal levels.Eliminating friction in the user experience to build stronger advocates for ranked choice voting. Tad's decision to start RankedVote as a solo founder, and the differences in the founder journeys between Payable and RankedVote.

Jon Staenberg, Founder and CEO of Agate Hound Fund joins the show to talk about Growing up in Nebraska to Silicon Valley to Microsoft to VentureHow Venture Capital has changed and the rise of the Search Fund.What is a "Search Fund" and the reason behind why it's such a successful asset class.The Silver Tsunami and baby boomers without an exit plan.The criteria that Jon has established for the successful businesses he backs and the traits that his funds look for in the entrepreneurs they invest in.Launching "Hand of God" wines and challenges of building an independent wine brand.

Travis Schoen, Founder of NW Golf Guys joins the show to talk about:How Travis moved from scoring free golf to starting a golf league and growing its member base to more than 7,000 members.How the game of golf has evolved over the past 20 years, and how NW Golf Guys thinks about their target demographic and approach to member acquisitionWhat goes into putting on a great golf tournament, the greatest golf movie of all time

Sahand Dilmaghani, Co founder and CEO of Terra Kaffe, joins the show to talk aboutBuilding the worlds most beautiful and intelligent espresso machine, and the process that went into prototyping a better coffee experience.Balancing development for the software user interface and the human machine interface, and the two journeys people take when brewing their coffee.How Terra Kaffe thinks about the competitive landscape in coffee, and how Sahand is approaching partnerships in the coffee category.How Sahand and team are helping reduce ecological waste and helping customers "kick the pods", one cup at a time.

Jordane Giuly, CEO and Co founder of Defacto, joins the show to talk about- Jordan'e experience building a Unicorn at Spendesk and the decision to walk away from the successful startup he co-founded.- The three bets that Jordane and team are making to go big with Defacto.- Building his startup in Paris vs. Silicon Valley, and the benefits of building outside of the US.- Lessons learned from fundraising for Defacto vs. Spendesk, the importance of balancing transparency and confidence when going through challenging times, as well as the importance of remembering to find joy in what you're building.

Martin Pannier, Co founder and CEO of Primo joins the show to talk aboutLessons learned building product at Gusto that led to solving for the "accidental IT Manager"The decision to launch a free product SKU, PLG, and considerations to make before launching a free productThe pros and cons of building your startup pitch with your VCs. 

Parker Gilbert, Co founder and CEO of Numeric, joins the show to talk about- How going through a challenging financial audit led to the insight of founding Numeric.- The character traits that Parker looked for in his co founders for Numeric.- Parker's experience closing is $10M Series A and what it took to close a round from Founders Fund, Menlo Ventures and how he iterated to build a pitch that ultimately landed.- Signing customers that can help Numeric accelerate partner growth, and the "why now" answered for Numeric.

Carin Luna-Ostaseski, Founder of SIA Scotch Whisky, joins the show to talk aboutThe process Carin went through to kickstart the SIA brand, and being the first hispanic woman to found a Scotch brand.The state of the spirits industry and how SIA positions itself and competes with other liquor brands in the beverage category. The "bonsai tree" method of building your company, and the importance of "starting in your own backyard" when launching a brand.

Adam Katz, CEO of Sightly, joins the show to talk aboutAdam's journey from IC to becoming the CEO at Sightly and leading from the frontThe evolution of the marketing tech category and generating an authentic brand voice in the era of AI.How Kobe Bryant inspired Sightly's Brand Mentality vision and narrative.Caitlin Clark and the future of the WNBA brand and women's sports.Defining your brand through what you say AND what you do.

Andrew Firestone, CEO of Mermaid Chart, joins the show to talk about:The venture studio model and building Mermaid Chart out of Open Core Venture Studio.Stepping into the CEO role at Mermaid and building an open-sourced approach to the diagramming and creator tools industry.Unlocking go-to-market and investing in channels that create accumulating advantages for Mermaid.Lessons learned from raising capital and taking 300 meetings in four months for Mermaid Chart (and eventually closing a round with Sequoia, Microsoft and OCV)

Matt Wadiak, Co founder and former COO Of Blue Apron, and CEO and Co founder of CleanUp joins the show to talk about- Founding Blue Apron and being one of the first movers in meal planning and e-commerce ingredient market. - The importance of capital planning and cash flow and the importance of picking markets.- Key ingredients to succeed as an entrepreneur in the food space.- How customer acquisition has evolved in the D2C space and what founders can do to ensure the cream rises to the top. 

Harry Tannenbaum, Co founder of Mill,  joins the show to talk about.Harry's experience at Nest and building products that are really good for that planet.The Mill process of finding PM fit as a hardware startup.Harry's decision to go DTC, "core vs. context", and how he thinks about evaluating BD and partnership collaboration opportunities Lessons learned from Harry as a first time founder and the importance of ideating tactfully. 

Joel Pollick, Co founder and CEO of Percent Pledge, joins the show to talk aboutThe three main challenges that consumers wrestle with when it comes to giving back.Building a culture of giving, shifting from paycheck to purpose, and a generation that gives moreThe importance of reinforcing your mission...over, and over again.  

David Sauers, Co founder of Royal Restrooms, joins the show to talk about:A porta potty mishap that led to building one of the largest and most successful portable sanitation companies.The explosion of the sanitation market post-COVID, and the market opportunity in public restrooms.Maintaining a high level of professioal services while scaling Royal Restrooms.Royal Restrooms franchise model and what David looks for in business partners to expand the company's footprint.

David Meltzer, author, coach, speaker and co founder of Sports 1 Marketing joins the show to talk about:Growing up in a family with "not-enough" to a $3.5B exit and building the most successful sports  agency in the world. Losing everything (>$100M) and having to rebuild a sense of purpose in the founders' journey.Dave's model for prioritization and time management, as well as ways to create a better working relationship and deeper connection with your partner/spouse.

Chris "Tito" Sestito, CEO and Co founder of HiddenLayer, joins the show to talk about- How prepared (or unprepared) companies and our government is for the evolution of AI- Raising a $50M round from Microsoft, Booz Allen Hamilton, IBM, and Capital One, and Chris' thoughts around building a business with strategic capital and partnerships.- How Tito and team think about prioritizing what HiddenLayer works on when the total addressable market is HUGE and customers want it all, now.

Tom McLeod, Founder and Executive Director of Arkive, joins the show to talk about:Re-imagining the art museum and the founding story behind Arkive.Breaking down the collectibles space and the evolution of NFT's and digital creative works.Lessons learned from shipping 17 iPhone apps, and measuring "speed to learning" as Tom's ultimate KPIWhy the wave of Gen AI apps is very different than the rise of mobile apps.Keeping love, passion, and business separate.

Guy Kawasaki, evangelist and author, joins the show to talk about- From Kalihi Valley to Apple.  The first bridge that Guy took to success that started in the 6th grade. - What is a product evangelist and how should early stage founders be thinking about evangelism?- Guy's definition of what it takes to be remarkable (and what it isn't), what it was like working for Steve Jobs, and how Steve Jobs showed him what being Remarkable looked like. - Guy's Golden Touch, what "golden looks like", and how Guy decides to get involved in the projects he works on.- The keys to being a successful nonfiction author and when to borrow and/or steal.- Growth, Grit, and Grace - and his book "Think Remarkable" 

Ariel Renous, Co founder and CEO of Augment joins the show to talk aboutHow Augment is disrupting the traditional MBA program.Fundraising for Augment and $6M from RTP Global. The future of executive education, and the importance of learning and raising money from people that have actually done the thing.

Baron Davis, Founder and CEO of B.I.G (Business Inside the Game), joins the show to talk about:Baron's "renegade approach" in transitioning from NBA All-Star to entrepreneurship.The importance of investing in "multi-hyphenates", and how B.I.G is building its network around creators with these super powers.Who were some of Baron's early mentors and advisors as an entrepreneur, and what entrepreneurs should be looking for in mentorship.Baron's perspective on the future of the business of basketball, where we're at in terms of the quality of the game, and what he wishes he would have known as a rookie before entering the NBA and entrepreneurship.

Eve Halimi and Anam Lakhani, Co founders of Alinea, join the show to talk about:The challenges of managing money out of college & founding Alinea.Taking Alinea to profitability before their seed round.Slackers vs. trackers and how Gen Z compares to prior generations of money managersWays to teach my kids how to be financially literate.The role of co-CEO and how Eve and Anam divide and conquer.

Kamakshi Sivaramakrishnan, CEO and Co founder of Samooha (acq'd by Snowflake), joins the show to talk about- how she built two companies that helped customers "bring data to life", selling DrawBridge to LinkedIn and Samooha to Snowflake.- Kamakshi's advantages as a second time founder.- How Kamakshi knew it was the right time to sell Samooha and the process she went through in the acquisition with Snowflake.- Leadership differences between the leaders of the companies that Kamakshi sold to, most notably, Satya Nadella (Microsoft) and Frank Slootman (Snowflake)- Betting on the Snowflake platform, the importance of partnerships and dating before marriage, and the pros and cons of a single platform approach.

Albert Gozzi, CEO and Co founder of Aleph joins the show to talk about. The insight Albert got from his time in consulting at Bain, specifically the pain in and around FP&A (Financial Planning & Analysis), that led him to founding Aleph.How CEOs should be thinking about balancing "relationship building" with VCs vs. building the business. The mentality of company building after closing a Series A, and balancing resource allocation across product development and growth.

Nora Jones, CEO and Co founder of Jeli, joins the show to talk aboutHow Nora's experience at Jet, Netflix, and Slack led her to founding Jeli.Chaos engineering, quantifying the impact of burnout in an "always on" economy, and the human side of incident management.  Selling Jeli to PagerDuty and the process Nora went through to sell the company (when to bring in outside help)

Tracy Young, CEO and Co founder of TigerEye, joins the show to talk aboutBuilding Tracy's first successful company, PlanGrid, and how the Autodesk acquisition of PlanGrid led to Tracy uncovering the opportunity for her current venture, TigerEye (launching this year in 2024!)Tracy's decision to start another company and how she evaluated her options after her time at AutoDesk.Balancing family and founder responsibilities, the efficiencies gained when time is in limited supply.Scaling beyond boundaries, and the cost v. benefit of building a team that is in-person v. remote.Heightened expectations as a second time founder, learning to listen more, and a better way to build and forecast revenue.

Anna Believantseva, COO and Co founder of Esper Bionics joins the show to talk about - Human augmentation and using bionics and technology to extend our human potential.- The human technology stack, and the potential of embedded hardware in humans. - The role of a COO at an early stage startup, B2B2C business model challenges and fundraising for a bionics, robotics, and hardware startup. 

Hedda Båverud Olsson, CEO and Co founder of Lassie, joins the show to talk aboutThe Pet insurance and pet ownership space, the major insurance incumbents, and Lassie's focus on preventative veterinary practices.Chicken problems and how different cultures view pet ownership. Hedda's experience closing out her €23M Series B round from Balderton Capital, and best practices on how to close your round efficiently.Hedda's experience in the music business, and how it helped her become a stronger entrepreneur.

Rachel Blank, CEO and Co founder of Allara Health, joins the show to talk aboutThe evolution of women's health care and how improvements are being made through digital health.The importance and advantages of a "direct to consumer" health care model.Raising $10M from Google Ventures, balancing cash conservation with growth, and how Rachel is thinking about scaling quality of care as she grows her team.

Mike Weiland, Co founder and CEO of Govly, joins the show to talk aboutWhy selling to the government is really hard and how Govly makes that easier for businesses contracting with the government.Raising $9.5M Series A from Insight, fundraising for a government tech startup, and the advantages of picking a more unique venture vertical that is recession proof.Raising the bar and challenging employees to achieve more, and how Govly did that to hit their revenue milestones ahead of raising their Series A.Founder/VC fit, and some of the proof points that validated that Insight was the right partner to help Govly scale its company.

Navneet Dalal, CEO and Co founder of Matic joins the show to talk aboutBeing an early mover and pioneer in computer vision and deep learning.Moving beyond an interface and a good product to build a lasting, sustainable business.Being acquired by Google, working for Tony Fadell and with the Nest team, and the insight that led to Matic.The "human sensor stack" and how it intersects with the "robot sensor stack", and why Matic started with cleaning the floors.Picking an existing market and the importance of building a "minimum loveable product".

Sam Chaudhary, Co founder and CEO of ClassDojo, joins the show to talk aboutWhere early stage education is falling short, and Sam's experience building the largest community for teachers, parents, and kids to thrive in the educational system. The process Sam and his co founder Liam went through to unlock PM fit for ClassDojo.The jobs left to be solved in education, reflecting on the COVID home school experience, and how ClassDojo is expanding into the Virtual Learning Experience to solve the jobs that the classroom won't (or can't do well).

Siva Namasivayam, Co founder and CEO of Cohere Health, joins the show to talk aboutStarting companies in chaos and a family full of MDs.The inefficiencies that exist in the operational side of Health Care.Identifying early adopters and the nuances of doing that in a more conservative market like Health Care.Raising capital in health care and the traction you need and expectations you need to set before going out to raise capital in Health Care.

Mallory Greene, Co founder and CEO of Eirene Cremations, joins the show to talk about"Death tech" and growing up in a family business centered on death.Why death is a great business, and the metrics that matter when raising capital in the Death Tech spaceBuilding an "honor based" mindset to servicing the families who have lost loved ones.

Tony Jamous, Co founder and CEO of Oyster, joins the show to talk aboutGlobe trotting from Lebanon to France to Cyprus, and the pains of starting a globally distributed business and the founding story of Oyster.The assumptions and excuses of an in-person office cultureA purpose driven approach to company building, and why Tony built Oyster as a B Corp.Hiring the right people for the C-suite, and how Tony has approached executive hiring at Oyster.

Farzad Rashidi, Co founder of Respona, joins the show to talk about:The process Farzad went through to calculate customer acquisition costs and find the channel that ultimately led to founding Respona.A brief history of SEO, and a few hacks that founders can apply to grow their business.Tactics for podcasters to grow their own listener base + how Farzad landed an interview on this show.Balancing speed with quality, and when is "too early" to ship your product?

Daniel Yanisse, Co founder and CEO of Checkr, joins the show to talk aboutThe insight from building a startup in the gig economy to founding Checkr.Eliminating bias in the hiring process to help prospective hires live the dream.How founders should evaluate M&A opportunities and when it makes sense to acquire another company.Going up market into selling to larger enterprise with your productFlying high and flying low. When and how a founder should get "in the weeds" when running their company.