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.