Episode Stack: https://stackl.ist/4qaixcK

Summary

In this episode I sit down with Vlad Cazacu, Founder and CEO of Flowlie, to talk about the long, winding path that led him from an immigrant kid obsessed with science magazines to building one of the most thoughtful fundraising tools I’ve used as a founder.

We go way back. Before Flowlie was helping founders raise hundreds of millions of dollars, Vlad was running a textbook startup in college, turning down an acquisition offer because it did not feel big enough at the time. That early mix of curiosity, naivety, and ambition shows up again and again in his story.

Vlad spent years on the investing side, working in venture capital and family offices, seeing thousands of deals and learning how capital actually moves. Flowlie did not start as a founder product at all. It began as an internal tool for investors, then pivoted after founders started asking a simple question: “Are we even a good fit for these investors?” We talk about the shoebox office in Miami, the moment Stripe lit up with their first paid users, why fundraising is mostly unnecessary overhead, and how AI should remove friction instead of adding noise. This is a true zero-to-something story, told while still very much in motion.

Key moments we cover:

• Growing up in Romania and falling in love with building through curiosity
• Building and shutting down a college startup after turning down an acquisition
• Writing a book before ChatGPT and how it unlocked a VC career
• Why Flowlie started as an investor tool and pivoted to founders
• The first Stripe notification that made everything feel real
• A future where founders only show up for investor meetings

Key takeaways:

• Naivety is often a feature, not a bug, in early founders
• Fundraising is a system problem, not a confidence problem
• The right tool removes emotional and cognitive overhead

Chapters

00:00 The Naivety of Startup Beginnings

03:03 The Journey to Entrepreneurship

06:07 The Birth of Barter Out

09:01 The Influence of Family and Curiosity

12:04 Lessons from Early Ventures

14:55 Transitioning to Venture Capital

17:58 Building Flowlie: The Next Chapter

22:57 The Pivot to Founders' Needs

30:00 Building the Team and Culture

37:05 Funding Journey and Growth

38:13 Future Vision and AI Integration

Episode Stack: https://stackl.ist/48R3vkY

Don't miss this episode. I loved this conversation with Stephen Messer, who co-founded LinkShare with his sister in the late 90s and sold it to Rakuten after about 10 years. He's now building Collective[i], an AI platform that makes your professional network actually usable.

Stephen walked me through the first four years of LinkShare when they lived in one apartment, rotated shifts on two computers, and he worked directly on the main server because they couldn't afford another machine. During their pitches they had to spend first hour explaining what the internet was before they could even talk about the business. Revenue didn't grow until year six or seven because they charged 2% per transaction and needed massive volume.

One of my favorite stories: Michael Dell called him on a Sunday night and Stephen thought it was a prank for 30 minutes. That partnership changed everything. The first retailers all said "call us when you have affiliates," but direct marketers like Omaha Steaks understood the model from catalog days and signed up first.

Stephen was honest about why the skills from one successful company don't always transfer to the next one, why venture capital from top-tier firms isn't always worth the price, and his one rule for founders: never live above the second floor because the emotional swings will make you want to jump out the window at some point.

His take on most startup advice: ignore it and find your own style. Really appreciated Stephen's time and honesty about what building actually looks like.

Episode Stack: https://stackl.ist/3XlwM1O

I met Tracy in Hawaii when we were midway through our Blue Startups accelerator program. Tracy coaches founders, and also serves as a Mentor in the Blue Startups program.

Tracy came in and told such authentic (both inspiring and difficult) founder stories. We connected after and was thrilled she agreed to join us on Zero to Umm to tell some of those stores.. and more.

Tracy is the Co-founder and former CEO of Chewse, a corporate catering platform she launched from her dorm room, raised $40M for, and successfully sold in 2020. She now serves as an executive coach for founders, helping them navigate the intersection of leadership, mental health, and personal growth.

No matter what stage of the journey you're in, there's something valuable for you in this episode.

Takeaways

• Authenticity is crucial in fundraising.
• Building a startup is an emotional journey.
• Resilience is key to overcoming challenges.
• Staying true to oneself leads to success.
• The importance of a supportive team.
• Navigating the ups and downs of entrepreneurship.
• The role of personal growth in business success.
• Balancing personal and professional life.
• The impact of mentorship and guidance.
• Embracing change and transformation.

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Episode Stack: https://stackl.ist/4307tpO

Summary

In this episode, I had the pleasure of chatting with Rick, a seasoned entrepreneur with a fascinating journey. We kicked things off by discussing the essence of entrepreneurship—how sometimes you just have to dive in headfirst, even if it feels a bit daunting. Rick emphasized that real learning often comes from being thrown into the deep end, which I totally agree with.

Rick shared his early experiences, starting from his time at Radio Shack and how that laid the groundwork for his understanding of business. He talked about how he quickly moved up the ranks and learned the importance of financials, which became crucial later on. It was interesting to hear him reflect on how the landscape of education and job qualifications has changed, especially in tech. He pointed out that today, experience often trumps formal degrees, especially in fields like cybersecurity.

One of the standout moments was when Rick recounted how he launched his first business, "Business PC Help," right after his twins were born. He was motivated by necessity and the encouragement of his wife and a supportive client. He made a great point about the importance of speed over perfection when starting out—he just needed to get something up and running to put food on the table.

As we dove deeper, Rick shared how he transitioned from being a solo entrepreneur to hiring his first employee, Ryan, who he had previously trained at Geek Squad. Their partnership was built on a solid foundation of trust and shared vision, which I found really inspiring. Rick also highlighted the importance of outsourcing tasks that could bog you down, allowing him to focus on growth and sales.

We wrapped up the conversation with Rick's insights on sales techniques, particularly the "assumptive sale" approach, which he learned from his time in fast food. He believes that being consultative and genuinely passionate about what you offer can make all the difference in building relationships with clients.

Overall, it was a rich conversation filled with practical advice and personal anecdotes. Rick's journey is a testament to the power of resilience and the importance of learning through experience. If you're looking to get inspired about entrepreneurship, this episode is definitely worth a listen!

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Episode Stack: https://stackl.ist/3Xg2EoG

I sat down with Jesse Lakes, Co-Founder and CEO of Geniuslink. Jesse shares how he identified a big gap in the affiliate marketing sector and ended up building the preeminent affiliate link solution.

This episode was a fun one. We did have some technical difficulties, a bunch of laughs, and one of the best stories of the 10+ year journey of a startup.

• Discussion of early influences and entrepreneurial roots
• Exploration of how GeniusLink was born from a recognizable market gap
• Insights into the challenges faced during the startup phase
• The significance of team dynamics and established core values
• Reflections on overcoming setbacks and learning from adversity
• Future aspirations for expanding GeniusLink's offerings and impact

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Kyle, Marty, and Will Hubbard discuss the inception and growth of Agree.com, a startup focused on revolutionizing the e-signature and payment process.

They share their backgrounds, the challenges of fundraising, and the importance of collaboration in the startup ecosystem. The discussion highlights the journey from idea to prototype, the significance of securing initial funding, and the vision for the future of the company.

In this conversation, the founders discuss the evolution of their product, focusing on the challenges and improvements made since its initial launch. They share insights on marketing strategies, user acquisition, and the importance of user experience.

They also touch on the future direction of the company, emphasizing the need for continuous growth and adaptation in a competitive market. Finally, they offer valuable advice for aspiring entrepreneurs, highlighting the importance of action and resource management.

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Episode Stack: https://stackl.ist/49o3tk9
(All the links)

Summary

Maxine has quickly become one of my favorite people in the world and this episode was so much fun to make. Her passion for connecting people and sharing knowledge through those connections is easily felt when you talk to Maxine.

We explore the themes of entrepreneurship, collaboration, and the evolving work culture. Maxine shares her inspiring journey from a stable corporate job to becoming a successful entrepreneur, and we discuss the importance of energy, self-belief, and unlocking hidden talents within organizations.

We also touch on the need for a new marketplace that values diverse skills and experiences, and the shift towards a more autonomous work environment. Maxine and I dive deep into the transformative power of conversations, the role of networking, and the potential for platforms that connect kids with professionals to expose them to diverse career paths.

Throughout our chat, we emphasize the immense value of human connections and how they can shape our understanding of the world. This is an episode filled with insights, inspiration, and a glimpse into the future of work and entrepreneurship.

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Episode Stack: https://stackl.ist/4n1utvL

Summary

In this conversation, Tara shares her entrepreneurial journey, detailing the influences that shaped her spirit, the challenges faced while building Rupa, and the lessons learned along the way. From early inspirations to the complexities of team dynamics and the emotional aftermath of selling her company, Tara emphasizes the importance of resilience, gut instinct, and the continuous pursuit of growth in both personal and professional realms.

Chapters

00:00 - Introduction and Context Setting
03:15 - Early Influences and Entrepreneurial Spirit
09:19 - Career Beginnings and Lessons Learned
15:53 - The Birth of Rupa and Vision for Healthcare
21:03 - The Birth of a Non-Alcoholic Bar Idea
26:28 - Transformative Patient Stories and Evidence-Based Medicine
37:49 - Building Momentum and Overcoming Challenges
42:36 - Setting High Expectations and Team Dynamics
47:33 - Reflections on Selling Rupa Health