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.