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/3YXM0uc
(All links relating to this episode 🎁)

Overview
I loved making this episode with Ben and it feels like we came from similar places and similar mindsets as it relates to computers, learning, and business.

Ben, the co-founder of Contra, is revolutionizing traditional employment norms.

Growing up in a small town in South Carolina, Ben's curiosity led him from a young boy fascinated by the hum of a computer to an innovative entrepreneur in the tech industry. Together, we delve into the genesis of Contra and the initial skepticism Ben faced, as well as why traditional professional norms such as resumes and suits persist, despite technology offering creative professionals new opportunities.

We further explore Ben's personal journey, from his self-taught skills in music production to his entrepreneurial ventures. Through anecdotes, we discuss the transformative power of technology in shaping careers, and how platforms like Contra are enabling creative professionals to redefine their paths. We also delve into the value of contract portfolios in demonstrating one's capabilities, bypassing traditional interview limitations.

As we delve deeper into our conversation, we touch upon the changing landscape of learning and career-building in the digital age, highlighting the shift from traditional paths to self-taught and creative avenues. We examine the impact of new platforms born out of frustrations with existing systems, envisioning a future where networks seamlessly integrate payments, contracts, and identity verification without commission fees.

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Episode Summary

In this podcast episode, Kyle interviews Sarah, the Founder of Mys Tyler, an innovative fashion platform. Transitioning from the telecommunications industry to fashion, Sarah discusses her journey from running sales and marketing for a telecommunications company to becoming an entrepreneur.

She speaks about her first business, Doodad, a telecommunications venture that morphed from a $50,000 pilot project into a million-dollar venture, but eventually had to shut down. She shares her experience of dealing with the closure of Doodad and how it led to the birth of Mys Tyler. Sarah was inspired to start Mys Tyler after struggling with personal fashion choices and wanting to balance comfort with style.

The platform matches users with creators of similar body types, offering personalized style inspiration. She discusses the innovative strategies used to overcome the cold start problem, like using celebrity data and creating engaging quizzes. Sarah shares her experiences with the unpredictable and challenging process of fundraising, the emotional experience of notifying customers and suppliers about Doodad's closure with just 48 hours' notice, and the unexpected positive feedback received despite the abrupt closure.

Sarah then delves into the journey of launching Mys Tyler, leveraging affiliate marketing and influencer trends. She discusses the creation of a unique business model that resulted in the successful launch of Mys Tyler.Throughout the interview, Sarah emphasizes the importance of perseverance, adaptability, and a solid network for entrepreneurs. She also highlights the need for self-care amidst the excitement and challenges of startup life.

Highlights

(00:38) From Zero to One (137 Seconds)
(05:55) Doodad (61 Seconds)
(12:03) Discovering Entrepreneurial Ideas (108 Seconds)
(22:56) Navigating the Startup Numbers Game (47 Seconds)
(26:40) Discovery of Entrepreneurial Passion (63 Seconds)
(30:10) Celebrity Body Double Algorithm App (132 Seconds)
(35:20) Evolution of Celebrity-Free Social App (70 Seconds)
(38:16) Navigating Fundraising Challenges as a Founder (109 Seconds)
(44:12) Mark Zuckerberg's Inspirational Startup Journey (88 Seconds)
(49:24) Startup Support and Community Growth (81 Seconds)

Quotes"I actually can execute and I do have good ideas and once you know how to execute, it becomes very hard to not want to execute when you see a really big opportunity."

"I remember having conversations with a friend and I was, like you know, printing out business card and I'm like am would CEO on there, like I felt like such a fraudster."

"But it was actually really surprising to me that, like, a lot of people don't actually have ideas and you know there was a bunch."

"I too, I too find funding fundraising a very difficult experience. I, you know it is really tough and that was not like."

"I've had the idea for a very long time and it wasn't until 2020 that I basically was like I'd had six years of pent up entrepreneurial energy and I was like I can't, I can't not be doing this anymore."

Chapters

(00:00) - Entrepreneurship Journey
(13:51) - Fashion Innovation for Women's Social Media
(16:45) - Navigating the Entrepreneurial Fundraising Journey
(27:43) - Entrepreneurial Validation and Platform Development
(38:26) - Founder's Struggle With Fundraising Mindset
(45:48) - Entrepreneurial Journey Reflection and Growth

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Wrapping up the first season of Zero to Umm, I’m taking a moment to look back on the year—what worked, what didn’t, and some of the biggest lessons along the way. Just a casual reflection to close things out.

Thanks for listening and being part of it all!

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Meet Dani Grant - Co-founder & CEO of Jam (jam.dev)

• Jam - https://jam.dev
  • 1 click to capture a perfect bug report. Trusted by 32 of the Fortune 100, and 150K happy users. 🍓
• Jam on X - @jamdotdev
• Jam on Instagram - @jamdotdev
• Dani - LinkedIn

Summary

In this conversation, Kyle Hudson and Dani Grant discuss the journey of building their respective companies, focusing on the importance of community, authenticity, and transparency in tech. They share insights on the early challenges faced while developing their products, the significance of fundraising, and the evolving nature of user engagement. The discussion highlights the value of storytelling and personal connections in the startup ecosystem. In this conversation, Kyle Hudson and Dani Grant discuss the journey of building a startup, emphasizing the importance of networking, patient capital, and the challenges of achieving product-market fit. They explore the dynamics of team building, the value of contracting before hiring, and the significance of maintaining a positive company culture in a remote work environment. The discussion highlights the need for resilience and adaptability in the face of uncertainty, as well as the goal of creating a human-centric company that fosters genuine connections and joy in the workplace.

Takeaways

• There's an energy in what you are building.
• Building in public creates a sense of community.
• Transparency in tech fosters trust and authenticity.
• Early fundraising can be crucial for startup success.
• Iterating on product ideas is essential for finding market fit.
• User engagement is key to sustaining a product's success.
• Listening to user feedback can guide product development.
• Storytelling is a powerful tool for founders.
• Building a strong company culture is vital.
• Networking and personal connections can open doors for fundraising. Networking is about connecting with like-minded individuals.
• Patient capital can make a significant difference in a startup's journey.
• Achieving product-market fit often takes longer than expected.
• Embracing uncertainty is crucial for startups.
• Building a drama-free team enhances productivity and morale.
• Contracting can help identify the right team members before hiring.
• The future of Jam includes expanding its product offerings.
• Company culture is reinforced through positive interactions and shared experiences.
• Creating a human-centric company fosters genuine connections.
• Joyful moments in the workplace enhance team dynamics.

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This episode highlights the inspiring journey of Alex Lotier, Co-Founder of Culture Kicks.

From their initial struggles to building a brand that resonates with millions. Through discussions on mindset, partnerships, and community engagement, they share valuable lessons for aspiring entrepreneurs.

• Emphasizing the importance of a positive mindset
• The significance of partnerships in entrepreneurship
• Navigating the “zero to one” concept in building a brand
• The evolution of audience relationships and community building
• Future growth plans and commitment to innovation
• Overcoming self-doubt and embracing risks in business