Andrew Boos is the founder of Darwinian Ventures, a fractional sales advisory firm that builds go-to-market teams for early-stage B2B startups. He's also quietly investing in his own clients from profit, not a fund.

Before Darwinian, Andrew had a profitable exit at 24 from a startup that began as an ad exchange for China (yes, really), fell into post-exit depression nobody wanted to hear about, learned enterprise sales under a CRO with a $4.2 billion annual quota at a Sutter Hill incubation, blew his exit money trying to launch a quantitative hedge fund, and started freelancing to pay rent when law firms came knocking.

We talk about why a linear path to entrepreneurship is a privilege, what happens when your North Star disappears after an exit, how he built Darwinian from a solo 1099 gig into an embedded sales team that's worked with 100+ startups, and why he's now writing small checks into companies where he can see product-market fit before the founders do.

AI is moving so fast that it's hard to know what to pay attention to and what to tune out. In this episode, Michael Hoy (co-founder and CEO of Atlas) and I dig into what it feels like to build a company during the most disorienting moment in tech most of us have ever experienced.

Michael shares the full Atlas origin story, from winning Product Hunt's product of the day, week, and month, to the humbling realization that 1,200 users didn't translate into a single paying customer. We talk about why the startup advice machine creates more noise than clarity, how AI is shifting from exciting to existential, and why the founders who win are the ones who learn to trust their own signal over everyone else's opinions.

We also get into Michael's vision for where Atlas is headed: a trust layer for the coming agent-to-agent economy, and why that future might be closer than most people think.

Topics we cover:

• Why this month felt like AI truly woke up.
• Building 12 projects in a week and what that means for everyone else.
• The gap between Product Hunt traction and real product-market fit. Education-based marketing that leads with curiosity, not fear.
• Doing things that don't scale on purpose.
• Michael's advice to founders: trust what you're feeling and shut out the noise.

8 years in corporate sales. One birthday trip to Hawaii. Quit mid-vacation. Became Miss Hawaii 2025. Built a retreat business.

All in 24 months.

Nicole Miranda's timeline sounds impossible. It's not.

This episode is about what happens when you stop optimizing for other people's definitions of success and start trusting that you're on the right river.

We covered:

- The moment she quit her sales job

- Manifesting Miss Hawaii with Dr. Joe Dispenza

- Building Six Degree Soul (tours + retreats)

- Upcoming events in Oahu (August) and Bali (October)

- Why "follow your passion" misses the point

For anyone stuck in a "good" job that's killing them.

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

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.

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.

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

Ever wondered how creativity meets entrepreneurship? Dive into this conversation with Kyle Hudson and Will Taylor on "Zero to Umm..." where they chat about Will's journey from a physicist in a creative family to launching startups.

Get ready for some raw insights as Will reveals his experiences with a CV writing service, on-demand dry cleaning, and solving logistics with tech-driven solutions. They talk about the ups and downs of risk-taking, the grind of starting from scratch, and why failure is just another chapter in the entrepreneurial story.

Plus, hear about the tech behind Will's current venture, Workflow, where simplicity meets power in creative collaboration tools. The conversation covers the importance of validating ideas with real users and the charm of maintaining a small, effective team.

So if you're into creativity, startups, or just need a push to venture into the unknown, this episode's packed with relatable stories and valuable lessons. Don't miss out—catch the full episode now!

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

Summary

In this conversation, Cristina Cordova shares her journey through the startup ecosystem, detailing her experiences at various companies including Tapulus, Google, Stripe, Notion, and Linear. She discusses the importance of company culture, the role of partnerships in growth, and the significance of finding the right fit in a startup. Cristina emphasizes the value of working with strong founders and the need for startups to have a clear vision and product-market fit. Her insights provide valuable lessons for aspiring entrepreneurs and those looking to navigate the tech industry.

Chapters

00:00 The Journey into Startups
11:24 Finding the Right Fit in Tech
18:20 Building Relationships and Partnerships
23:59 Building Payment Infrastructure: The Early Days of Stripe
29:19 Transitioning to Notion: A Personal Journey
36:04 Joining Linear: The Right Fit and Company Culture
44:02 Key Insights for Startup Success: Lessons Learned

Episode Stack: https://stackl.ist/4atMQnD
(All the links)

Summary

In this episode I sit down with Perry "Dr. Octopus" Knoppert who shares his journey from homelessness to self-discovery, emphasizing the importance of nonlinear thinking and the power of asking for help.

He discusses the challenges of conforming to societal expectations and the liberation that comes from embracing one's uniqueness. The dialogue explores the concept of midlife crises as a catalyst for transformation and the significance of mindfulness and meditation in fostering creativity and clarity of thought.

We explore the importance of quieting the mind as a precursor to nonlinear thinking. They discuss the challenges of maintaining mindfulness in daily life, the significance of the octopus movement in promoting neurodiversity, and the need for a new form of leadership that allows for flexibility and creativity. The dialogue emphasizes breaking away from traditional norms and embracing new possibilities in personal and professional realms.

Chapters

00:00 Introduction and Energy Check
03:00 The Power of Asking for Help
06:06 Journey from Homelessness to Self-Discovery
08:56 The Impact of Nonlinear Thinking
11:56 Breaking Free from Linear Expectations
15:13 Embracing the Weird and Nonconformity
18:05 Midlife Crisis and Transformation
20:59 The Beauty of Nonlinear Thinking
23:54 Meditation and Mindfulness in Nonlinear Thinking
30:06 Quieting the Mind: The First Step to Nonlinear Thinking
40:05 Transitioning into Mindfulness: Finding Moments of Peace
42:04 The Octopus Movement: A Journey of Nonlinear Thinking
46:03 Redefining Leadership: The Nonlinear Manager
54:00 Breaking Traditional Norms: Embracing New Possibilities

TLDR; About Ruky

• Founder and Managing Attorney of Firm for the Culture
• LinkedIn: https://www.linkedin.com/in/rukayatutijani 
• Instagram: https://www.instagram.com/firmfortheculture
• Firm for the Culture Events: https://bit.ly/m/FFTC-Events

Summary

In this conversation, Rukayatu ("Ruky") Tijani shares her journey from a traditional legal career to founding Firm for the Culture, a company focused on making intellectual property law more accessible for social entrepreneurs. She discusses the challenges she faced in her early career, the importance of community and coaching, and her vision for the future of her firm, emphasizing the need for holistic support for her clients.

Takeaways

• Ruky transitioned from a traditional legal career to entrepreneurship.
• She faced challenges reconciling her identity in corporate America.
• The importance of community and support in entrepreneurship is crucial.
• Ruky aims to make IP law more accessible to entrepreneurs.
• She emphasizes the value of coaching and mentorship in her journey.
• Building a brand that resonates with clients is essential.
• Ruky's firm focuses on social impact and supporting founders.
• She believes in the power of connection among entrepreneurs.
• Ruky's journey highlights the importance of self-trust and resilience.
• Future plans include expanding services and creating community initiatives.

Chapters

00:00 - Introduction and Personal Updates
06:03 - Early Career Journey and Law School Experience
11:04 - Transition to Silicon Valley and IP Law
17:04 - The Decision to Pursue Entrepreneurship
24:00 - Navigating the Challenges of Big Law
29:45 - Finding Perspective and Building a New Path
35:31 - Transitioning from Law to Entrepreneurship
39:24 - Building Confidence and Finding Clients
41:06 - Learning the Business of Law
46:11 - Navigating the Challenges of Entrepreneurship
52:22 - Market Research and Ideal Client Avatar
56:28 - Future Plans for Firm for the Culture

Summary

In this conversation, Kyle Hudson and Denzil Eden discuss the journey of entrepreneurship, focusing on Denzil's experiences from his early coding days to founding Smarty. They explore the challenges of transitioning from a corporate career to startup life, the importance of validating ideas through sales, and the lessons learned along the way. Denzil shares insights on navigating imposter syndrome, the significance of customer feedback, and the evolving landscape of startup funding. The discussion culminates in a vision for the future of Smarty and the ongoing journey of growth and innovation.

Takeaways

• Diving into the zero to one journey is unique for everyone.
• Early coding experiences can ignite a lifelong passion for technology.
• Imposter syndrome is common among founders; it's important to recognize it.
• Sales focus is crucial in the early stages of a startup.
• Building a product without customer validation can lead to pitfalls.
• Finding the right customer profile is essential for growth.
• Your gut instinct improves with experience and exposure to uncertainty.
• It's important to balance intuition with external feedback.
• The journey from zero to one is filled with unknowns and challenges.
• Having a clear vision can guide a startup through its early stages.

Chapters

00:00 - Introduction and Background
00:55 - From Coding Enthusiast to Startup Founder
04:55 - The Journey from Microsoft to Academia
08:58 - The Vision for Smarty: A Conversational Productivity Operating System
12:47 - The Value of Being a Generalist as a Founder and CEO
16:08 - Challenges and Lessons Learned in Starting a Company
20:04 - The Challenges of Being a Solo Founder
23:13 - The Importance of Seeking the Right Advice
25:38 - From Product Building to Customer Validation
28:33 - Balancing Intuition, Data, and External Input
37:29 - The Journey of a Startup: Learning and Adaptation
44:50 - Passion and Mission: Sustaining Motivation in the Long Run

Episode Stack: https://stackl.ist/41VfkDh

Kyle sits down with the inspiring young entrepreneur, Erifili Gounari. Starting as a digital-savvy Gen Z, Erifili turned her passion for building online communities into a groundbreaking venture—a social media agency called the Z Link, aimed at bridging the gap between brands and Gen Z consumers.

 At just 19, she navigated the challenges of university, part-time jobs, and launching a business, ultimately making it onto the Forbes 30 under 30 list. Kyle and Erifili dive into the origin story of the Z Link, the significance of authenticity in marketing to Gen Z, and how content creation and entrepreneurial drive propelled Erifili's journey from a hobbyist to a successful founder. 

Whether you're a budding entrepreneur or just fascinated by the dynamics of Gen Z marketing, this conversation is packed with insightful perspectives and actionable advice. Tune in for an engaging chat that explores the intersection of creativity, innovation, and the ever-evolving landscape of digital marketing.

What if you could transform the emotional turbulence of entrepreneurship into a journey of growth and opportunity? Join us as we explore the profound intersection of personal and professional development with our insightful guest. We uncover the emotional rollercoaster faced by entrepreneurs, especially during transitional phases, and the importance of a creative mindset to unlock business growth. Through personal anecdotes and expert insights, we reveal how internal belief systems and external support frameworks, including mentors and coaches, are vital in maintaining confidence and steering clear of a survival mindset.

Our episode delves into the special challenges faced by neurodivergent entrepreneurs or those with ADHD, highlighting the potential advantages of a unified support system. We discuss the sometimes paradoxical roles of therapy and coaching in building a resilient entrepreneurial mindset. Listen as we debate the benefits of integrating these approaches to address both personal challenges and business strategies effectively. By weaving together relatable experiences and critical insights, we emphasize that personal growth is not just a side benefit, but a core component of entrepreneurial success.

Transitioning from traditional employment to the unpredictable world of entrepreneurship is no small feat, and our guest's journey from firefighter to business leader illustrates this vividly. Faced with financial insecurities and the fear of failure, they found inspiration and clarity in unexpected places, such as a Tony Robbins event that became a catalyst for change. We conclude by celebrating the passionate spirit and dynamic life of entrepreneurship, acknowledging both its pressures and its unparalleled joys. Whether you're just starting out or seeking to enhance your entrepreneurial path, this episode is packed with wisdom and inspiration to guide your journey.

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.

In this episode, I have the pleasure of interviewing Tony Clemendor, who was not only my coach but also a fantastic mentor. As a fellow neurodivergent, Tony brings a unique perspective to entrepreneurship, sharing his journey from bootstrapping a startup to scaling it to $80 million in revenue. 

We discuss his insights on the new economy, the simplicity of entrepreneurship, and the importance of adaptation. Tony's creative approach to overcoming challenges and his belief that every first idea is just a draft make this conversation both inspiring and practical for aspiring entrepreneurs. 

You're going to love the insights uncovered in this episode. 

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

Summary

In this episode, Grady Teske, founder of Rising Tides, shares his journey from helping multinational manufacturers to founding Rising Tides, a company focused on building distribution and marketing strategies. Grady discusses the importance of understanding one's core function and audience, and how aligning these elements can lead to success. He emphasizes the value of authenticity and human connection in business, and how automation and AI can enhance these relationships. Grady also reflects on the lessons learned from his entrepreneurial journey, offering insights for aspiring founders on building effective systems and processes. Join Grady and Kyle Hudson as they explore the intricacies of scaling businesses and the power of distribution in today's market.

Chapters

00:00 - Introduction and Setting the Scene
01:36 - The Importance of Authenticity in Media
04:13 - Grady's Journey to Entrepreneurship
10:19 - Building Rising Tides: The Evolution of a Business
15:29 - The Role of Distribution in Business Success
22:07 - Automation and the Future of Marketing
28:15 - Navigating Growth and Scaling Challenges
34:15 - The Power of Community and Connection
40:08 - Advice for Aspiring Entrepreneurs
45:57 - Looking Ahead: Future Plans for Rising Tides

What is this? What does the title of this podcast even mean? What is a Stacklist? 

All these questions, and more, will be answered in this very short five minute introduction. I look forward to a long and wonderful journey of interviewing founders and entrepreneurs to understand how they started and grew a company from idea into reality. 

*Episode Stack:* https://stackl.ist/43dFyTt

🚀 From Zero to ClickUp: Chris Cunningham's Startup Journey

In this incredible episode, Chris Cunningham shares the fascinating story of how he and his co-founder Zeb Evans built ClickUp from the ground up! 

*Key highlights:*

📍 Early Beginnings:
- Started by managing a rapper in college
- Built an internal project management tool called "Mission Control Center"
- Pivoted from a social media app after Snapchat copied their concept

💡 Startup Secrets:
- Stayed scrappy and looked for unique opportunities
- Weren't afraid to pivot and ignore traditional advice
- Focused on shipping fast and improving continuously

🌟 Breakthrough Moments:
- First customer from Accenture in 2016
- Acquired customers from a competing app shutting down
- Closed deals with Home Depot and Randstad

🎯 Future Vision:
- Aiming to go public
- Expanding features with AI
-Committed to building an exceptional product

Chris's advice? Be scrappy, focus on your product, and always be looking for opportunities!
#Startup #SaaS #Entrepreneurship #ClickUp

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!

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!

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

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.

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

Summary

In this episode, Simon shares his unconventional journey as an entrepreneur, starting from his diverse upbringing in Peru, Australia, and Spain to launching multiple businesses. He discusses the challenges and learning experiences that shaped his approach to building companies, including his first venture, an app development service called Get Appy.

Simon dives into the early stages of his latest project, Vera, which aims to simplify administrative tasks for small and medium-sized businesses by organizing and sharing information more efficiently. He explains the importance of understanding customer needs and adapting to market demands, emphasizing that constraints can lead to innovative solutions.

You’ll gain insights into the realities of starting a business, the significance of having a clear vision, and the evolving nature of product-market fit. Simon also touches on the role of funding in business growth and the strategies he employs to navigate the entrepreneurial landscape. This conversation offers practical advice for anyone interested in entrepreneurship or looking to streamline their business operations.

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

Episode Stack: https://stackl.ist/3W1QAGR

I had THE BEST conversation with Caroline Clark, Co-Founder and CEO of Arcade, about the journey from zero to building a product that's changing how teams create interactive demos. 

We talked about her path from consulting to product marketing at companies like Atlassian, and what led her to start Arcade. What stood out to me was her honesty about the hard parts of building a company. The burnout, the failed launches, the moments at 4:30 AM questioning everything.

Some things that stuck with me:

• Why the best market isn't always the obvious one
• The real cost of being on the hook for marketing output (and why she built Arcade)
• How a "failed" product launch became their most successful enterprise offering
• The importance of staying close to what brings you joy when building

If you're in the early stages of building something, Caroline's advice about being passionate and not getting too attached to one-off moments is worth hearing. She's built up what she calls a "lower bar for embarrassment" over time, which feels like an underrated founder skill.

Chapters

00:46 - Introduction and Background
11:52 - Early Career and Transition to Marketing
25:21 - Joining Atlassian and Learning from Failures
34:12 - The Importance of Market Fit
45:44 - Venture Capital Insights and Growth Mindset
56:30 - Building Arcade: Challenges and Successes
1:09:18 - Future of Arcade and AI Investments
1:22:14 - Advice for Aspiring Entrepreneurs

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. 

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

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

Summary

In this episode of our podcast, I had the pleasure of speaking with Vicki, the founder of Joy of Mom, a vibrant community dedicated to supporting mothers through the ups and downs of parenting. Our conversation delved into the evolution of her journey, from her early career in sales and advertising to her passion for creating a safe space for moms to connect and share their experiences.

We began by discussing the intimate and personal nature of the connections formed within communities like Joy of Mom. Vicki shared her insights on the importance of authenticity in a world often dominated by curated perfection. She emphasized that her approach has always been about being real and relatable, which resonates deeply with her audience.

As we explored her background, Vicki recounted her early career in television and radio, her transition into writing children's books, and the challenges she faced while developing her first software product aimed at validating children's feelings. This journey was marked by a lack of resources and experience, yet fueled by sheer determination and a desire to make a difference.

A pivotal moment in her journey came when she realized the need for mothers to have a platform where they could share recommendations and support one another. This led to the organic growth of Joy of Mom, where Vicki engaged directly with her audience, responding to their needs and fostering a sense of community. We discussed the challenges of maintaining that authenticity while navigating the complexities of social media and the pressures of commercialization.

Throughout our conversation, Vicki highlighted the significance of shared experiences and the power of connection. She shared anecdotes about her interactions with moms who felt seen and heard through her content, reinforcing the idea that community is built on trust and genuine relationships.

As we looked to the future, Vicki expressed her excitement about expanding Joy of Mom into new areas, including micro-groups and curated resources that address the specific needs of mothers today. We touched on the importance of creating a safe and nourishing environment for moms to thrive, especially in a world filled with noise and distractions.

This episode is a heartfelt exploration of motherhood, community, and the journey of building something meaningful from the ground up. Vicki's story is a testament to the power of authenticity and the impact of connecting with others on a shared journey. Join us as we celebrate the beauty of imperfection and the strength found in community.

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.

Meet Teja Yenamandra
Founder & CEO of Gun.io ( @gunio )

• Gun.io -  World-class engineering talent, on tap. 🤠 - http://gun.io
• Gun.io - X - https://x.com/gundotio
• Teja - LinkedIn - https://www.linkedin.com/in/tejayenamandra

Summary

Teja and Kyle discuss the early days of building a startup and the mindset required to be successful. They talk about the challenges of starting a business with limited resources and the need to be scrappy and resourceful. 

Teja shares his experience of burning through savings and taking on personal debt to fund the business. They also discuss the importance of having a strong support system and a team that can cover different areas of the business. 

Despite the challenges and doubts that arise along the way, Teja emphasizes the need to stay focused on the long-term vision and make decisions based on the potential for success rather than the probabilistic likelihood of failure. Teja reflects on his journey as the CEO of Gun.io and shares his vision for the future of the company. He discusses the importance of building a long-term business and setting it up for success beyond his own involvement. 

Teja also emphasizes the value of meeting with people and listening to their feedback to continuously improve the product. He envisions Gun.io as a modular platform that can support various hiring needs and provide value to both companies and developers. Overall, Teja's goal is to create a company that lasts for the next 90 years.

Episode Stack: https://stackl.ist/4c0BOHv 

Today, we have a riveting conversation with Andy Budd, a seasoned design leader and former founder who takes us through the exciting trajectory of his life. 

From learning HTML in a hostel in Singapore to pioneering one of the first UX agencies in the UK, Andy shares his insights on embracing self-reliance, breaking the mold, and the transformative power of design in building brilliant products. 

We also delve into his experience with venture capital, where he helps other entrepreneurs navigate their journeys. Join host Kyle Hudson as he unpacks the elements of risk, curiosity, and problem-solving in entrepreneurship with Andy Budd, and discover how you can tap into the design world to inspire your own business journey. 

Whether you're a current founder or someone just starting out, this episode has something for everyone who aspires to grow and innovate in today's fast-paced environment.

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

Summary

In this conversation, Kyle Hudson and Birute discuss the journey of entrepreneurship, focusing on the creation and growth of beCreatives. They explore the challenges of balancing family life with business, the importance of personal growth, and the evolution of their company in response to changing market dynamics, including the rise of AI. Birute shares her personal story of resilience, the support of her business partner, and the lessons learned along the way. The discussion emphasizes the significance of creativity, adaptability, and the human touch in the digital age.

Takeaways

• Birute's entrepreneurial journey began as an immigrant in the U.S.
• The importance of creating a work-life balance for family.
• AI can enhance video editing but won't replace the human touch.
• Building a business requires adaptability and resilience.
• The early days of beCreatives were marked by experimentation.
• Having a supportive business partner is crucial during tough times.
• Creative processes should be approached with a flowy mindset.
• Scaling a business requires establishing effective processes.
• Personal challenges can lead to significant growth and change.
• Embracing change and innovation is essential for future success.

Chapters

00:00 - Navigating Technical Difficulties and Family Life
10:49 - The Birth of Be Creatives
19:26 - The Journey to Entrepreneurship
27:53 - Scaling Up: From Editing to Team Building
39:19 - Overcoming Personal Challenges
46:25 - Embracing AI and Future Innovations

Episode Stack: https://stackl.ist/41vbWPM

In this conversation, Claude Silver, the Chief Heart Officer at VaynerX, discusses her journey and the importance of empathy in the workplace. She emphasizes the need for self-awareness, understanding emotions, and creating a culture that values people. Silver shares insights on hiring practices, the transition to her current role, and the significance of communication in a remote work environment. She highlights the importance of building a people-centric organization and the future goals she aims to achieve in her role.

Takeaways

• Empathy is a superpower in leadership.
• Self-awareness is crucial for effective communication.
• Creating a culture of safety allows for open expression.
• Hiring should focus on culture addition, not just fit.
• Understanding employees' personal lives enhances workplace culture.
• Communication must be intentional and consistent.
• Celebrating small wins fosters a positive environment.
• Emotional intelligence is key in navigating workplace dynamics.
• Building relationships is essential for a thriving organization.
• The role of Chief Heart Officer is about serving people. 

Summary

Mike Preuss and Kyle covers topics such as their diverse range of hobbies, the early stages of building Visible, the challenges and pivots they faced, and finding balance as a founder. They discuss the importance of trusting your gut, the struggle of market sizing and messaging, and the shift from selling to investors to selling to founders. They also touch on the growth of Visible and the balance between work and personal life. The conversation concludes with a discussion on remote teams and maintaining culture. 

Mike discusses the challenges and strategies of building a remote-only business. He emphasizes the importance of off-sites and intentional communication in creating a strong remote culture. Preuss also shares his key takeaways for founders, including trusting your gut, moving faster, not being afraid to burn cash, and charging more. The conversation covers topics such as pricing and packaging, growth marketing strategies, and the future plans for Visible.

Takeaways

• Trusting your gut is important as a founder, even when faced with doubt and self-doubt.
• Market sizing and messaging can be challenging, and it's important to pivot and adapt to find the right customer fit.
• Visible experienced growth and success by focusing on selling to founders and providing a product that meets their needs.
• Finding balance between work and personal life is an ongoing process, especially as a founder.
• Remote teams can maintain culture and collaboration through intentional efforts and a distributed work model. Building a remote-only business requires intentional communication and a strong remote culture.
• Trust your gut, move faster, and don't be afraid to burn cash.
• Charge more for your product or service and be open to testing and raising prices.
• Focus on one or two key marketing channels that work best for your business.
• Create repeatability and predictability in your sales process.
• The journey from zero to one is the most rewarding and exciting part of building a business.