Fundraising: Demystified! True Stories Direct From Founders

In this episode of Fundraising Demystified, I sit down with Ben Chiang, the former head of Uber China and founder of Forma (acquired by Snap- yes, from Snapchat), to unpack his journey through hypergrowth, high-stakes fundraising, and strategic exits. Ben shares the realities behind building in chaotic markets, the truth about investor dynamics post-exit, and how founders can stay sane while chasing scale.

We dive into the unde...

60 pitches in 90 days. A Series B term sheet that collapsed. A $15M valuation hit, and she still came out on top.

In this episode, Jennifer Henderson, founder of Colorado-based HR tech startup Tilt, breaks down exactly what it took to raise over $30 million in venture capital while balancing motherhood, market crashes, and investor whiplash.

Jen shares how Tilt was born out of personal trauma, why she built a leave management...

This week, I talk to Travis Steffen, who has built and sold eight companies. He’s raised over $100M and driven more than $200M in exits.

In this episode, we delve into what actually drives startup growth and what quietly undermines it. We also get into how one bad exit almost wrecked him, and what he learned from losing years and seven figures because of one avoidable mistake.

If you're a founder, operator, or even just t...

Most founders dream of a life-changing exit. But few actually prepare for it, until it’s too late.

In this episode of Fundraising Demystified, I sit down with John Rood, an exited founder who scaled a tutoring side hustle into a global edtech business, and sold it for over eight figures to private equity.John also shares the story behind his book Beyond the Exit and why post-exit life is often not what you think it will be.

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What happens when you raise $2.7M... then realize you never want to raise again?

Jennifer Tsai, founder and CEO of Shoott.com, built a profitable photography marketplace from the ground up; surviving death threats from creatives, a brutal CAC spike post-iOS14, and the chaos of marketplace economics. In this episode of Fundraising Demystified, we dive into how she scaled to $10M in revenue, hit breakeven, and is now facing...

This week on Fundraising Demystified, I sat down with David Connors, founder of The Swarm, a Go-To-Network platform transforming how founders and investors connect- think LinkedIn but for companies.

David shares how he used The Swarm to raise capital for his own startup, how the product helps other founders close rounds, and what he learned from working at Sequoia.

Raising capital?

Get a list of vetted VCs for FREE here: https://web.t...

In this episode, Jess Loren, founder and CEO of Global Objects, shares her journey on raising capital as a female founder, including turning down a $20M offer and building her business using digital twins technology.

Jess dives into how she's building a tech company rooted in culture, purpose, and innovation, while navigating the fundraising landscape as a female CEO. We talk about generative AI in media, managing a startup ...

Startup Advisors can make or break your growth. In this episode, Barry Stamos of Supernova shares how to build a world-class startup advisory board, manage relationships, and scale successfully.

With real-world lessons from the Tuft & Needle journey and his advisory platform Supernova, Barry dives deep into sourcing the right advisors, setting success metrics, avoiding red flags, and aligning compensation with performance.

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This week, I host IPO market expert Peter Goldstein, who talks about the best time to IPO, how to position for strong IPO performance, what true IPO readiness looks like, and how companies are being valued in 2025.

If you're a founder eyeing the public markets, this is your roadmap. We dive into shifting investor sentiment, the surge in the secondary market, and strategic insights on when to go public, build public company c...

JC Glancy, co-founder of ZenBusiness, shares his remarkable unicorn startup journey, from nearly drowning in credit card debt to building a billion-dollar startup. In a bold and rare move, he gave up the CEO title early on but still led the company to raise a $200M Series C and dominate the legal tech space.

This episode dives deep into startup realities: raising venture capital, overcoming failure, building an unbeatable team, outm...

In this episode, Gil Eyal of Stardust Ventures shares expert insights on celebrity marketing and influencer deals for startups. Learn how to pitch your startup to influencers, find the best platforms to connect, and structure celebrity deals, all without breaking the bank. Plus, discover the biggest mistakes startups make with influencer marketing and how to avoid them.

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Raising cap...

In this episode, I sit down with Adam Spector, CEO of Chore, to break down founder mindset, startup operations, and how to make a startup successful. Adam shares what separates successful startup founders from those who fail, covering topics like founder time management, startup productivity, outsourcing, and the best outsourcing tools for startups. We also dive into the reality of starting a business, common founder mistakes, and ...

How do you identify and capitalize on the biggest upcoming trends?

Katelyn Donnelly, GP of Avalanche Ventures, unveils her unique investment strategy focusing on "avalanches" – inevitable market trends driven by societal and technological shifts. In this episode, Katelyn shares her insights on what VCs look for in early-stage startups, emphasizing the importance of founders building their life's work and understanding the nuances of...

Wondering what VCs look for in early-stage startups? In this episode, Dave Lambert, Managing Partner at Right Side Capital Management, shares insights on how to get funding for a tech startup, the importance of technical co-founders, and how to raise pre-seed capital while keeping control of your business.

With over 2,000 investments, Dave reveals the fundraising strategies that work in 2025, common mistakes founders make, and w...

Jeremy Parker, co-founder of Swag.com discusses his incredible journey of building a successful swag business from scratch and ultimately selling it to Custom Ink. Jeremy shares valuable insights on raising capital, identifying market opportunities, and navigating the acquisition process.

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Raising capital? 

Get a list of vetted VCs for FREE here: 

https://web.thunder.vc/list-of-in...

AI for Business Efficiency is reshaping how companies operate, and in this episode, Jon Tucker, founder of HelpFlow, shares how AI is transforming customer service, workflow automation, and decision-making. We dive into Evaluating AI Performance, optimizing operations, and leveraging AI to scale businesses while staying competitive.

Jon reveals how AI reduces workforce needs, enhances productivity, and even impacts venture capit...

Not all startups should chase VC money. Some should bootstrap, others should take on debt, and a few are primed for private equity. So how do you know which path is right for you?

In this episode,Jason Kirby breaks down theFundraising Quadrants—a framework that helps founders identify where they stand in their startup journey and what type of capital makes the most sense for them. Whether you’re running an AI startup, a SaaS com...

Would you rather grind for years bootstrapping, take VC money with strings attached, or sell and move on? That’s the exact crossroads Laurits Just faced as the co-founder of BitsForDigits.

In this episode, Laurits breaks down how he built and sold his startup, a marketplace for partial business acquisitions, and why he ultimately chose to exit instead of raising venture capital. He shares the highs and lows of bootstrapping,...

Penelope Hope, founder of Rebel Energy, shares her journey of building a renewable energy company from scratch with just £1.5 million raised, scaling it to £100 million in revenue in record time. Rebel Energy's mission to alleviate fuel poverty while delivering renewable energy has set it apart as an innovative force in the UK energy sector.