Episódios
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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?
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Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast
Sign up to get 70% off the Swarm: theswarm.com/thunder
Here’s what you’re in for:
00:42 - Who is David Connors and what is The Swarm?02:08 - How working at Sequoia birthed The Swarm
05:32 - Raising The Swarm’s $2M pre-seed round solo (and why it was capped)
11:37 - Raising a $4M seed and scaling a building a winning team
14:31 - How to find investors and pick the right ones for follow-on funding
18:52 - Getting warm intros for investor outreach in minutes
22:28 - The best kind of warm intros ranked
25:43 - Why Swarm raised an extension round
29:10 - The shift from SaaS to data, 10xing revenue and getting Hubspot Ventures to invest
32:40 - Vibe coding and AI tools that support The Swarm’s scale
35:02 - Top tips for personal branding that boosted growth
Check out the pre-seed investment memo for The Swarm here: https://docs.google.com/document/d/1wzo0PxFCyNgaD627-e2q2wefV0LUk4DJjnEr3R4b07k/edit?tab=t.0ABOUT DAVID CONNORS
David Connors is the founder of The Swarm, a Go-to Network platform that helps startups access warm intros to capital, talent, and strategic partners. A second-time founder with deep experience in startup M&A, David previously built a company acquired by Levels, a Sequoia-backed health tech firm. With a background in enterprise sales and operations, he built The Swarm to solve one of the hardest problems founders face: getting in front of the right people without wasting time on cold outreach.
Connect with David via:LinkedIn: https://www.linkedin.com/in/connorsdavidWebsite: http://theswarm.com/
ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thanks for tuning in! We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
#startupfunding #venturecapital #theswarm #founderstories #fundraisingdemystified #saas #data #investoroutreach
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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 as a mom, building a tech community, and how to use AI to boost productivity.
A great story about leadership, innovation, and startup resilience.
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Raising capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode83&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode83&utm_id=FundraisingDemystifiedPodcast
Here's what you're in for:
00:00 - Intro
00:35 – Raising Capital as a Female Founder: Intro to Jess Loren & Global Objects
03:06 – Building a Tech Community in LA
06:05 – Balancing Life as a Female CEO
08:42 – Digital Twins Technology for Culture & Innovation
13:16 – Using AI to Boost Productivity in Creative Industries
16:34 – Generative AI in Media & Entertainment
22:18 – Jess Loren’s Journey: From 2X Exit Founder to Building Global Objects
25:47 – Funding Strategies & Investor Alignment
28:16 – Global Objects' Mission and Growth Plan
31:30 – Startup Leadership as a Female CEO
34:05 – Jess Loren on Persistence, Boards & Building Visibility
ABOUT JESS LOREN
Jess Loren is a 2X exited founder and the CEO of Global Objects, a cutting-edge startup at the intersection of digital twins technology, cultural preservation, and generative AI. With a background in community building, immersive experiences, and Web3 innovation, Jess is known for her bold leadership, fundraising acumen, and vision for reshaping how we digitally capture and interact with the world. Her journey includes turning down a $20M term sheet to stay mission-aligned, proving that purpose and persistence can coexist at scale.
You can reach out to Jess through:
LinkedIn: https://www.linkedin.com/in/jessloren/
Global Objects' LinkedIn: https://www.linkedin.com/company/globalobjects/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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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Raising capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode82&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode82&utm_id=FundraisingDemystifiedPodcast
Here's what you're in for:
00:00 – Introduction
00:08 – Meet Barry Stamos: Founder of Supernova
00:43 – Barry’s startup journey and lessons from past exits
03:10 – Why startup advisors and mentors are critical
03:29 – Finding and managing startup advisors effectively
05:29 – Startup advisor success story: learning from experience
08:56 – The right time for early stage startup support
12:26 – Tuft & Needle case study: startup advisor success story
16:04 – The real role of startup advisors in startup growth
20:33 – Managing advisor relationships for success
21:27 – How to compensate startup advisors effectively
23:53 – How to find startup advisors and sourcing advisors for startups
25:55 – Making aggressive advisor requests
29:16 – Startup advisor horror stories and startup advisor red flags
33:05 – Introducing Supernova: the startup advisor platform
35:44 – How Supernova matches advisors with founders
37:51 – Advice for founders seeking advisors and building a startup advisory board
40:00 – How to connect with Barry Stamos and Supernova
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ABOUT BARRY STAMOS
Barry Stamos is a 3x exited founder, startup advisor, and CEO of Supernova—a platform that connects high-growth startups with a curated network of successfully exited founders. With a track record that includes advising breakout companies like Tuft & Needle, Barry specializes in helping startups scale smarter through strategic advisory boards, hands-on mentorship, and performance-driven advisor relationships.
You can reach out to Barry through:
LinkedIn: https://www.linkedin.com/in/bstamos/
Supernova's Website: https://1supernova.com/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 credibility, and leverage equity in IPOs to your advantage.
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Raising capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode81&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode81&utm_id=FundraisingDemystifiedPodcast
Here's what you're in for:
00:00 – The 2025 IPO market
02:15 – Investor sentiment in the current IPO climate
04:40 – Why IPO timing is critical: the best time to IPO
07:25 – IPO valuation expectations and market sensitivities
10:05 – IPO readiness checklist for founders
12:50 – What happens after IPO: risks and surprises
16:15 – IPO performance in 2024 vs 2025
19:30 – Market cap requirements for IPO explained
22:10 – How equity in IPO impacts control and growth
25:20 – Benefits of going public beyond capital
28:05 – Public company credibility and strategic advantages
31:15 – The rise of the secondary market and investor access
34:30 – Private stock trading trends and access to liquidity
37:20 – When should you go public?
40:10 – Employee stock incentive strategies in public companies
43:30 – Parting shot from Peter Goldstein
ABOUT PETER GOLDSTEIN
Peter Goldstein is a leading expert in the IPO market, founder of Exchange Listing LLC, and author of The Entrepreneur’s IPO. With decades of experience guiding small and micro-cap companies through public offerings, Peter is known for helping founders navigate the complexities of going public. His deep understanding of IPO readiness, valuation, and investor strategy makes him one of the most trusted voices in the space.
You can reach out to Peter through:
LinkedIn: https://www.linkedin.com/in/peter-goldstein-exchangelisting/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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, outmaneuvering big competitors like LegalZoom, and scaling ZenBusiness through SEO, affiliate marketing, and obsessive customer focus.
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Raising capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode80&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode80&utm_id=FundraisingDemystifiedPodcast
Here's what you're in for:
00:00 – Intro: JC Glancy’s founder success story begins
02:30 – Credit card debt & early startup struggles
06:15 – Building ZenBusiness into a unicorn startup
09:00 – Giving up the CEO title: The bold move
12:50 – How ZenBusiness outperformed LegalZoom
16:10 – Product market fit: Why the early products failed
19:45 – The SEO and affiliate marketing funnel that scaled
23:30 – Fundraising strategy: From angels to $200M Series C
28:20 – Building a powerful startup team without resources
32:10 – COVID pivot story: How ZenBusiness exploded in growth
37:00 – Recruiting top talent post-Series C
41:30 – Founder exit strategy: Why JC stepped back
45:00 – What JC is building next + advice for future unicorn founders
ABOUT JC GLANCY
JC Glancy is the co-founder of ZenBusiness, a unicorn startup that helps entrepreneurs launch and grow their businesses. From maxed-out credit cards to a $1B valuation, JC’s journey is a powerful founder success story. As head of product marketing, he built ZenBusiness’s marketing machine—driving explosive growth through SEO, affiliates, and data-driven customer insights. He gave up the CEO title, helped raise a $200M Series C, and led the company to outpace giants like LegalZoom.
Connect with JC:
LinkedIn:https://www.linkedin.com/in/jcglancy
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode79&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode79&utm_id=FundraisingDemystifiedPodcast
Here's what you're in for:
00:00 – Intro | How to attract influencers to your startup (Gil Eyal’s expert take)
02:15 – The truth about celebrity marketing (Why celebs care about startups)
05:30 – Biggest mistakes startups make with influencer marketing
09:45 – How to get access to celebrities & influencers (Stardust Ventures' insights)
13:20 – The power of storytelling in influencer marketing (Why authenticity wins)
17:05 – How to pitch your startup to influencers (Gil Eyal’s step-by-step strategy)
20:50 – Best platforms to connect with influencers (Where to find the right talent)
25:10 – How to structure influencer & celebrity deals (Equity vs. cash agreements)
29:40 – How celebrity partnerships impact startup valuations (Real success stories)
35:00 – The most effective marketing channels for startups (Gil Eyal’s top picks)
39:00 – B2B vs. B2C influencer marketing (How to make it work in different industries)
43:00 – Final advice from Gil Eyal on startup growth & fundraising
ABOUT GIL EYAL
Gil Eyal is a leading expert in celebrity endorsements and influencer marketing, known for revolutionizing how brands leverage data-driven influencer strategies. As the Founder and former President of HYPR, he built the market leader in influencer marketing automation, which won multiple industry awards before being acquired by Juliusworks in 2020.
A veteran of 200+ celebrity endorsement deals, Gil has worked with Leonardo DiCaprio, Serena Williams, Zendaya, Pitbull, and Stephen Curry, among others. Today, as the Founder of Stardust Ventures, Gil helps consumer startups scale through strategic celebrity partnerships.
You can reach out to Gil through:
Website Stardust Ventures: https://stardustventures.us/
LinkedIn: https://www.linkedin.com/in/gileyal/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with four multi-million exits and decades of experience in fundraising and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 to scale effectively. If you're a founder, investor, or entrepreneur, this is an episode you don’t want to miss!
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Raising capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode78&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode78&utm_id=FundraisingDemystifiedPodcast
Check out Chore: https://www.hirechore.com/partner/fundraising-demystified?utm_source=Podcast&utm_medium=Thunder_VC&utm_campaign=Fundraising+Demystified
What to expect from this episode:
00:00 – Why Founders Waste Time on the Wrong Things (and How to Fix It)
05:30 – The Brutal Truth About Startup Productivity Hacks
12:45 – How to Outsource Like a Pro and Scale Faster
18:20 – The Best Tools and Services to Automate Your Startup Ops
22:10 – The Harsh Reality of Starting a Business (What No One Tells You)
28:50 – The Biggest Mistakes That Lead to Founder Burnout and Failure
35:40 – The Ultimate Playbook for Making a Startup Successful
ABOUT ADAM SPECTOR
Adam Spector is a 4-time founder, startup advisor, and investor with experience in scaling companies and optimizing startup operations. As the CEO of Chore, he helps founders and teams focus on what matters by providing fractional chief-of-staff services to streamline back-office work. Adam has invested in over 200 startups, giving him unique insights into why startups fail and what it truly takes to succeed.
Chore Webiste: https://www.hirechore.com/
Adam Spector LinkedIn: https://www.linkedin.com/in/adamspector2/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 early-stage venture capital.
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Raising capital?
Get a list of vetted VCs for FREE here:
https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode77&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode77&utm_id=FundraisingDemystifiedPodcast
Here’s what you’ll find in this episode:
00:10 Avalanche Ventures Thesis
01:13 Identifying Market Trends
04:04 KatelynDonnelly's Background
06:28 Avalanche Ventures Investment Focus
07:28 Examples of Avalanche Investments
11:15 Solo GP Experience
13:03 Evaluating Investment Opportunities
14:41 Cold Emailing Advice for Founders
19:29 Austin's Startup Ecosystem
20:49 Venture Capital Insights
28:17 Future Market Trends
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ABOUT KATELYN DONNELLY
Katelyn Donnelly is the Managing Partner of Avalanche VC, an early-stage venture firm that invests in technology companies transforming how people learn, earn, and own. Her extensive background includes co-founding Delivery Associates, a leading public sector advisory firm, and serving as Managing Director of Pearson Ventures, a global EdTech venture fund. Donnelly's career also features time at McKinsey & Company, and she has been recognized for her achievements, including being named to Forbes 30 Under 30. She is actively involved in shaping the future of education and technology, and is a member of Duke University's Learning Innovation Advisory Council.
Connect with Katelyn:
Katelyn's Website: https://katelyndonnelly.com/
Avalanche VC Website: https://www.avalanche.vc/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: Jason Kirby
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 why capital efficiency matters more than high valuations.
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Raising capital?
Get a list of vetted VCs for FREE here:
https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode76&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode76&utm_id=FundraisingDemystifiedPodcast
IN THIS EPISODE
[00:00] Dave Lambert from Right Side Capital Management and Early-Stage Startup Investing
[02:15] What VCs Look for in Early-Stage Startups
[07:34] Fund Size and Unique Approach
[15:40] Valuation Trends and Market Dynamics
[07:34] RightSide Capital’s Unique Investment Strategy & Fund Size
[15:40] Startup Valuation Trends & Market Changes|
[17:29] AI’s Impact on Early-Stage Startup Investments
[20:42] Fundraising Challenges & How Founders Can Overcome Them
[27:36] Venture Capital vs. Bootstrapping: Choosing the Right Path
[29:04] The Role of Transparent Communication in Startup Fundraising
[31:18] How CEOs Should Manage Investor & Board Relations
[36:13] How to Provide Investor Updates That Build Trust
[43:36] Why Low Cash Burn is Critical for Early-Stage Startups
[45:33] The Future of Early-Stage Venture Capital & Startup Funding
[49:42] How to Connect with Dave Lambert
ABOUT DAVE LAMBERT
Dave Lambert is the Founder and Managing Partner of Right Side Capital Management (RSCM), a venture firm specializing in early-stage startup investing. With over 2,000 investments, RSCM focuses on capital-efficient tech startups, making fast investment decisions at valuations under $4M.
A former exited founder, Dave brings decades of experience in startup growth, fundraising strategies, and pre-seed investing.
Connect with Dave:
Right Side Capital Management Website: https://www.rightsidecapital.com/
Dave Lambert LinkedIn: https://www.linkedin.com/in/davidlambert55/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: jasonrkirby
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode75&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode75&utm_id=FundraisingDemystifiedPodcast
Here’s what you’ll find in this episode:
00:19 How Swag.com got to $40 Million in Sales
05:41 Wildest orders taken by Swag.com
06:47 How Swag.com started
15:35 Raising $3 Million in Venture Capital for Swag.com
21:38 Getting Acquired by Custom Ink
34:39 Advice for Founders
36:55 Connect with Jeremy Parker
ABOUT JEREMY PARKER
Jeremy Parker is the co-founder of Swag.com, a prominent e-commerce platform specializing in high-quality promotional products for businesses. His entrepreneurial journey began after graduating from Boston University, where he initially pursued film production. Parker's business background includes establishing a creative promotional product division and co-founding an e-commerce platform focused on social media influencer marketing, which was later acquired.
He then focused his efforts on Swag.com, which has seen rapid growth and attracted major clients like Facebook, Google, and Amazon. Notably, Swag.com was acquired by Custom Ink in 2021. Parker has also been recognized for his achievements, including being named to Crain's NY 40 under 40, and Swag.com has appeared on the Inc. 500 list of fastest-growing private companies.
Connect with Jeremy:
Email: [email protected]
LinkedIn: Jeremy Parker
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 capital and startup growth. We also explore Boardy AI, AI-assisted coding, and the rise of Chief AI Officers.
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Raising capital?
Get a list of vetted VCs for FREE here:
https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode74&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode74&utm_id=FundraisingDemystifiedPodcast
If you’re looking to maximize AI output and boost efficiency, this episode is packed with insights. Don’t forget to like, subscribe, and stay tuned for more!
Here’s what you’ll find in this episode:
00:00 - Introduction to Jon Tucker & HelpFlow
01:30 - AI’s impact on customer service & workforce
reduction
04:00 - The importance of Evaluating AI Performance
07:15 - How AI enables business efficiency and scalability
12:45 - AI’s role in startup growth and venture capital trends
18:30 - AI workflow automation & AI-assisted coding
24:00 - Future of AI: Chief AI Officers, automation, and
scaling
28:30 - Boardy AI and next-gen AI-powered networking
ABOUT JON TUCKER
Jon Tucker is the CEO atHelpFlow.com. Over the past decade, he’s managed remote teams and faced the frustrations of micromanaging every detail—an experience that drove him to embrace AI for smarter delegation.
Through HelpFlow’s “smart staff” model and their proprietary GuideLayer AI, Jon transforms traditional virtual assistants into high-value, autonomous team members. His goal? Free founders from busywork so they can scale faster and focus on what truly matters. Ready to see how AI can change the way you work? Try the AI at HelpFlow.com/demo-ai-video
Connect with Jon Tucker:
Website:HelpFlow.com
LinkedIn: https://www.linkedin.com/in/jontuckerusa/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn:https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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 company, or a growing e-commerce brand, this episode will help you avoid common fundraising mistakes and focus on strategies that align with your vision.------------------------------------------
Raising capital?
Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode73&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode73&utm_id=FundraisingDemystifiedPodcastHere’s what you’ll find in this episode:
00:00 Introduction to Fundraising Quadrants
00:32 Speaker's Background and Expertise
01:15 TheNorth Star framework: What do you really want to achieve?
03:42 What are the Fundraising Quadrants? Find out where you stand
05:29 Breaking down the quadrants: Early Growth, Established Growth, Strong but Slow,
Struggling
06:47 Venture Capital: When and how to attract investors (and when to avoid them!)
09:09 Debt Financing: Leveraging assets, revenue, and strategic borrowing
12:20 Private Equity: What PE firms look for & how to position your startup
15:16 Planning Your Exit: M&A, acquisitions, and strategic partnerships
18:24 The Big Question:Should you use investor money or bootstrap?
18:44 HowThunder VC helps founders navigate fundraising
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ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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, the challenge of getting a two-sided marketplace off the ground, and the inside story of negotiating his sale to Flippa.
Now leading Flippa Invest, Laurits is on a mission to help founders secure funding—without the pressure of chasing unicorn status. If you’re a founder weighing your options, this episode will open your eyes to paths beyond traditional VC.
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Raising capital?
Get a list of vetted VCs for FREE here:
https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode72&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode72&utm_id=FundraisingDemystifiedPodcastHere’s what you’ll find in this episode:
00:00: Introduction
01:40: The story behind the startup and bootstrapping
02:49: Overcoming the challenges of a two-sided marketplace
05:44: Growing profitably and attracting acquisition offers
06:03: Why Laurits and his co-founder decided to sell to Flippa
09:53: Bootstrapping vs. raising capital: The three-door dilemma
12:34: Running a competitive sale process for maximum exit value
18:10: Life after the acquisition: Transitioning to Flippa Invest
21:04: How Flippa Invest offers an alternative to VC funding
24:19: The types of businesses that fit the Flippa Invest model
28:12: Understanding valuation and fundraising expectations
36:45: How founders can explore funding through Flippa Invest
ABOUT LAURITS JUST
Laurits Just is the co-founder and co-CEO of BitsForDigits, a marketplace for partial and full business acquisitions. With a background in finance, he worked at BlackRock and Rocket Internet in London before launching his startup. Holding three degrees—including a Master of Science from the London School of Economics—Laurits specialized in digital innovation, AI applications, and distributed ledger platforms.
After leaving BlackRock, he co-founded BitsForDigits with a mission to provide liquidity solutions for self-funded business owners. Inspired by a blog post on Jeff Bezos' investment in Basecamp, he and his co-founder built a platform that made secondary transactions more accessible. After scaling the business to profitability, they ultimately exited to Flippa, where Laurits now leads Flippa Invest, helping founders secure funding beyond traditional VC.
Connect with Laurits:
Website: Flippa Invest
LinkedIn: Laurits Just
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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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.
In this episode, Penelope details her early challenges, fundraising strategies, and insights into scaling a utilities business sustainably and profitably. She also discusses her decision to step back from Rebel Energy and her vision for entrepreneurship in the UK.
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode71&utm_id=FundraisingDemystifiedPodcast
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode71&utm_id=FundraisingDemystifiedPodcast
Here’s what you’ll find in this episode:00:00 Introduction and Guest Welcome
00:25 Early Days and Initial Fundraising
01:39 Fundraising Strategies and Challenges
05:57 Crowdfunding Success and Market Entry
09:27 Growth Strategy and Operational Efficiency
14:06 Profitability and Future Plans
15:49 Stepping Down and Reflecting on the Journey
19:09 Advice for Founders and Fundraising Tips
22:06 UK Startup Ecosystem and Opportunities
32:55 Networking and Access to Investors
34:49 Conclusion and Final Thoughts
ABOUT PENELOPE HOPEPenelope Hope co-founded Rebel Energy, a UK-based renewable energy supplier with a mission to alleviate fuel poverty. Under her leadership, the company grew from its initial $1.5 million raise to achieving over $100 million in revenue while maintaining profitability from day one. A strong advocate of operational efficiency, Penelope leveraged automation to stay competitive in the fragmented UK energy market.
Penelope has a background as an equity analyst and a deep commitment to social and environmental missions. After stepping back from Rebel Energy, she continues to inspire founders by sharing her experiences and advocating for founder-led innovation.
Connect with PENELOPE:
LinkedIn: https://www.linkedin.com/in/penelope-hope/
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
-
After achieving financial success as a founder, David Goldberg shifted his focus to making a global impact. As the founder of Founders Pledge, David has pioneered a transformative approach to philanthropy, enabling entrepreneurs to commit a portion of their exit proceeds to charity. Over the past 10 years, Founders Pledge has deployed $1.3 billion toward impactful causes, making it one of the most innovative nonprofit organizations for founders.
David discusses the philosophy behind Founders Pledge, the challenges of creating a global philanthropic network, and the strategies for ensuring every dollar donated achieves measurable results.
Raising capital?
Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101
Here’s what you’ll find in this episode:
00:02 Introduction
00:16 David Goldberg’s journey from founder to philanthropist
03:50 The origins of Founders Pledge and its mission
08:00 How pledging future earnings fosters impact-driven giving
12:15 Deploying $1.3B: How Founders Pledge maximizes impact
20:30 The importance of trust and transparency in philanthropy
33:08 Scaling Founders Pledge: Challenges and aspirations
ABOUT DAVID GOLDBERGDavid Goldberg is the co-founder and CEO of Founders Pledge, a global nonprofit that empowers entrepreneurs to commit a portion of their exits to high-impact philanthropy. Under his leadership, the organization has grown to over 2,000 members across 40 countries, with nearly $11 billion pledged and $1.3 billion deployed to transformative causes. Driven by a mission to simplify and amplify meaningful change, David transitioned from a diverse commercial background to the nonprofit sector, blending his expertise in finance, startups, and academia.
Before Founders Pledge, David gained experience as a mortgage and investment banker and launched the secondary marketing department at Mortgage Capital Associates. A serial entrepreneur, he founded a boutique real estate firm in Germany and managed Urban Motion. He is a graduate of UCLA and the University of Cambridge, where he deepened his understanding of systems driving impactful change. Inspired by the desire to make philanthropy accessible, David has built a community where founders can harness their success to improve the world.
Connect with DAVID:
Website: www.founderspledge.com
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
-
From founding one of the earliest social media agencies to crafting an intentional path to a major eight-figure exit, Carrie Kerpen has redefined what it means to be a female entrepreneur in the digital age. In this episode, Carrie shares the transformative strategies she used to scale Likeable Media into a profitable and sellable business.
Carrie reveals her RED (Recurring, Expected, Diversified) revenue framework, discusses the importance of building businesses beyond the founder and provides insights into the challenges women founders face during the acquisition process.
_________________________
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101Here’s what you’ll find in this episode:
00:00 Introduction
00:15 Building Likeable Media and scaling one of the first social media agencies
04:15 The RED framework for making a business a sellable asset
10:10 The exit gap and its impact on women entrepreneurs
15:59 Why recurring revenue is key to a strong exit
22:05 Trends in M&A and the importance of AI in future acquisitions
33:20 Insights into The Whisper Way, Carrie's upcoming book
ABOUT CARRIE KERPEN
Carrie Kerpen is a trailblazing entrepreneur, author, and advocate for female founders. She built Likeable Media, a pioneer in the social media agency space, which scaled rapidly and achieved a major exit in 2021. Carrie now leads The Whisper Group, focusing on exit readiness for women-owned businesses, and is set to release her book The Whisper Way in May 2025.
Through her work, Carrie has empowered countless founders to dream big, execute strategic plans, and confidently navigate the exit process.
Connect with Carrie:
Website: CarrieKerpen.com
The Whisper Group: WeAreTheWhisperGroup.com
LinkedIn: Carrie Kerpen
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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From dog genetics to bootstrapping to an eight-figure exit , Conor Tomkies has done it all. As the founder of Support Ninja, Conor scaled a bootstrapped business into a middle eight-figure success story, managing thousands of employees worldwide. After selling to private equity, Conor is now building Operator Equity and Entrepreneur Cooperative, empowering founders to scale and exit with purpose.
Conor Tomkies shares how he leveraged strategic legal and operational efficiencies to save millions during acquisitions. He highlights his founder-first approach with Operator Equity, focused on scaling SaaS businesses using EOS, and discusses the startup shift from venture-backed moonshots to sustainable, profitable growth.
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Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101
Here's what you'll find in this episode:
00:00 Introduction
00:37 Dog genetics and the birth of Support Ninja
02:54 Bootstrapping vs. raising venture capital
05:30 Lessons from selling to private equity
10:14 Why EOS is a game-changer for scaling companies
18:34 Operator Equity’s focus on SaaS and ecosystem synergy
27:00 Common founder mistakes and the value of recurring revenue
30:45 The rise of moonshots and the future of venture capital
ABOUT CONOR TOMKIES
Conor Tomkies is a serial entrepreneur, investor, and post-exit founder with a passion for creating scalable businesses and empowering other entrepreneurs. He founded Support Ninja, a bootstrapped outsourcing company that scaled into a middle eight-figure success story and sold it to private equity. Now leading Operator Equity, Conor focuses on acquiring and scaling SaaS businesses using the Entrepreneurial Operating System (EOS), helping founders navigate successful exits with a streamlined 45-day process that prioritizes simplicity and a human touch.
Conor is also the co-founder of Entrepreneur Cooperative (ECo) and host of the Made It Podcast. Through ECo, he has built a community where seasoned founders share experiences, collaborate, and gain insider strategies for navigating business sales and life beyond the exit. It’s the network every entrepreneur wishes they had when starting out, focused on meaningful growth, impactful exits, and supporting the next generation of founders.
Connect with Conor:
Website: operatorequity.com
Entrepreneur Cooperative: entrepreneurcooperative.com
X (formerly Twitter): @conortomkies_
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
-
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101
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What does it take to build, scale, and sell a business—and then do it all over again? David Hauser, the mastermind behind Grasshopper and Vanilla, has done just that. Starting with his very first pitch to his father for a Dell computer, David went on to raise nine figures for Return Path, bootstrap Grasshopper into a $175M success, and disrupt estate planning with Vanilla.
But it hasn’t been all smooth sailing. In this episode, David opens up about the emotional aftermath of exiting a company, the identity struggles that follow, and how he found purpose by taking the leap into a new chapter. Now leading Durable Capital, David is focused on acquiring and scaling profitable companies while mentoring the next generation of founders.
Here's what you'll find in this episode:
00:00Trailer/ Introduction
01:23 Early days: From a Dell computer to Return Path
06:02 Bootstrapping Grasshopper to a $175M exit
18:26 Vanilla and the decision to raise $42M in venture capital
25:34 Navigating post-exit identity shifts and finding fulfillment
39:00 Durable Capital: Buying and scaling profitable businesses
41:28 Mentoring the next generation of founders
ABOUT DAVID HAUSER
David Hauser is a serial entrepreneur, investor, and speaker known for founding and scaling successful companies like Grasshopper (bootstrapped to $30M+ ARR, acquired by Citrix), Chargify (profitable, Mark Cuban-backed, acquired by Battery Ventures), and Vanilla (raised $42M from Venrock and Insight Partners). A founding member of National Entrepreneurs’ Day, he has also invested in over 50 startups, including Intercom and Unbounce. David’s insights have been featured in major outlets like CNN, Fox, and The Wall Street Journal, and he has spoken at renowned events such as SaaSFest and Big Omaha. Now leading Durable Capital from Las Vegas, he focuses on acquiring profitable businesses and mentoring the next generation of founders.
Connect with David on:
Website: www.davidhauser.com
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
-
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101
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What do a career coaching platform, a French-American football team, and a fraud prevention startup have in common? Meet Patrick Butler, the mind behind all three. Talk about a guy who doesn't do boring. One minute he's running a career coaching platform, the next he's starting a football team in Paris, and now he's crushing it with a fraud prevention startup called BizDefender.
In this episode, Patrick shares the details of how he's jumped between totally different worlds. We're talking crazy fundraising tricks, buying up companies most people would run from, and basically rewriting the rulebook on how startups actually work.
Seriously, who starts a pro football team as a side hustle? This guy. And he makes it sound like it's no big deal. It's the kind of story that makes you wonder: Are some people just wired differently? Patrick seems to turn wild ideas into businesses while most of us are still planning our next move.
Want to hear about breaking every conventional rule in entrepreneurship? This is your episode.
Here's what you'll find in this episode:
00:00 The Unlikely Pitch: Starting an American Football Team in France
00:48 Meet Patrick Butler: From Startup Success to Private Equity Exit
01:24 The Journey of Talent Inc.: From Struggles to Success
02:11 The Power of a Great Co-Founder: Meeting Jeff
03:29 Building Talent Inc.: The Resume Revolution
05:51 Scaling Up: Acquisitions and Growth Strategies
09:46 Navigating Fundraising: Debt, Equity, and Private Investors
19:59 Post-Exit Reflections: Life After Talent Inc.
21:30 A New Venture: Launching an American Football Team in Paris
25:51 Meeting a Nike Executive and Defining Our Vision
26:40 The Importance of a Brand Book
28:09 Convincing the French with American Football Culture
30:30 Economics of Starting a Football Team in France
31:51 Revenue Drivers and Merchandise
36:07 Launching BizDefender: A New Venture
41:13 Preventing Small Business Fraud with BizDefender
43:40 The Journey and Future of BizDefender
47:59 Final Thoughts and Contact Information
ABOUT PATRICK BUTLER
Patrick Butler is a serial entrepreneur, co-founder, and CEO of BizDefender, a first-of-its-kind fraud prevention tool for SMBs. His entrepreneurial achievements include leading Talent Inc. to a successful exit and co-founding a professional American football team in France. Patrick is passionate about creating impactful businesses while fostering innovation across industries.
Connect with Patrick on:
Website: www.pbutler.com
Biz Defender: www.bizdefender.com
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
-
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders
Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101
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Think debt is a trap? Think again. Learn how the right kind of debt can fuel your growth without sacrificing control of your startup. In this insightful episode, Jason Kirby welcomes Kyle Rector, co-founder and president of Boundless, to shed light on an often-overlooked aspect of startup funding: debt financing. If equity raises are the headlines, debt is the subplot that drives growth for countless businesses—but only if founders understand how to wield it wisely.
Kyle shares hard-earned wisdom from a decade of navigating the debt financing space, offering practical advice for founders at all stages. Kyle walks us through the spectrum of non-dilutive funding options, from the basics of debt vs. equity to the complexities of venture debt, revenue-based financing, and more. Whether you’re looking to extend runway, fuel expansion, or build sustainable operations, this episode equips you with the knowledge to make informed capital decisions.
Here's what you'll find in this episode:
00:00 Introduction to Debt Financing
00:08 Meet Kyle Rector: Debt Financing Expert
00:55 Understanding Debt vs Equity
03:41 Types of Debt for Businesses
08:27 Term Loans Explained
09:59 Lines of Credit: Flexible Financing
11:42 Secured vs Unsecured Financing
16:48 Venture Debt: A Strategic Option
22:23 Revenue-Based Financing: Pros and Cons
29:49 Exploring Different Types of Debt Financing
30:07 Valuing Contracts and Lines of Credit
32:56 Preparing to Secure Debt: Key Considerations
37:14 Understanding Debt Service Coverage Ratio (DSCR)
40:35 Benchmarking Debt Options for Different Business Profiles
51:47 Building Relationships and Trust with Lenders
54:05 Conclusion and Final Thoughts
ABOUT KYLE RECTOR
Kyle Rector is the co-founder and president of Boundless, a capital marketplace connecting businesses with lenders through tailored solutions. With over 10 years of experience in debt financing, Kyle has facilitated billions in capital requests, spanning industries and geographies. His mission with Boundless is to simplify the capital application process, enabling founders to focus on scaling their businesses.
Connect with Kyle on:
Webiste: www.getboundless.ai
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.
Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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