$100M Exits with Jason Kirby

In this episode of $100M Exits, Jason sits down with Dan Nguyen-Huu, Partner at Decibel Ventures, to unpack what early-stage specialist investing really looks like, from getting into Databricks at a $950M valuation to seeding Sublime Security before it raised a $150M Series C.

Dan breaks down how Decibel backs technical founders in cybersecurity, AI engineering, and developer tools, why contrarian bets only work if you deeply understand the domain, and what founders get catastrophically wrong about M&A, including why the one executive betting their career on you matters more than anything else in a deal.

He also shares the honest truth about failed bets, what to ask a VC before you take their money, and where the puck is heading in autonomous defense and the post-Mythos security landscape.

What You'll Learn:

• How Decibel got into Databricks and what made them pull the trigger on a competitive round

• Why being contrarian only works when you've done the domain homework

• The M&A truth founders miss: one executive is betting their career on you

• What separates "have" founders from "have-not" founders when bets go sideways

• Where Decibel is placing chips next — autonomous defense, agentic security, and the future of software vendors

  
  

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ABOUT DAN NGUYEN-HUUDan Nguyen-Huu is a Partner at Decibel VC, where he helps founders build next-generation cloud infrastructure, security, and AI companies from the earliest stage. With over a decade of investing experience, he has backed companies including Databricks, Sumo Logic, Matillion, Expel, and Contrast Security.

You can reach out to Dan through:

LinkedIn: https://www.linkedin.com/in/dan-nguyen-huu-11502719/?isSelfProfile=false

Website: https://www.decibel.vc/ - Company               https://dannguyenhuu.substack.com/ - Personal

X (twitter): https://x.com/dannguyenhuu

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ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+.

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

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ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

─────────────────────────────

The question you can't ask your board — you can ask https://exitboard.ai.

Should I take the LOI? Is this term sheet a trap? Am I underpricing the round?

ExitBoard gives you 100+ founders behind $10B in exits, on call, before you walk it into the boardroom.

Free. No sign-up. Ask anything → https://exitboard.ai

─────────────────────────────

Most bankers have never built a company. We have been in your shoes and exited.

Thunder was built by exited founders. 6,000+ post-exit founders in our network. $1B+ transacted. We work with VC-backed founders on debt, equity, recaps, and exits.

If you're exploring a transaction in 6-24 months, start a conversation with us → https://thunder.vc

In this episode of $100M Exits, Jason sits down with Itamar Novick, Founder and General Partner of Recursive Ventures, to unpack where the real value in AI will be created, why today’s AI infrastructure market looks increasingly like a bubble, and what founders need to build companies that can actually defend their position. Itamar has built and taken Life360 public twice and now backs early-stage AI companies at the application layer.

From AI infrastructure and application-layer valuations, to proprietary data, recursive learning loops, and the growing importance of domain expertise, Itamar shares how he thinks about AI moats, venture-scale businesses, and where founders should be careful about taking too much capital too early.

What You'll Learn:

• Why Itamar believes we're in an AI infrastructure bubble — and where he sees the real opportunity

• What makes an AI company defensible when building software is easier than ever

• Why founders should question whether their business is actually venture scale before taking VC money

• How "seed strapping" can help founders build toward cash flow positive growth

• Why AI founders need a Plan B for unit economics as today's token costs are heavily subsidized

ABOUT ITAMAR NOVICK

Itamar Novick is the Founder of Recursive Ventures, a pre-seed fund backing AI startups from day one. He has backed 100+ startups, including Deel, HoneyBook, Life360, and Tile, and was part of the early teams at Life360, which scaled from seed to IPO, and Gigya, which was acquired by SAP for $350M. Business Insider has named him a Top 100 global seed investor every year since 2022. 

You can reach out to Itamar through:

LinkedIn: https://www.linkedin.com/in/itamarnovick/overlay/contact-info/

Website: https://www.recursiveventures.com/ - Company               

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

─────────────────────────────

The question you can't ask your board — you can ask https://exitboard.ai.

Should I take the LOI? Is this term sheet a trap? Am I underpricing the round?

ExitBoard gives you 100+ founders behind $10B in exits, on call, before you walk it into the boardroom.

Free. No sign-up. Ask anything → https://exitboard.ai

─────────────────────────────

Most bankers have never built a company. We have been in your shoes and exited.

Thunder was built by exited founders. 6,000+ post-exit founders in our network. $1B+ transacted. We work with VC-backed founders on debt, equity, recaps, and exits.

If you're exploring a transaction in 6-24 months, start a conversation with us → https://thunder.vc 

In this episode of $100M Exits, Jason sits down with Erik Huberman, Founder and CEO of Hawke Media, to unpack what it really takes to run a programmatic M&A strategy, back early-stage founders, and scale a media agency to $750M in gross revenue, all at the same time. Erik has done 24 acquisitions, invested in 120+ companies, and has the battle scars to prove what works and what blows up.

From structuring 100% earn-out deals with no upfront cash, to betting on founders over ideas, Erik shares a no-filter look at how he thinks about buying companies, writing checks, and building infrastructure that lets others grow faster than they could alone.

What You'll Learn:

• Why Erik pays zero cash upfront on acquisitions — and why founders still prefer his deals

• What he looks for before writing a check (hint: it's not the idea)

• The biggest mistake founders make on the sell side: ego over realism

• Why early-stage software is now one of the riskiest bets in venture

• When a founder should actually consider inorganic growth — and when it's too soon

  
  

Here’s what you’re in for:

00:00 – Intro & Erik's Background

01:00 – Why Hawke Media Buys Companies

05:00 – What Makes an Agency Worth Acquiring

07:00 – How Deals Are Valued & Structured

11:00 – The 100% Earn-Out Model Explained

13:00 – Sell-Side Mistakes Founders Make

20:00 – When Deals Fall Apart Post-Close

22:00 – From Angel Investing to Running a Fund

26:00 – Best Investments: Postscript, Klaviyo & Telly

31:00 – What Erik Looks for in Early-Stage Founders

40:00 – Advice for Founders at $5M–$50M

44:00 – Markets Erik Is Avoiding Right Now

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=EP+120&utm_campaign=%24100M+Exits  

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+120&utm_campaign=%24100M+Exits  

ABOUT ERIK HUBERMAN

Erik Huberman is the Founder and CEO of Hawke Media, a marketing consultancy built on the idea that every business deserves access to CMO-level expertise without the overhead of a traditional agency. After founding and selling two e-commerce companies before age 26, he bootstrapped Hawke Media into a nationally recognized firm that has helped more than 5,000 brands scale.

Beyond Hawke Media, Erik leads Hawke Ventures and Hawke.AI, investing in startups and building data-driven tools that help businesses make smarter marketing decisions.

You can reach out to Erik through:

LinkedIn: https://www.linkedin.com/in/erikhuberman/

Website: https://www.hawkemedia.com - Company               https://www.erikhuberman.com - Personal

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

In this episode of $100M Exits, Jason sits down with Brian Rosen of InvestBev Capital to unpack what it really takes to sell a family business, build from scratch, and then deploy $300M backing the founders most investors overlook. Brian has lived every side of the deal table — operator, seller, and now investor — and he's not holding back on what he got wrong the first time.

Brian scaled his family's liquor business from $30M to $100M in revenue, sold to PE, then built and sold BevStrat for $20M+ in just four years. Today he manages over $300M in AUM through InvestBev, one of the few firms exclusively focused on the alcohol beverage category — including a unique bet on bourbon barrel inventory that now holds roughly 10% of the country's supply.

What You'll Learn:

• Why selling too much equity early cost Brian ~$10M and what to do differently

• How a strategic buyer will always outpay a financial buyer

• Why celebrity brand deals are a trap and what actually drives brand success

• The real reason 95% of beverage brands fail — and how to be in the 5%

• Why alcohol is one of the most non-correlated asset classes available to investors

  
  

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=EP+119&utm_campaign=%24100M+Exits  

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+119&utm_campaign=%24100M+Exits  

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ABOUT BRIAN ROSEN

Brian Rosen is the CEO and General Partner of InvestBev Capital, the largest private equity platform in the U.S. dedicated to the spirits, wine, and beverage CPG sectors. He has scaled the firm to $350M AUM and $100M in private credit, supporting brands across all stages of growth while delivering first-quartile returns.

With deep roots in the beverage industry across three generations, Brian has led M&A transactions, structured innovative financing solutions, and partnered with global leaders like Beam Suntory and BlackRock. He is recognized as a leading voice in alcohol beverage investing and a key builder of the modern global spirits investment ecosystem.

You can reach out to Brian through:

LinkedIn: https://www.linkedin.com/in/briandavidrosen  

Website: https://www.investbev.com - Company

Email: [email protected] 

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+.

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

In this episode of $100M Exits, Jason sits down with Jim Ferry of Volition Capital to unpack what’s really happening inside growth equity, AI-driven dealmaking, and today’s frozen liquidity market.

Managing over $1.8B in growth equity, Jim explains how the market has shifted from easy capital and inflated SaaS multiples to a brutal divide between the “haves and have-nots.” He breaks down why investment committees are stalling deals, why founders are being forced to rethink exits, and how AI is rapidly becoming the deciding factor between survival and irrelevance.

The conversation dives deep into what growth equity firms actually look for, how deal structures work behind the scenes, and why many founders misunderstand the moment they’re truly ready to scale. Jim also shares lessons from contrarian bets in ad tech, failed hyper-local rollouts, and the hidden dynamics that kill M&A deals in the final hour.

They also explore:

• Why every company now needs to become AI-native

• The dangerous gap between public and private market valuations

• How PE firms think during market corrections

• What causes acquisition deals to collapse mid-process

• Why missing projections is a “death sentence” in M&A

• The new reality of SaaS valuations and AI premiums

• How great founders pivot before disruption kills the business

This is a candid look inside the boardroom conversations shaping the next generation of exits, acquisitions, and AI-native companies.

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=EP+118&utm_campaign=%24100M+Exits  

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+118&utm_campaign=%24100M+Exits  

ABOUT JIM FERRY

Jim Ferry joined Volition Capital in 2014 and focuses on evaluating and supporting investment opportunities across internet and consumer businesses, including marketplaces, ad tech, consolidation platforms, and transactional companies. He works closely with founders and portfolio companies, serving on the boards of several high-growth businesses, including Aditude, Doing Things, Keynes, Linkby, Revi, and Rounds.

Jim is known for his partnership-driven approach to investing, spending much of his time working directly with entrepreneurs to help them navigate growth and scale their businesses.

You can reach out to Jim through:

LinkedIn: https://www.linkedin.com/in/jim-ferry-91b33375 

Twitter: https://www.jimferryvc

Website: https://www.volitioncapital.com/

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

In this episode of $100M Exits, Jeff Stewart breaks down why the venture capital and IPO system has fundamentally shifted—and what founders are getting wrong about scale, liquidity, and global capital markets.

Jeff shares his experience raising and transacting over $100M across his own companies, investing over $100M through his fund, and leading more than $500M in total deal flow. The conversation dives deep into why the U.S. public markets have evolved into a “mega-cap only” game, why secondary markets create hidden risks, and why global listings are becoming a strategic advantage—not an alternative.

The discussion also unpacks how founders should think about IPOs not as exits, but as long-term capital infrastructure. Jeff explains how public markets unlock talent, revenue, acquisition flexibility, and investor access in ways private markets increasingly cannot match.

Key insights include:

• Why the VC model incentivizes longer private cycles—but not always founder outcomes

• The rise (and risks) of secondary markets and SPV structures

• Why transparency and liquidity drive better capital allocation

• How global investors are reshaping IPO strategy

• Why “unit economics clarity” is the real IPO readiness test

• The difference between a “funding event” and a “capital system.”

This is a sharp, sometimes contrarian look at where capital markets are heading—and how founders can position themselves to win in a global IPO landscape.

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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=EP+117&utm_campaign=%24100M+Exits  

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+117&utm_campaign=%24100M+Exits  

ABOUT JEFFREY STEWART

Jeffrey Stewart is an inventor, entrepreneur, investor, and author focused on technology-enabled businesses and global capital markets. He is the author of Global IPO – The Great Rewiring of Capital Markets and works with GPO Fund, where he backs growth-stage tech founders building globally scalable companies.

Through the GPO Fund, Jeffrey invests in companies across emerging markets, B2B SaaS, clean-tech, education, blockchain, big data, and financial services, with a focus on improving how venture capital and global capital markets operate.

You can reach out to Jeff through:

LinkedIn:https://www.linkedin.com/in/stewartjeffrey 

Website: https://www.youtube.com 

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+.

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

Drew Allen didn’t start Grace Technologies — he inherited it.

But stepping into a family business isn’t just a continuation. It’s pressure: legacy, expectations, and the challenge of evolving something that already works without breaking it.

In this episode, Drew shares what it’s really like taking over as CEO of a family-founded industrial tech company, and the mindset shift required when preservation meets reinvention.

From international experience in Hong Kong to leading a U.S. Midwest manufacturing and safety tech business, he breaks down how Grace Technologies evolved from a traditional engineering firm into a full-stack industrial innovation platform.

At the core of it all is a bigger question: How do you make a “boring business” not boring, and why does that transformation matter more than it seems?

Why It Matters:

This isn’t just a family business story; it’s about turning inherited structure into a system that can innovate.

Drew shows that scale isn’t only driven by capital or speed, but by control of technology, clarity of vision, and building systems that evolve faster than the market.

In industrial sectors — safety, manufacturing, infrastructure — most people overlook that adaptability can be the difference between downtime and danger.

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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=EP+116&utm_campaign=%24100M+Exits  

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+116&utm_campaign=%24100M+Exits  

ABOUT DREW ALLEN 

Drew Allen is the CEO of Grace Technologies, where he leads the development and global distribution of innovative industrial technologies. A recipient of the National Association of Manufacturers’ 2020 Next-Generation Leadership Award, Drew has built his career around business development, international sales, product innovation, and family business leadership.

Beyond Grace Technologies, Drew also serves as CEO of Percev, LLC and sits on the advisory board of Atom Power, bringing a strong passion for technology, product design, and scaling impactful businesses worldwide.

You can reach out to Drew through:

LinkedIn: https://www.linkedin.com/in/allendrew 

Website: https://www.graceport.com 

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

From buying a messy manufacturing business with 26 plants to building a $100M EBITDA powerhouse, here's how it really happened.

For two decades, Eric Wiklendt has bought manufacturing businesses most PE firms avoid—and turned them into massively more valuable companies. Eric Wicklendt, Partner and Managing Director at Speyside Equity, has built a career around acquiring underloved, underperforming manufacturing businesses and transforming them into platforms worth exponentially more than what they paid.

In this episode, Eric breaks down the real story behind Speyside's origin, their signature "fix and build" strategy, and the Opta deal that became a masterclass in manufacturing transformation. He shares why most PE firms rely on hope as a strategy, how free cash flow tells the truth EBITDA can hide, and what it actually takes to turn around a business with 26 manufacturing plants in 18 months.

If you're a founder, operator, or investor in the manufacturing space, this episode is packed with hard-earned, battle-tested insight.

What you'll learn in this episode:

• How Speyside turned a $300K 401(k) bet into a manufacturing PE firm

• Why other PE firms avoided Opta—and why Speyside leaned in

• How operational improvements alone drove a 10X EBITDA increase

• Why free cash flow reveals what adjusted EBITDA hides

• What founders should know before choosing PE over a strategic buyer

  
  

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=EP+115&utm_campaign=%24100M+Exits 

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=EP+115&utm_campaign=%24100M+Exits 

ABOUT ERIC WIKLENDT 

Eric Wiklendt is a Managing Director and Partner at Speyside Equity, where he leads the sourcing, execution, management, and exit of investments while serving on the boards of several portfolio companies. Before joining Speyside, he held senior operational and leadership roles, including President & CEO of Kelix Heat Transfer Systems, as well as leadership positions at Eaton and Hilti Corporation, overseeing M&A, manufacturing, marketing, and industrial sales operations. 

You can reach out to Eric through:

LinkedIn:https://www.linkedin.com/in/ericwiklendt 

Website: https://speysideequity.com/ 

Email: [email protected] 

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

He built a company, sold it, and suddenly had millions in the bank. Here’s what no one tells you about what comes next. 

He bootstrapped a health tech SaaS company for 10 years and sold it to Agilent Technologies.

Sriram Gollapalli went from grinding as a founder to managing millions overnight—and realized that making money and managing money are two completely different games.

In this episode, he breaks down what founders don’t expect after an exit: the pressure of sudden wealth, the trap of overthinking investments, and why so many founders freeze when cash is just sitting in the bank. He shares how choosing the right buyer goes beyond valuation, why culture fit matters more than most realize, and the biggest mistakes he sees founders make when trying to invest in their exit.

If you’re a founder building toward an exit—or already have one—this is the side of the journey no one prepares you for.

What you’ll learn in this episode:

• How Sriram bootstrapped and exited his company after 10 years

• Why culture fit matters more than price in an acquisition

• The biggest mistake founders make when cash hits their bank account

• Why trying to time the market can cost you millions

• The difference between being a great founder and a great investor

• Why many founders hesitate to spend on themselves—even after a big exit

• How to think about diversification beyond just stocks

• What most founders get wrong about managing wealth after liquidity

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=EP+114&utm_campaign=%24100M+Exits 

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+114&utm_campaign=%24100M+Exits

Here's what you're in for:

00:00 Welcome and Guest Intro

00:40 Building iLab Bootstrapped

01:15 Running the Sale Process

02:12 Choosing Agilent and Deal Terms

04:24 Culture Fit and RSU Earnouts

08:03 Deal Lessons and Next Steps

10:22 Managing Money After Exit

13:29 Founder DIY vs Advisors

16:42 Biggest Post-Exit Mistakes

23:51 Why Long Angle Exists

27:10 Inside the Community Offerings

30:11 Diversification and Private Markets

39:33 Founder vs Employee Behaviors

43:45 Advice for Newly Liquid Founders

47:37 How to Join and Closing

ABOUT SRIRAM GOLLAPALLI  

Sriram Gollapalli is a former tech founder and investor. He co-founded iLab Solutions, a health tech SaaS company he bootstrapped for over a decade before selling to Agilent Technologies. After his exit, he shifted his focus to investing and is now the co-founder of Long Angle, a private community for high-net-worth individuals focused on wealth, investing, and life after liquidity. 

You can reach out to Sriram through:

LinkedIn: https://www.linkedin.com/in/sriramg/

Email:  [email protected]

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.

Most founders waste money right after raising it.

Dipak Patel breaks down one of the biggest mistakes founders make after raising capital—hiring too fast and burning cash. Instead, the focus should be on using that money wisely and creating real value.

His mindset is simple: treat every dollar like a loan. Even if it feels like free money, it comes with expectations. The best founders stay lean, hire carefully, and focus on efficiency before scaling.

Rather than rushing into expensive senior hires, Dipak shares why it’s better to bring in the right people, give them ownership, and let them help build smarter systems first.

If you’re raising money or planning to, this episode is a powerful reminder that discipline,not spending,is what drives long-term success.

What you’ll learn in this episode:

• Why most founders waste money after raising capital

• How to think about investor money the right way

• Why every dollar should be treated like a loan

• The importance of staying lean early on

• How to hire smart and build efficiently

• How to avoid burning cash too fast 

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=EP+113&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+113&utm_campaign=%24100M+Exits

Here's what you're in for:

00:00 Guest Welcome

01:17 Spending With Payback Mindset

01:32 Staying Lean and Hiring Lessons

01:40 Equity and Efficiency Goals

02:01 Stay Lean as a Founder

02:30 Why They Sold and Exit Mindset

03:02 What Gato Built in PropTech

03:49 Listening to CRE Pain Points

04:32 Dashboards Tickets and Waste Data

06:16 M&A Sale Mistakes and Advisors

10:35 Founder Takeaways on Cash and Raises

12:03 Life After Acquisition and Earnout Reality

15:40 Post Exit Reset and New Chapter

16:01 Learning Food Tech Sales at Fuda

18:25 COVID Pivot and CloudKitchens Consulting

19:46 Joining NAO and Choosing Equity

22:39 Scaling NAO Starts With CAC

23:14 Fixing Ad Spend Targeting

24:03 Referral Engine That Closes

25:44 Cookie Outreach Playbook

29:47 From Cookies to Healthcare Pivot

34:18 Where Health Tech Is Going

38:33 Winners Losers and AI Risk

42:31 Consolidation and Startup Survival

45:46 Closing

ABOUT DIPAK PATEL 

Dipak Patel is an LCRO and operator, and a SaaS revenue expert. He is a 2x exited founder and has helped drive over $232M+ in ARR across the companies he’s worked with.

He specializes in building go-to-market strategies for VC and private equity-backed companies, helping them grow efficiently and scale revenue. Dipak is also an advisor and investor, known for his focus on capital discipline and smart growth.

You can reach out to Dipak through:

LinkedIn: https://www.linkedin.com/in/dipakrpatel/

ABOUT JASON KIRBY

Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. 

He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+

You can reach out to Jason through:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/jasonrkirby/

ABOUT $100M EXITS

My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. 

For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. 

Be sure to subscribe and let me know who you want me to interview next.