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.

He built a $100M creator platform—and sold it twice. Here’s what actually happens after the deal closes.

Daniel Rosenberg, cofounder of Represent.com, shares how he helped creators and celebrities sell products without upfront cost using on-demand production. This removed the biggest barrier for creators: launching a business without upfront cost or inventory risk.

In this episode, he explains how Represent grew by working with top talent, why they focused on fewer, higher-value creators, and the risks that came with scaling fast. He also breaks down what really happens when you sell a company—from long deal processes to post-acquisition challenges.

Daniel also shares how the creator economy is changing. Today, creators don’t just want sponsorships—they want ownership and equity.

What you’ll learn in this episode:If you’re building a startup or thinking about exits, this episode gives you real, practical insights.

• How creators sell products without upfront cost

• Why choosing the right market matters

• The risks of scaling through big deals

• What actually happens during an acquisition

• Why many deals fall apart

• How the creator economy is shifting toward ownership

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+112&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+Exits

Here's what you're in for:

00:00 Meet Daniel Rosenberg 

00:49 Represent Origin Story

03:07 Landing Big Talent

05:26 Growth Engine Explained

07:49 Mayweather Cash Drop

10:06 Licensing With Major IP

11:01 Affiliate Versus Celebrity Focus

15:05 Custom Ink Acquisition

18:18 Deal Terms And Earnout

19:59 Diligence Distraction Lessons

21:40 Post Merger Integration

25:10 Selling To Cameo

29:37 Cameo Integration Reality Check

33:33 Why Dan Stepped Away

35:51 Ownership Shift In Creator Economy

38:20 Partnering With Creators

40:57 Risks And Who Should Worry

43:12 Resources And Closing

ABOUT DANIEL ROSENBERG 

Daniel “Dan” Rosenberg is a founder and entrepreneur best known for building Represent.com, a platform that helped creators and celebrities sell merchandise without upfront cost.

He scaled the company to a $100M+ exit, selling it to Custom Ink, and later helped lead another sale to Cameo.

Today, he focuses on the creator economy through Material Group, where he works with creators to build businesses where they have ownership—not just sponsorship deals.

You can reach out to Daniel through:

LinkedIn: https://www.linkedin.com/in/danielrosenberg1/ 

Website: https://www.materialgroup.co/ 

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 much 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 building startups to backing the future of warfare, this episode covers what founders need to know about capital, defense tech, and AI.

Brad Harrison, Founder and Managing Partner of Scout Ventures, shares how fast defense technology is evolving—and why selling into this space is harder than most expect.

He explains how AI, drones, and autonomous systems are reshaping warfare, and why success requires more than a strong product—founders need the right networks, industry insight, and an understanding of government buyers.

The conversation also covers how deals work in defense tech, what investors look for, and why choosing the right capital matters—especially when navigating government contracts.

If you’re a founder, investor, or operator in AI, defense, or emerging tech, this episode offers a clear view on how to build and fund in this space.

What you’ll learn:

• How operator experience shapes investment decisions
• Why defense tech innovation is accelerating
• How AI and autonomous systems are changing warfare
• Why startups struggle with defense procurement
• What gets funded in defense tech today
• How to align with real government demand
• Why networks and relationships matter
• What drives successful outcomes and exits
• Why understanding the end buyer is critical
• How capital strategy impacts growth

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+111&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+Exits

Here's what you're in for:

00:00 Entrepreneur Journey

01:55 Founder Support at Scout

03:46 Army Futures Command Shift

05:17 Ukraine Drone Autonomy Leap

08:12 Why US Procurement Lags

10:53 Key Defense Tech Domains

12:43 GPS Denied Navigation

15:17 Next Gen Wireless 6G

18:44 Founder Goals and Focus

20:43 Red Flags and Hard Calls

23:57 What Gets Funded Now

28:19 Vendor Lock Risks

29:11 AI Security Threats

30:31 Autonomy Changes Warfare

31:50 Selling to the Pentagon

32:27 RFPs, TRLs, and SBIRs

35:48 Lobbying and Budgets

38:28 Founder Insight Advantage

41:16 Tomahawk Robotics Exit

44:32 Defense Tech M&A Drivers

49:39 Scout Fund Strategy

51:53 Space Deterrence Vision

56:32 Founder Upside and Wrap

ABOUT BRAD HARRISON 

Brad Harrison is the Founder and Managing Partner of Scout Ventures, backing companies like ID.me, Voyager Space, and Tomahawk Robotics.

A former U.S. Army Airborne Ranger and West Point graduate, he later studied at MIT Sloan, focusing on building new ventures.

He has advised leaders at the White House and Pentagon on defense and innovation, and is now based in Austin, Texas.

You can reach out to Brad through:

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

Website: ⁠https://www.scout.vc/⁠ 

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 building and exiting companies to deploying capital at a $1.8B investment firm, George Alifragis has seen both sides—as an operator and now a private credit investor at Metropolitan.

In this episode, he breaks down the transition from operator to investor, lessons from scaling a global tech company, and how that shapes how he evaluates businesses today.

He shares what really drives EBITDA growth, what makes a company attractive to private equity, and why operators often misunderstand how investors think about risk, growth, and returns.

If you’re a founder thinking about exits or capital, this is a clear inside look.

What you’ll learn in this episode:

• What changes when you go from operator to investor

• How George scaled a global tech company and drove EBITDA growth

• What makes a business attractive to private equity buyers

• The key differences between big corporations and mid-sized companies

• Why growth operators thrive in different environments

• How investors actually evaluate risk and opportunity

• Lessons from exiting companies to TELUS and a PE-backed firm

• Why understanding the capital strategy is critical for a founder

  
  

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+110&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+Exits

Here's what you're in for:

00:00 Welcome and George Alifragis Intro

00:57 Operator Exits and Track Record

02:32 From Bell to Building Altima Telecom

07:24 Why He Left Corporate Life

10:43 Regulation That Forced an Exit

13:56 Moving to Miami and a New Chapter

15:17 Scaling to a Successful Exit

16:53 From Operator to Investor

21:43 Inside Metropolitan’s Investment Thesis

25:14 The Power of an Operator Network

27:01 The Operating Experts Model Explained

27:52 The Fishing Holes Investment Strategy

28:47 Building an Ecosystem Partner Network

30:12 Activating the Network at Scale

32:21 The Deal Flow Flywheel

34:30 How Deals Get Done at Metropolitan

37:45 Alternative Capital Explained

39:22 Structuring Bespoke Hybrid Deals

45:07 A Real Deal Structure Breakdown

50:25 Lessons on Cost of Capital

53:53 Final Thoughts and How to Connect

ABOUT GEORGE ALIFRAGIS 

George Alifragis is a multi-time operator turned investor, currently at Metropolitan, a $1.8B private credit firm, bringing experience from scaling companies, driving EBITDA growth, and evaluating businesses through an investor lens.
He previously served as CEO of a global tech company, leading growth and exiting to a private equity-backed firm, and was earlier part of a successful exit to TELUS, one of Canada’s largest telecom companies.

You can reach out to George through:

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

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.

Jess Mah has built, scaled, and backed companies across multiple waves of Silicon Valley—but what she’s seeing now is different.

In this episode of $100M Exits, she explains why even unicorn founders are under pressure in the AI era, where success is no longer about headcount, hype, or old playbooks. AI is compressing execution timelines, raising the bar for traction, and making many traditional founder skills feel outdated.

Jess breaks down why relevance, speed, and adaptability now matter more than funding or past wins—and why many experienced founders are struggling to adjust. She also shares how to build lean, AI-first companies, protect your edge, use relationships as market intelligence, and why micro-teams may outperform bloated organizations.

If you’re a founder navigating AI disruption, fundraising pressure, and shifting rules of company building, this conversation is a sharp reality check.

What you’ll learn in this episode:
• How AI is creating pressure even among unicorn founders
• Why relevance and speed now matter more than money or status
• What founders must unlearn to stay competitive
• Why lean teams and micro-teams can outperform larger organizations
• How to use side projects to rebuild your AI instincts and leadership edge
• Why protecting your information edge matters more than ever

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+109&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:
https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+109&utm_campaign=%24100M+Exits

Here's what you're in for:
00:00 Meet Jess Mah
01:21 Silicon Valley Stress
04:03 Money Versus Relevance
06:12 AI is changing the game
11:06 Founders React Poorly
14:17 Lean Teams And Traction
16:37 Funding Bar Keeps Rising
19:33 Differentiation And Wedges
22:15 Bias In Venture Funding
28:43 AI As Equalizer
31:30 Multi-Project Mindset
33:56 Building Quietly In Public
38:17 Networking As Market Radar
42:19 Protecting Your Information Edge
50:07 Side Hustles For Legacy Founders
56:40 Micro Teams And Reorg Reality
59:22 Leadership Reset And Farewell

ABOUT JESS MAH

Jessica Ma is a serial entrepreneur, investor, and venture builder known for launching and scaling multiple technology companies in Silicon Valley. She founded her first startup while still in college and scaled it to a nine-figure valuation after Y Combinator. Since then, she has founded and incubated more than 10 companies with combined valuations exceeding $1 billion. Today, she focuses on AI-driven ventures and shares insights on how AI is reshaping company building.

You can reach out to Jess through:
LinkedIn: https://www.linkedin.com/in/jessicamah/
Website: https://www.mahway.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.

Chris Wichert raised roughly $20M to build a modern luxury sneaker brand, pitching Koio as the “Louis Vuitton for millennials.” After business school, he moved to New York and secured investors, including the Winklevoss twins, Founders Fund, and the founder of Aldo, scaling through press, retail experiments, and premium positioning.

Then COVID hit. Retail revenue disappeared. Demand for dress sneakers collapsed. By early 2023, Koio faced roughly -$3M EBITDA in a market where DTC multiples had compressed and fundraising slowed dramatically.

In this episode, Chris shares how they reset the business: cutting 40% of SKUs, reducing headcount by 70%, going remote-first, closing most stores, and removing $3M in costs without sacrificing revenue, returning the company to profitability.

He also breaks down their exit process: running 200+ buyer conversations, navigating last-minute tariff-related deal risk, and ultimately selling to a Miami family office.

If you’re a founder navigating scale, crisis, or exit timing, this episode offers a candid look at capital strategy, cost discipline, and realistic decision-making.

What you’ll learn:

• Why early fundraising is about vision, not just numbers

• How retail experiments validated a luxury DTC brand

• What happens when DTC multiples collapse

• How to cut millions in costs without shrinking revenue

• Why founders delay tough restructuring decisions

• How to run a disciplined, proactive M&A process

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+108&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+108&utm_campaign=%24100M+Exits

Here's what you're in for:
00:00 Meet Koio Founder
00:59 Why Raise Early Capital
04:43 Retail Growth Playbook
08:55 COVID Shock and DTC Reset
15:51 Turnaround and Investor Realignment
29:19 Choosing a Full Sale
30:24 Building the Buyer Universe
33:26 Tariffs Shake the Deal
39:43 Founder Realism Shift
52:43 Capital Traps and Exit Advice

ABOUT CHRIS WICHERT

Chris Wichert is an entrepreneur and operator best known as the founder of Koio, a digitally native luxury sneaker brand built on craftsmanship and modern positioning. After raising ~$20M in venture capital, he scaled the business through retail expansion and premium brand building before navigating COVID and the broader DTC market collapse.

Facing compressed multiples and a shifting capital environment, Chris led a full operational reset — cutting costs, restructuring the team, and restoring profitability — before successfully exiting to a family office. He now speaks and advises on capital strategy, turnaround execution, and proactive exit planning.

You can reach out to Chris through:

LinkedIn: https://www.linkedin.com/in/chris-wichert1/
Website: https://ccatalyst.co/

ABOUT JASON KIRBY

Jason Kirby is co-founder of Thunder, a tech-enabled investment bank helping founders reach ideal 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, having coached hundreds of entrepreneurs and transacted over $135M personally; 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: equip founders with knowledge, inspiration, and guidance to navigate capital strategy by interviewing founders and investors who’ve done it. For most, a $100M+ exit is a dream; for others, cash flow or IPO matters. Founders doing over $5M in revenue benefit the most from this podcast.

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

From near bankruptcy… to a $700M strategic exit. Here’s how it actually happened.

Brian Ree built DailyLook into a premium AI-powered personal styling brand, nearly lost it in 2014, rebuilt it around ruthless unit economics and LTV, merged with Adore Me, and ultimately exited to Victoria’s Secret in a $700 million transaction.

In this episode, Brian breaks down the real story behind the pivot that almost killed the company, the $40 styling fee gamble that saved it, how focusing obsessively on lifetime value created a defensible moat, and why relationships drive major exits.

He also shares how DailyLook scaled from $30M to $140M post-acquisition, what it’s really like operating inside a public company, and why building a fashion brand is a decade-long grind, not a hype cycle.

If you’re building in DTC, fashion, subscription, or thinking about a strategic exit, this is a masterclass in resilience, economics, and timing.

What you’ll learn in this episode:

• How DailyLook built a premium styling subscription powered by AI + human stylists

• Why negative unit economics nearly killed the company in 2014

• The $40 pricing decision that turned the business around

• How obsessing over LTV created a long-term competitive moat

• Why most DTC brands fail to control CAC and retention

• How relationships led to the Adore Me merger and Victoria’s Secret acquisition

• What it’s like scaling from $50M to $140M inside a public company

• Why building a fashion brand is a 10+ year commitment
  

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+107&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+107&utm_campaign=%24100M+Exits

For full episode shownotes and resources, view them here.

From raising $100M from SoftBank to shifting from “growth at all costs” to building a durable business, Kris shares the real story behind scaling Sendoso to over $100M in revenue.

In this episode of $100M Exits, Kris walks through what it was actually like pitching Masayoshi Son over Zoom, deploying nine figures into aggressive hiring, then quickly pivoting when the zero-interest-rate era ended. He breaks down the hard decisions around efficiency, acquisitions, AI-driven sales automation, international expansion, and why building a 100-person advisory network became his secret weapon.

This isn’t just a fundraising story. It’s a lesson in adapting fast, evolving as a leader, and making bold moves when the market shifts.

If you're building toward nine figures in revenue — or trying to survive the jump from hypergrowth to operational discipline — this episode is packed with real-world insight.

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+106&utm_campaign=%24100M+Exits

Get the latest fundraising insights, news, and tips:

https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+106&utm_campaign=%24100M+Exits

Here's what you're in for:

00:00 Welcome and Kris from Sendoso

00:36 How SoftBank found Sendoso

02:07 The call with Masayoshi Son

04:46 What Kris did after the $100M landed

09:20 Using AI to scale sales without more headcount

12:11 Switching from hypergrowth to efficiency

16:32 Why Sendoso bought competitors

25:58 Making the merger work day one

27:18 The integration plan that kept it on track

28:03 Who they kept and who they didn’t

28:46 The tech migration and what took longer

29:47 M&A advice for founders

31:00 Talking to competitors before you need to

33:15 Why Kris chose a co-CEO setup

38:49 How Sendoso expanded internationally

44:17 How Kris changed as a leader

49:24 The advisor network that became a cheat code

51:42 Wrap up and how to connect

ABOUT KRIS RUDEEGRAAP

Kris Rudeegraap is the Co-Founder and CEO of Sendoso, an AI-powered sending platform helping B2B companies create meaningful engagement through personalized gifts, swag, and eGifts. He founded the company after recognizing a gap in how sales and marketing teams build real connections, drawing from over a decade in software sales.

Under his leadership, Sendoso has scaled globally with strong venture backing, driven by his belief that authentic, personalized experiences win in a digital-first world.

You can reach out to Kris through:

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

Website: https://www.sendoso.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.

From building a booming business overseas to being forced to start over, this is the founder journey most people never talk about.

James Rose built and scaled an online furniture company during a massive property boom in Eastern Europe—only to see it nearly collapse during the global financial crisis. After years as an entrepreneur, he was forced to swallow his pride, re-enter the job market, and rebuild through sales and leadership roles.

In this episode, James shares the unfiltered reality of going from founder to employee—and back again. He breaks down how sales became his lifeline, why founders delay exit planning, and how those lessons led him to build Inflectiv Group, a platform acquiring and rolling up profitable, founder-led agencies.

If you’re a founder thinking about scale, resilience, or engineering a meaningful exit, this conversation delivers clarity without the hype.

What you’ll learn in this episode:

• Why most founders avoid the reality check needed to plan a real exit

• How losing a business reshapes your view of risk, pride, and employability

• Why sales is one of the fastest paths to rebuilding after a setback

• The biggest mistakes founders make when fundraising or delaying M&A

• How minority roll-ups unlock value for founder-led service businesses

• What acquirers actually look for in profitable agencies today

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+105&utm_campaign=%24100M+Exits⁠

Get the latest fundraising insights, news, and tips:⁠https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+105&utm_campaign=%24100M+Exits⁠

Here's what you're in for:00:00 Introduction and Guest Welcome00:17 James Rose’s First Business Venture02:07 The Impact of the Global Financial Crisis04:09 Transitioning From Founder to Employee11:21 Re-entering Entrepreneurship Through M&A15:29 Market Trends and Acquisition Strategies29:58 Advice for Founders on Valuation and Exits36:35 Where to Learn More About James

ABOUT JAMES ROSE

He is the founder and CEO of Inflectiv Group, an investment firm backing independent marketing and communications agencies through minority investments, growth capital, and strategic support—while allowing founders to retain autonomy and control.

A serial entrepreneur, investor, and growth leader, James brings over 20 years of experience across media, technology, and M&A. He has created significant shareholder value in private equity–backed businesses by scaling revenue from £0.5M to £7M+ and building effective go-to-market strategies.

He has also worked closely with product and development teams to commercialize innovative SaaS offerings, bridging product vision and market execution. Today, James applies this hands-on experience to helping agency founders scale sustainably through disciplined growth and smart capital partnerships.

You can reach out to James through:LinkedIn: https://www.linkedin.com/in/jamesroseequitypartners/⁠Website: ⁠https://www.inflectivgroup.com/⁠

ABOUT JASON KIRBY

Co-founder of Thunder, a tech-enabled investment bank helping founders achieve ideal outcomes through capital strategy and M&A.

A serial entrepreneur with four exits, Jason has decades of experience in fundraising, M&A, and business building. He has coached hundreds of founders and transacted over $135M personally, with Thunder exceeding $200M+ in completed transactions.

You can reach out to Jason through:
Email: [email protected]
LinkedIn: ⁠https://www.linkedin.com/in/jasonrkirby/⁠

ABOUT $100M EXITS

The goal of $100M Exits is simple: equip founders with the knowledge and guidance to navigate capital strategy by learning from founders and investors who’ve already done it.

For some, the dream is a $100M+ exit. For others, it’s cash flow or IPO. Founders doing over $5M in revenue will benefit most from this podcast.
Be sure to subscribe—and let me know who you want interviewed next.