I'm a serial entrepreneur who has raised $145M+ and has had multiple exits. I'm now on a mission to support founders with their capital strategy and acquire the capital they need to grow their businesses. Thunder.vc is a tech-enabled investment bank for founders, by founders. 

When it comes to supporting the founders in our Thunder.vc community, here are some free resources that can help you with your capital-raising efforts. 
- $100M Exits newsletter & Podcast 
- Sign up at http://blog.thunder.vc 
- Free list of AI-recommended VCs specific to your business - https://web.thunder.vc/list-of-investors-vcs-for-founders  
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Securities are offered through Finalis Securities LLC Member FINRA / SIPC. Thunder X Capital, LLC is not a registered broker-dealer, and Finalis Securities LLC and Thunder X Capital, LLC are separate, unaffiliated entities.

Jason Kirby

This is the story most founders never post on LinkedIn. Most founders only focus on the upside.
 
Very few imagine the moment they stop being CEO.

James Rose scaled his first business to millions in revenue rapidly. Everything was going up and to the right...until it wasn't anymore.

Then the market turned.
The business collapsed.

And suddenly, he had to do the unthinkable: become an employee again.
Not because he wanted to. Because he had to. Family to support, lifestyle to maintain, and unsure of what the next big idea would be. 

That transition of losing the company and the identity was harder than the failure itself.

I chose to have James on because he had some amazing insights around this transition. It took him over a decade to get back in the saddle as a founder again, but he's managed just fine. His life wasn't over. 

But he was practically unemployable outside of sales. He was "over qualified"

So he dropped his ego and aspiration for a VP role and took a mid level sales job and grinded. It was tough, but it worked for him.

In this episode of $100M Exits, James breaks down:

- The emotional toll founders don’t talk about
- Why identity gets dangerously tied to the title
- How this moment reshaped how he builds today

I felt this was an important story to share as most founder don't know what's next after a failure. James's story is a ray of hope for the hopeless founder wondering what to do next. 

See the full episode in the article.

4x Exits, $100M+ Raised. Helping founders raise/exit with clarity, control, and conviction.

Watch the full video here This is not a story we discuss often on this podcast, but I felt Jame's story of having to "get a job" after scaling a multi

Open article: From CEO to employee, the pivot no one prepares for by Jason Kirby • 2 min read

From CEO to employee, the pivot no one prepares for

Yesterday I spoke my partner Oliver Low about a founder who just lost 2/3rds of their revenue right before making an acquisition. 

It was a total death to the founder. In their mind, how could they, in good faith (and legally) acquire a company with their stock if they just had a massive hit like that. 

This roll up acquisition strategy was designed by my partner and I to help them clear their pref stack and ensure the founders had a solid paid day for their efforts.

No one expected their anchor client to change management and drop the contract 🤯 

We empathized with the founder, and they ultimately just want to throw in the towel, wind down the company and return the $0.25 on the dollar back to their investors. 

I honestly respected them for that. They've had it hard enough on their journey, to reboot after a hit like that and all their plans crumble before their eyes...could they really put in another 5+ years to turn it around and clear their pref stack...is it even worth it?

Sometimes it's just better to quit...yes...the nasty Q word. We're often don't as founders "never give up" "never quit"

But sometimes, it's economically illogical to keep going from their perspective. 

The company needs a recap to ditch their toxic cap table that's holding them back, raise more cash or sell to someone who has cash to perform the AI roll up strategy. But the founders don't the energy or the desire to put up that fight.

It's a great business otherwise, just the prefstack makes it not worth it. 

It's a reality that more and more founders are running into when they can't grow fast enough to exceed their past valuations or pref stacks. 

If you know founders facing these issues, tag them in the comments and let them know they're not alone. 

I spend my days helping founders navigate these situations. 

For this particular founder, I might acquire the business myself and put in a CEO to execute the roll up strategy. There's always a creative way to solve every problem, but the incentive has to be there to make the juice worth the squeeze...never forget that part.

If your CAC is rising, your only defense is LTV.
Brian Ree built one of the highest-LTV businesses in fashion & sold for $700M

Here’s the playbook that led to a ~$700M outcome:

- Make LTV your North Star (not revenue).
- Improve gross profit per order before scaling traffic.
- Control supply chain via private label.
- Track 52-week cohort spend religiously.
- Use AI to predict product-level expected value.
- Optimize retention before increasing paid spend.

My takeaway from Brian, especially in the world of DTC today, growth doesn’t fix broken unit economics. It magnifies them.

While competitors chased top-line revenue, DailyLook engineered durability.
The result? Stronger margins, better retention, strategic leverage in M&A.

Watch the full episode below.

Watch the full video here Brian Ree’s journey with DailyLook is a reminder that survival precedes scale. When growth stalled and capital dried up, he 

Open article: How Brian Ree Turned a DTC Crisis Into a $700M Exit to Victoria's Secret by Jason Kirby • 2 min read

How Brian Ree Turned a DTC Crisis Into a $700M Exit to Victoria's Secret

When Kris Rudeegraap raised $100M from SoftBank for Sendoso, it didn’t start with a term sheet.

It started with a coffee.

SoftBank came inbound in late 2021.

Within days, that coffee turned into partner pitches.

Two weeks later, he was told:

“Block your entire calendar. We’ll tell you the day before Masa is ready.”
No private jet to Japan, like he was told, just a Zoom grid with a dozen SoftBank partners and Masa Son at the center.

Masa wasn’t casual.

He knew the numbers.

He asked pointed questions about growth velocity.
He grilled the US partners about how big this could get.

Then: silence.

A couple weeks later, Kris got the term sheet.

But the wire? Delayed for months...MONTHS because of international transfer reviews.

But once that $100M was real, expectations changed overnight.

Not subtly. Overnight.
At the time, Sendoso was around ~$50M ARR.

They had already raised roughly $65M prior.

With $165M+ in preferred capital stacked, the thinking wasn’t defensive.
It was:

“How fast can we double again?”

So what did they do?
They hired. Aggressively.

Kris said they ramped up to roughly 30 recruiters just to fuel hiring across go-to-market.
SDRs. AEs. Marketing. Post-sales support.

Because in 2021, the math felt simple:
More heads = more revenue.

Top-down target said “double.” Bottoms-up math didn’t get them there. So they changed the inputs. Turn on the hiring flywheel.

In hindsight, that wasn’t irrational, but tt was consistent with the rest of the market raising stacks of cash.

But then 2022 hit.

And the same company, with the same strategy, suddenly had to pivot. Growth at all costs pivoted to conserve and generate profit. He hired all those people and before they could generate a dollar of revenue, he had to lay them all off 😬 

The board conversations change when capital isn’t cheap anymore.
Which leads to two uncomfortable truths:

1️⃣ Mega-rounds distort decision-making
When you have $100M in the bank, the pressure to justify it shapes behavior. You optimize for scale, not resilience.

2️⃣ Capital amplifies strategy, it doesn’t fix it. If your go-to-market motion works, capital accelerates it. If it’s fragile, capital magnifies the fragility.

I talk to founders everyday wanting to raise capital, but they often don't realize the burden that comes with it. 

But kudos to Kris, he took the medicine, built an advisory board of over 100 experts, and navigated the storm to acheive amazing results being a leader in his category. 

If you want to hear the full story, check out my latest podcast on $100M Exits.

Watch the full video here Raising $100M doesn’t solve your problems; it magnifies them. Kris shares what founders rarely talk about: the operational w

Open article: How Sendoso Raised $100M From SoftBank by Jason Kirby • 2 min read

What color box are you in? 

If you're not in the green at the very least...I don't think we can be friends. 

I'm in the redbox  🦞 

This also explains the mega valuations we're seeing in AI. Real revenue is being generated at a scale and speed never seen before, and we're barely scratching the surface.

Founder & CEO of Sellible.ai, an AI-powered sales enablement platform helping B2B teams simulate, analyze, and perfect their pitch. We combine real-time roleplay with personalized feedback to drive sales performance - replacing outdated sales training with AI-native solutions.

With 15+ years in tech and over a decade in AI, I’ve led high-performing engineering teams across both Wall Street and venture backed startups. My career includes pivotal roles at Goldman Sachs, JP Morgan, and Morgan Stanley, where I drove large-scale innovation in Investment Banking technology.

I’ve co-founded and scaled multiple ventures, including FLYX (Best App – Google Play 2020), Bakstage.AI (AI-powered video sales for B2B), and head engineering at FX HedgePool, which was later acquired by LMAX Group. I hold patents in encryption and web security, and have been recognized as a Top 10 CTO by Entrepreneur Magazine and a Top 50 Tech Professional by OnCon Awards.

Outside of building, I mentor startups, speak at industry events, and contribute to founder communities on AI, product strategy, and scaling engineering orgs.

Learn more about what I'm building at sellible.ai

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jason Kirby's LinkedIn Performance

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