Over the past decade, I've built three multimillion-dollar businesses while growing a family and raising four children.

I started with no resources, no connections, and didn’t have access to the playbooks that would have made the journey 10X easier. 

As a kid, I made money garden landscaping for families at church, manufacturing merchandise for private clubs, and then developing websites and running ad campaigns for local companies.

By 21, I was founding companies. In the decade since, I've:

➤ Generated $300M+ in revenue
➤ Built operations in 1,000+ U.S. cities
➤ Served over 3 million customers globally
➤ Helped grow hundreds of small businesses
➤ Raised $30M+ in capital from Angels, VCs, Private Equity, and Family Offices
➤ Successfully navigated both successful and failed multimillion-dollar acquisitions
➤ Been featured in leading publications like Forbes, Bloomberg, Entrepreneur, USA Today and more
➤ Worked with and advised the world's most iconic brands, including Diageo, Mars, Tesco, 7-Eleven, AB-InBev, Molson Coors, and Constellation

BUT, the journey was hard (harder than it needed to be).

I’ve faced many of the things you don't think about when starting a company:

→ Fought off (and won) predatory lawsuits
→ Closed a Seed round days after my wedding
→ Negotiated with demanding government agencies
→ Worked with lobbyists to introduce or change legislation
→ Raised a Series A while in the hospital for my first son's birth
→ Navigated a failed multi-million dollar merger while my daughter was born
→ Survived near-extinction events where we had single-digit weeks or days to save the company

Personal interests: Boxing, strength training, being in the ocean, spending quality time with my wife Danielle and our four little ones.

———

👋 Follow me for daily tips on mindset, systems, lifestyle design, and high-growth habits.

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Chris Vaughn

I’ve loved investing since I was 13, when I bought my first stock, Apple, and realized you could actually own a piece of a company and participate in the upside.

In high school, I became one of the youngest interns at Morgan Stanley, where I studied under a financial advisor and learned how capital really moves.

Later, while working in strategy consulting and at a startup, I began angel investing on the side and quickly saw the power of getting in early and backing founders before the rest of the market catches on.

I have run a $25M fund and grown my personal portfolio to over 100+ companies including SpaceX, Anduril, Beehiiv, Kraken, and more. 

I now lead a frontier tech syndicate with a focus on space, robotics, and AI.

Elana Gold

Sam Altman says something that makes founders uncomfortable...

Most startups don't fail. 
They quit too early to ever work.

In YC office hours and interviews, Altman keeps pointing to the same mistake.

Founders are usually right about what they want to build.
They are almost always wrong about how fast it should start working.

What founders expect:
- Momentum early
- Clear validation
- Signals that feel obvious

What actually happens:
- Progress is slow
- Feedback is messy
- Nothing compounds on the timeline they imagined

That gap is where most startups disappear.

Altman has explained that early signals are some of the most misleading data points in a company's life. Early users are not representative. Early growth is noisy. Early feedback often points in the wrong direction.

Founders see this and assume something is broken.

Most of the time, it is not broken.
It is unfinished.

The common failure mode is not being wrong.
It is confusing slowness with failure.

Altman is not arguing for blind persistence or ignoring reality.

He is warning that many founders quit or pivot before the timeline they expected was ever realistic.

Early slowness is normal.
Confusion is normal.
Feeling behind is normal.

What is rare is staying long enough for the work to compound.

That is why most startups do not fail in dramatic explosions.

They fade out quietly when founders confuse
"this is taking longer than I expected"
with
"this will never work."

Those two things are not the same.

And confusing them is one of the most expensive mistakes a founder can make.

Partner at Red Beard Ventures | VC & Angel Investor

The 6-month MVP is dead. I just built one in a few hours.

Here's what I did…

I had an idea stuck in my head for months. There's no easy way to build a company data room. Most founders just use a messy Google Drive link - no clean interface, no tracking, no way to know if investors even opened it.

So I opened Lovable and started building.

I called it DataRoomIQ.

It does what founders actually need:
- Starts with ready-made templates from Pre-Seed to Series A
- Creates a professional front-end for your raise
- Enables you to see exactly who viewed your deck, when, and for how long
- Lets investors ask questions - AI answers instantly from your docs

A few hours later, I had an MVP.

A week later, I have a working product with pricing, templates, and a live example data room.

No developer. No coding experience. No six-month search for a technical co-founder.

I just built it.

This isn't just for solo founders anymore.

Product teams at Klarna, Uber, and Deutsche Telekom are already using Lovable.

The old way at big companies:
- Whiteboard and design for hours
- Bring in engineering weeks later
- Build a prototype over months
- Finally test with customers

The new way: 
- design and build on Lovable. 
- test it with customers instantly. 
- iterate live.

Pick your features. Build the prototype. Get real feedback. All during the same session.

The gap between idea and product used to be months.

Now it's hours.

Founders can validate before they fundraise. Product teams can test before they commit engineering resources.

I’m now sharing DataRoomIQ with founders and seeing them actually use it to replace messy folders with structured, investor-ready rooms.

The barrier to building used to be code.

Now it's just whether your idea is worth building.

What idea have you been sitting on that you could test this week?
#lovablepartner

Brand partnership • Partner at Red Beard Ventures | VC & Angel Investor

Early employees were sold a simple deal.

Join the startup.
Take less cash.
Give it 5 to 7 years.
Liquidity comes at the exit.

That deal no longer holds.

Take SpaceX.

World changing company. Tens of billions in value.

But they are still private after two decades.

Early employees didn’t lose conviction. They just ran out of patience.

So SpaceX has repeatedly allowed employee liquidity through secondary sales and tender offers, not as a bearish signal, but as pressure relief.

That’s the new normal.

The best companies are staying private longer.
Exits are slower.
Paper gains stopped feeling real.

Liquidity didn’t disappear. It moved to secondaries.

I break down why this matters for employees, angels, and investors in this week’s Cap Table 👇

Welcome back to The Cap Table Newsletter! This bi-weekly newsletter shares key insights on angel investing, start-ups, and investment opportunities. T

Open article: Why Secondaries Are So Attractive Right Now by Elana Gold • 5 min read

Why Secondaries Are So Attractive Right Now

Venture is back.

But not in the way most people think.

2025 looked like a comeback year on the surface: $469B deployed globally, the highest level since 2022. Headlines screamed recovery.

Underneath, the market quietly rewired itself.

Capital concentrated harder than ever.

Total deal count fell 17%, but mega rounds exploded. Fewer companies raised. The same companies raised again and again. 65% of all global venture dollars went into just 738 rounds.

Bigger checks. Fewer winners.

And almost all of it flowed to one place.

US startups captured ~70% of global funding. Europe and Asia grew modestly, but neither benefited meaningfully from the AI surge.

AI didn't just win. It absorbed the market.

AI companies raised $226B in 2025. Six rounds alone accounted for $111B.

This is not diversification. This is one macro bet.

If the winner-takes-most assumption holds, returns will be historic.

If it breaks, there are very few sectors left to cushion the fall.

Meanwhile, robotics quietly crossed a threshold.

$40.7B went into physical AI, the highest on record. Humanoids, autonomous systems, drones, foundation models.

Valuations moved faster than fundamentals. Some companies hit massive price tags without revenue or commercial proof.

And the smartest capital leaned into the concentration.

Top performing VC firms clustered almost all activity around AI agents, copilots, and infrastructure. A sharp departure from classic venture theory.

So what does this mean heading into 2026?

Venture did not broadly recover. It refocused.

Capital is available, but only if you fit a very specific narrative.
Scale matters more than ever.
Proof matters later than it probably should.

Are you betting on the concentration thesis? Or looking for what got left behind?

If your calendar is full and revenue is flat, this is probably why…

You're spending time on people who were never going to buy.

The bottleneck isn't effort. It's timing and signal.

Most founders treat every lead the same. But real buyers don't announce themselves. They research quietly, compare options, loop in teammates, and by the time they talk to you, they've already decided.

Here's what I'd do differently today.

Step 1: Stop guessing who's in market

Not "enterprise companies." Be specific.

"Series C+ fintechs with 200+ employees hiring a VP of Engineering."

Apollo AI Assistant prompt:
"Build my TAM using ICP filters and score accounts Bronze to Platinum."

You get a ranked list and clear reasoning for why each account fits.

Step 2: Identify the right people, not just accounts

Enterprise deals don't close with one person.

You need the people with budget, influence, and urgency.

Prompt:
"Find decision makers at these accounts and enrich their contact information."

No manual research. 

Step 3: Prioritize accounts showing real intent

This is where most founders waste time.

Pricing page visits. Product deep dives. Relevant role changes.

Prompt:
"Show me accounts visiting my pricing page or engaging with high intent pages."

Step 4: Let workflows handle the follow-up

When intent shows up, speed matters.

Prompt:
"Create a workflow that moves high intent accounts into an active sequence."

No manual follow-up is needed. 

This is why I partnered with Apollo.

The AI Assistant doesn't help you send more messages. It helps you stop wasting time on the wrong ones.

For founders, that's the difference between being busy and building revenue.

#ApolloAIAssistant #ApolloPartner

Last year I was taking 12+ calls a day.

But... I was drowning.

Hearing pitches, spending time with portfolio companies, growing my network, helping to fundraise, and running the syndicate.

I would eat during calls. Run to the bathroom if I was lucky enough that one ended early.

All while trying to listen, think, and take notes at the same time.

I told myself that taking notes helped me pay attention.
In reality, I was half present, trying to type and ask questions.

A week later, during our investment call meeting, my partner would ask follow-up questions:

- What valuation was their last round at?
- What did they say about last year's product launch?
- How much revenue were they projecting for this quarter?

I'd scroll through my notes, hoping they were right.
Trying to decode half-sentences I barely remembered writing.
Realizing my notes were not clear but they were my only source of truth.

And that was the problem.

One day, we decided to try an AI notetaker.

I was skeptical. I assumed outsourcing notes would make me less engaged.

What actually happened was the opposite.

I stopped typing.
I listened more closely.
I asked better questions.

And instead of relying on my memory or messy bullet points, I could go back and ask real questions later and get real answers.

That's when Otter.ai started to feel less like a productivity tool and more like infrastructure.

Now every call is searchable. Every detail is saved. And when my partner asks about a conversation from three weeks ago, I pull up the exact quote in seconds.

I still take meetings all day.

I just stopped pretending my brain and sloppy notes were enough.
#OtterPartner

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