NOT NO
- timoneil549
- Jul 3
- 6 min read
A Founder’s Guide to Surviving Investor Rejection—and What It Taught Me
By Timothy S. O’Neil
Introduction
One of my favorite movie scenes comes from Volunteers.
Tom Hanks is trying to negotiate with a local warlord. Standing nearby is the warlord’s beautiful bodyguard—whose command of English is somewhere between nonexistent and interpretive dance. Tom flashes a grin that suggests he’d be perfectly happy if she happened to be part of the bargain.
The warlord responds with something to the effect of, “If I say yes… and not no…”
I honestly don’t remember exactly how the scene ended.
What I remember is what popped into my own head.
I’d settle for not no.
At the time it was just a funny line.
Thirty years later, after more investor meetings than I care to count, I finally understand why it stuck with me.
Founders spend years chasing “yes.”
Investors rarely give you one.
Instead they say…
“Interesting.”
“Come back after revenue.”
“Let’s reconnect in six months.”
“We’d like to see your next release.”
“Keep us posted.”
None of those are yes.
But they aren’t no.
If you’re building a company, you eventually realize that companies aren’t built on yes.
They’re built on not no.
The High Wire
Being a founder is the proverbial high-wire act.
There’s no safety net.
No guarantee.
No instruction manual.
One minute you’re convinced you’re about to change the world.
The next minute you’re looking at your checking account wondering whether the bank has confused you with someone who’s actually employed.
People love talking about entrepreneurial risk.
Let me save you some time.
It’s all risky.
The right decisions.
The wrong decisions.
The crazy decisions.
Sometimes you don’t know which one you made until two years later.
Then there are the mornings.
Three o’clock.
Every.
Single.
Morning.
Not because the alarm went off.
Because your brain did.
There’s always one more investor to research.
One more slide to improve.
One more grant proposal to edit.
One more feature to design.
One more email to send before the day job begins.
People think founders work eighty-hour weeks.
The truth is…
founders never really stop working.
The company follows you to bed.
It wakes up before you do.
And then there’s that feeling.
If you’ve ever built a company, you know exactly what I’m talking about.
That knot in the pit of your stomach.
It never completely goes away.
It’s there when you wake up.
It’s there during investor meetings.
It’s there while you’re brushing your teeth.
It whispers the same questions over and over.
What did I forget?
Are we going to make it?
Am I asking my family to believe in something impossible?
Is this the dumbest thing I’ve ever done… or the smartest?
I’ve come to think of it as the founder’s tax.
Nobody talks about it.
Everybody pays it.
Some people call it stress.
Founders call it Tuesday.
One of my favorite startup metaphors comes from Silicon Valley.
Ron LaFlamme, the eccentric attorney, explains venture capital using sea turtles.
Sea turtles lay hundreds of eggs because only one or two eventually make it to the ocean.
"That's what Peter Gregory is doing," Ron explains. "Making sure one or two of his compression plays make it to the sea."
The first time I heard that I remember thinking,
"Why not just pick stronger turtles?"
Of course, that's not how venture capital works.
They're playing portfolio math.
Fund enough companies and one eventually becomes the next Google.
They're not looking for certainty.
They're looking for outliers.
Founders don't have that luxury.
Most of us get one turtle.
One company.
One dream.
One shot.
It's amazing how differently you look at risk when you're carrying your only turtle.
If raising venture capital is a marathon...
government grants are an ultramarathon.
Uphill.
Into the wind.
Dragging a filing cabinet behind you.
You spend six weeks writing.
Three weeks editing.
Two weeks wondering whether Requirement 3.2.17(b) means exactly what you think it means.
You finally hit "Submit."
Then...
absolutely nothing.
Weeks become months.
Months become more months.
Eventually an email arrives.
Your pulse quickens.
Your palms get sweaty.
You open it.
"Thank you for your interest..."
That's government-speak for, "Better luck next time."
The amazing part?
You immediately start writing the next proposal.
Founders are funny that way.
The government didn't invent persistence.
Entrepreneurs did.
I actually like accelerators.
Some of them.
Many provide genuine value.
They introduce founders to investors.
They surround you with experienced entrepreneurs.
They shorten the learning curve.
Some absolutely earn the equity they receive.
Others...
Well...
Let's just say the first image that came to my mind was a skinny kid explaining proper deadlifting technique to a professional bodybuilder.
It made me laugh.
Mostly because I've been there.
Now before anyone gets offended...
No, I don't know everything.
Far from it.
But this ain't Marine Corps boot camp.
I don't need somebody teaching me how to polish my boots.
I've spent decades leading soldiers, briefing executives, running cybersecurity organizations, and solving difficult problems.
Teach me something I don't know.
Introduce me to someone I couldn't otherwise meet.
Open a door that's been closed.
Challenge my assumptions.
That's acceleration.
Teaching me how to center a title on a PowerPoint slide?
Not so much.
Now, to be fair, they usually introduce you to investors.
Of course, they don't do it out of the goodness of their hearts.
They generally take a slice of your company.
Sometimes it's a reasonable slice.
Sometimes...
It’s a fat butcher's slice.
Every founder has to answer the same question.
Was it worth it?
If the answer is yes...
great.
If not...
that was one expensive PowerPoint lesson.
Somewhere along this journey I stopped looking at my investment portfolio as retirement.
I see software development.
Advertising.
Patent attorneys.
Trade shows.
Cloud hosting.
Developers.
My financial advisor sees diversification.
I see operating capital.
Retirement?
I'll think about retirement after Version 5.0 ships.
Every now and then I tell Suzanne we're flying first class to the Maldives for a week of scuba diving.
Just as soon as...
well...
just as soon as we can afford a Margarita machine.
Fans of Silicon Valley will appreciate that reference.
Everyone else probably thinks I've developed an unhealthy obsession with frozen drinks.
They're not entirely wrong.
The funny thing about founders is that we stop measuring wealth the way everyone else does.
A new car?
That's six months of development.
Kitchen remodel?
Marketing budget.
Vacation?
Another developer.
People ask how founders keep funding their companies.
Simple.
We stop thinking about assets.
We start thinking about runway.
People ask what it's like to build a company with my wife.
The answer usually surprises them.
We work remarkably well together.
Mostly because we work remarkably well apart.
Ron LaFlamme would probably describe us as yin and yang.
That's us.
I'm the dreamer.
Suzanne is the realist.
I see possibilities.
She sees details.
I chase ideas.
She quietly points out the seventeen reasons one of them probably won't work.
She's usually right.
Long before software, we bought a short-term rental.
The number one comment from our guests wasn't the location.
It wasn't the view.
It wasn't the amenities.
It was one word.
"Immaculate."
That's Suzanne.
If NASA hired her, astronauts would dust the launch pad before liftoff.
She has standards that make hotel inspectors nervous.
Thank goodness.
Somebody has to.
Every founder needs someone willing to ask,
"Are you sure?"
Not because they doubt the dream.
Because they want the dream to survive.
People celebrate founders.
They should spend more time celebrating the people who quietly make founders better.
There's an old saying.
"If you see a turtle on a fence post, you know it didn't get there by itself."
How he got up there is anybody's guess.
Yes...
I'm mixing metaphors.
It's my article.
Besides, if you've ever started a company, you know reality stopped making sense a long time ago.
You stop measuring life normally.
Your retirement account becomes software development.
Vacation becomes cloud hosting.
Credit cards become temporary venture capital.
Your dog starts recognizing the Amazon delivery driver by first name.
Normal people call this insanity.
Founders call it product-market fit.
The truth is, nobody builds a company alone.
Somebody always believed.
Somebody always introduced you to someone.
Somebody always opened a door.
And if you're lucky enough to succeed...
maybe someday you'll become the person holding the door open for the next founder trying to get through.
That's a legacy too.
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