The key is basically to sell. "We're all simply burning time" but we're all talking about burning money. The old phrase Get Big or Get Niche or Get Out holds mostly true. If you can't Get Big (the asymmetric return) or Get Niche (hyper efficient & growing) then Sell or Merge. I frequently see two players making the market smaller by fighting hard against each other - the TAM get smaller (as prices come down) and sub divides again and again. Join forces. Or simply sell out and burn your time elsewhere. Your 3 years to a $3m disappointing exit with everyone pissed off could be the training rails for a 8 year $500m exit in your next gig. "We're all simply burning time"
We merged duedil with Artesian for exactly this reason and the founder of artesian led the combined entity and rebranded to Fullcirlc selling it to nCino a few years later. Fitted the merging scenario I mentioned about - combine forces, become a single vendor with a wider offering vs competing vendors driving the prices down. You accelerate as the combined entity and prices are held up or frequently increase
This is a great list. The last one resonates with me in particular. I've been in the company where the founder lacks the leadership and EQ skills needed to retain top talent and the company slowly loses their key players. It was painful. I wouldn't be who I am without that experience, though.
My dream is kestryledge.com can serve these companies and arm the teams and leaders with the tools needed to succeed.
A lot of startup failure gets narrated afterward in language that sounds noble, dramatic, or inevitable when the real damage was usually much more ordinary. Bad market understanding. Weak cash discipline. Confusing a prototype with a business. A founder who did not change as the company changed.
And sometimes, to make it worse, teams push out or ignore the people who keep raising the boring parts because those truths kill the fantasy. Not everything in startup life is nonstop innovation, velocity, and vision. Somebody still has to understand procurement, cash timing, margins, compliance, taxes, and the thousand unglamorous realities holding the structure up. A company can get very excited while quietly sidelining the people trying to keep it honest.
That is what makes this piece useful. It brings the spotlight back to the structural stuff people usually notice too late.
The line that stayed with me is the idea that most startups die because the boring bits were not taken seriously enough. That feels right, and probably more honest than a lot of the storytelling wrapped around failure after the fact.
Strong piece. Clear-eyed, unsentimental, and worth sitting with.
Thank you for the thoughtful comment, Mark. Yes, the book and compiling my thoughts for this piece have certainly helped clear out a few things in my head. Hindsight is always 20/20. 👓
The key is basically to sell. "We're all simply burning time" but we're all talking about burning money. The old phrase Get Big or Get Niche or Get Out holds mostly true. If you can't Get Big (the asymmetric return) or Get Niche (hyper efficient & growing) then Sell or Merge. I frequently see two players making the market smaller by fighting hard against each other - the TAM get smaller (as prices come down) and sub divides again and again. Join forces. Or simply sell out and burn your time elsewhere. Your 3 years to a $3m disappointing exit with everyone pissed off could be the training rails for a 8 year $500m exit in your next gig. "We're all simply burning time"
Any particular examples that come to mind, Chris?
I read The Profit Paradox last year and it was specifying going down a niche too, but didn’t have the VC lens like yours.
🔗 https://millennialmasters.net/p/profit-paradox-jan-eeckhout
We merged duedil with Artesian for exactly this reason and the founder of artesian led the combined entity and rebranded to Fullcirlc selling it to nCino a few years later. Fitted the merging scenario I mentioned about - combine forces, become a single vendor with a wider offering vs competing vendors driving the prices down. You accelerate as the combined entity and prices are held up or frequently increase
This is a great list. The last one resonates with me in particular. I've been in the company where the founder lacks the leadership and EQ skills needed to retain top talent and the company slowly loses their key players. It was painful. I wouldn't be who I am without that experience, though.
My dream is kestryledge.com can serve these companies and arm the teams and leaders with the tools needed to succeed.
Really solid breakdown
Startups rarely fail from surprises, but from overlooked fundamentals breaking down over time.
It’s one of those cases where time doesn’t heal everything, but it’s rather unforgiving.
Small missteps in focus, execution, or communication that go uncorrected long enough to compound.
The part about the founder not keeping up was on point 👊🏻🎤
A lot of startup failure gets narrated afterward in language that sounds noble, dramatic, or inevitable when the real damage was usually much more ordinary. Bad market understanding. Weak cash discipline. Confusing a prototype with a business. A founder who did not change as the company changed.
And sometimes, to make it worse, teams push out or ignore the people who keep raising the boring parts because those truths kill the fantasy. Not everything in startup life is nonstop innovation, velocity, and vision. Somebody still has to understand procurement, cash timing, margins, compliance, taxes, and the thousand unglamorous realities holding the structure up. A company can get very excited while quietly sidelining the people trying to keep it honest.
That is what makes this piece useful. It brings the spotlight back to the structural stuff people usually notice too late.
The line that stayed with me is the idea that most startups die because the boring bits were not taken seriously enough. That feels right, and probably more honest than a lot of the storytelling wrapped around failure after the fact.
Strong piece. Clear-eyed, unsentimental, and worth sitting with.
Thank you for the thoughtful comment, Mark. Yes, the book and compiling my thoughts for this piece have certainly helped clear out a few things in my head. Hindsight is always 20/20. 👓
It is but we can always learn and do better next time