Will our startup get funding? We face a critical moment as founders

When we last met Pauline, she was tied to the tracks, and the lonesome whistle was blowing ever closer.

I remember a famous poetic exchange between a young college student and his father. The telegram:

And the midwestern father responded.

Some entrepreneurial teachable moments come up here. We all know about “sunk costs,” and the temptation to continue down the road of ruin, hoping that, just around the corner, the light will shine. After all, we are so close, we have already spent a lot of money, and if we just hang on another day or two, the new deal will close. I mean you can’t just toss in the towel. (Unless you happen to own a laundry with extra towels).

However, let’s also spend a minute on another of my favorite subjects – Texas Hold ‘Em. If you do not know the game, look it up. The question for every gambler is should you pay up to see the “river card.” The river card is the last card turned up, and it makes or breaks lots of hands.

After all, you already have money in the pot, and you weigh sunk costs with the cost to see that last card, the one that fills the inside straight. I have a fishing buddy, a lifetime gambler. He tells me to think very carefully about the “cost” to see that card. Live to play another day or take the bus home.

May 11: The team meeting. Bravado and fantasies. We are indomitable. No venture capital money, so what, we will cobble together a few nickels from the original investors and pay up to see that card. A big customer has just signed and greatness lurks.

May 14: Reality. Finally. The soup kitchen has closed. We are done. We could not raise enough money. We will sell our banjo picks to anyone who has a banjo. You get picks, sheet music and an amplifier.

Now, let me be clear. This is painful. It hurts to fail. Lives are being upended. Even with kindness and severance and decency, it still is painful for everyone. But this outcome is not unique. We are one of a thousand startups that come up short. That is the game you signed up for.

You may remember that fellow going down the Amazon. The one with the low-ball offer. I told you that you always need to be polite when saying no. And now frankly that offer is looking kind of interesting.

We are meeting for breakfast next week.

It is a little like putting a child up for adoption. Whatever the reason, you always hope that they will have a good home and a chance to grow up tall and straight.

But not every child finds a home, so I am deeply aware that our final chapter may end up gathering dust in a HubSpot drawer for failed dreams and nice tries.

Where is Elisabeth Kubler-Ross when you need her most? Denial, anger, bargaining, depression and acceptance. We are done with denial, we are dealing with anger, but bargaining – that is what comes next.

I have two suspects who might help us with a soft landing. But caution here. You do not have a lot of time. Clear focus, save the team first, software second and look for nickels last.

There will be ample opportunity to look back and consider. My nature is to do a little of that, but in general, a post-mortem often feels like crying over spilled milk. Just press on.

This is a critical moment for every founder. The inviolate rule is: Do not leave a mess. Get a mop and a rag. And do not look to distribute blame. They know, and you know, and nobody else needs to know.

As for my column, I am going to take a short break. I need some time to lick my wounds. I will be back in a few weeks to tell you how the movie ended. I am going to skip depression and go directly to acceptance.

Rule No. 549009454: Didn’t see that coming.

Senturia is a serial entrepreneur who invests in startups. Please email ideas to neil@askturing.ai