In Entrepreneurship, Puzzling Out A Solution Not That Easy

By Neil Senturia
The San Diego Union-Tribune

WWR Article Summary (tl;dr) Serial entrepreneur Neil Senturia shares some of the pitfalls that “second-time founders” tend to make.

San Diego

Problems to solve. No shortage.

And, of course there are solutions. But the key piece of the puzzle is to figure out the order of events necessary to create a solution.

This is not as easy as it sounds because everything is connected. You are confronted by the “if — then” puzzle. The decision tree has many branches.

So which limb do we work on first?

You have a chain saw; now find an expert arborist. In my own case, I am starting a new adventure, and I was sure I knew exactly how to do it (serial entrepreneur, after all). I was positive that it should be a 501C-3, non-profit.

Three hours of conversation later with two community foundation CEOs and two conversations with what are called “fiscal sponsors,” and it was clear that I had the wrong structure. In other words, at the beginning I was certain — and I was certainly wrong.

The key to my puzzle was figuring out who was the customer and how could this idea, (trying to decrease recidivism among formerly incarcerated) scale.

Since everyone needs a mentor, I turned to a recent article by James Currier, managing partner at NFX ventures, checked my ego at the door and reviewed the pitfalls that “second-time founders” tend to make.

Currier lists overconfidence as mistake numero uno. If you are a “been there, done that” founder/CEO, you can easily fall into the trap of feeling entitled and “becoming superficial.”

The next one on his list is “not asking stupid questions.” That goes back to the order of solutions. Are you sure that you need to build it yourself, or does an elegant solution (that you were not aware of) exist and that will save you time and money?

Another is “surrounding yourself with sycophants.
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” This one is complex, because you want pushback and questioning, but you also don’t want to trade a yes-man for a jerk. This argues for working with people you previously know and trust — after all, you are a second-time founder, so one measure of your ability is to see if the gang will come back and work with you again.

One of my favorite companies, Mercato, has a CEO who has been able to bring the same core six people with him each time from his previous companies. (Maybe he is piping in ether at the Monday management meetings).

“Too much money too soon.” Currier reminds all of us that getting the dough is not the same as building “the culture, the team, the cadence or the processes.” I worry about my second-time founders developing arrogance and certainty without seeing the cliff they are about to ski over.

Luck. This is my all-time favorite. Currier suggests that your first success may have been a “cascade of miracles.” I have written previously about pulling rabbits out of hats (it works best when you put the rabbit in the hat in advance). Don’t ever discount good fortune, but you still did it, so be careful to avoid the imposter syndrome.

Impatience. You must still be rigorous about dumping a second-rate idea early. I have railed frequently at founders who are unwilling to acknowledge that the dog is dead. Continuing to buy dog food is a waste of money.

Impact. Our second-time founder wants to not only knock it out of the park financially, but also wants to create massive impact, change the world stuff.

The risk is you get focused primarily on impact and forget about the customer. (I will try to remember this as I focus on my favorite felon project.)

And now, the killer risk. You ignore the need for “founder-market fit.” You start the project because you think you could make a lot of money, or it’s a good idea and you like the guy, or someone offers you money that is burning a hole in their pocket.

But unless there is a compelling “fit,” meaning the combination of domain expertise, passion, founder story, personality, partners and vision, then the risk of losing interest, as well as losing money, becomes exponentially higher.

And finally, don’t do any deal in order to prove something to someone. “That is a tale told by an idiot, full of sound and fury, signifying nothing” — Macbeth

Rule No. 667: Deals come and go, choose wisely.

Source: From Neil Senturia’s book “I’m There for You, Baby: The Entrepreneur’s Guide to the Galaxy,” which has more than 200 rules for entrepreneurs (
Distributed by Tribune Content Agency, LLC.

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