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Tough founder questions: I got punched in the mouth, now what?

If you are a founder, you know the feeling.

Tough founder questions: I got punched in the mouth, now what?
[LIGHTFIELD STUDIOS/Adobe Stock]

Mike Tyson said it best: “Everyone has a plan, until they get punched in the mouth.” It’s going to happen to you eventually. Tyson did a follow-up interview about that quote and said, “If you’re good and your plan is working, somewhere during the duration of that, the outcome of that event you’re involved in, you’re going to get the wrath, the bad end of the stick. Let’s see how you deal with it. Normally people don’t deal with it that well.”

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If you are a founder, there is an almost inevitable moment when you feel like you’ve been punched in the mouth and then have to deal with the wrath, the bad end of the stick. I can tell you with 100% certainty that it’s terrifying. Some punches hurt more than others, but they all add up—and while entrepreneurship many times looks like rainbows and sunshine from the outside looking in, the teams that are grinding it out on the inside are all in different rounds of a Mike Tyson fight. The proverbial punch in the mouth comes in many forms:

• Your first-ever CTO that you’ve been telling everyone about quits and leaves you high and dry.

• You almost run out of money because fundraising takes way longer than you thought.

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• You find out you don’t have enough storage capacity for your website and your whole system could crash.

• One of your key investors says they are going to also back another company that might not be a direct competitor today, but will inevitably be in the future.

• Your biggest customer says they are going to leave if they don’t get a laundry list of features built for them (which of course will take your whole engineering team and more).

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So what happens when, almost inevitably, something doesn’t work as planned? What do you do when the bad side of entrepreneurship lands a big punch to the mouth?

In my experience (yes, all those things above happened to me, and many, many more) you likely do not have many people you can discuss these issues with immediately. You can’t talk to your team because they could lose confidence in you (and you’re already losing confidence in you). You likely can’t talk to your biggest investors (even if they say “Tell me everything”) because they might start thinking “Hmmm, I wonder if we should cut our losses here?” And you likely can’t talk to your friends and family because you have likely been the topic of most family dinners and happy hours with friends talking about you chasing your dream and starting this amazing business.

You need to get other fighters in your corner. You need people who have already been punched in the mouth (ideally lots of times) and made it through successfully. You need a “corner committee” of trusted people who have these three characteristics:

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1. They have your back but are also incentivized for the business to work well (not just make you happy).

2. They are not afraid to tell you the cold, hard truth, even when it’s definitely what you don’t want to hear. Bonus points for grounded optimists—not “inflate your ego” optimism, but people who help you see the light through the tunnel.

3. Most importantly, they have been through this before (and have felt the punch in the mouth). Other entrepreneurs who are a few steps ahead of you or have recently been through the entrepreneurial journey are ideal.

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Go to these people with these feelings in your gut early and often and work through them together. Get multiple points of view and triangulate the conversations to reach a conclusion that makes you feel whole. You’ll know it when you feel it and they can help you get there. Get these people in your corner as early as you can in your entrepreneurial journey and they will help coach you through the inevitable punch in the mouth.


Riggs Kubiak is an Entrepreneur in Residence at Procore Technologies, supporting CEOs & Founders in the ConTech and PropTech ecosystems to accelerate growth

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