Punchable Face

May 18, 2026 | Issue #135

This is a blog written by Kaustubh Deo // Guesswork Investing about acquiring & operating small businesses. If you are a new reader / new searcher, please start here.

---

You’ve likely heard someone remark about an annoying person: “Man, that guy has such a punchable face.”

But what about the inverse — who are the folks that have a knack for taking a hard punch to the face?

As I hear of difficulties faced by my fellow SMB owner peers, I’ve noticed that the strongest owners are all pretty damn good at being punched in the face.

Now, I’m not the end-all be-all opinion when it comes to what makes a successful entrepreneur. But as my friend Christian Ruf says, attributes matter.

And the longer I’ve been in this role, the stronger I feel that having a face that can take a good punch, or two, or twenty, is a key attribute of a decent small business owner.

Let’s be very clear; this is different than having thick skin. Having thick skin implies a layer of protection, like bad things can roll right off of you.

Getting punched in the face is different — you will, and should, feel the impact.

• It’s being told by a key employee that they’re quitting with no notice period.

• It’s the major vehicle accident that stops revenue for a crew and triples your auto insurance rates for the next year.

• It’s being served notice from a big customer that they are cancelling their contract and moving to a new provider.

The punch is painful on impact, when it breaks your nose. The reverberations of each punch will last for weeks and months to come as your broken nose heals. I’m still paying elevated auto premiums from a truck crash (part 1 & part 2) from a couple years ago.

So if you’re a searcher/prospective small business owner, the operative question here is: “Do I have a face that can take a good punch?”

Let’s discuss.

---

Sponsor Information

We’re proud to have Oberle Risk Strategies as our sponsor. Oberle is an insurance brokerage that specializes in serving search funds and acquisition entrepreneurs.

I’ve known and worked with them for 5+ years, so can confidently say they are the firm you can trust for insurance due diligence — this is not an area to overlook in your deal.

The service is fantastic, they give practical advice, and – the best part – their offering is free. Reach out to them by filling out the form here.

---

Can you take a punch?

There’s no objective litmus test here — it requires honest introspection.

But I’ve thought of a few questions to ask yourself:

1. When something goes wrong at work, is your first instinct to complain or avoid the issue, or is it to go into problem-solving mode?

2. How have you experienced pain or grief in the past? Do you have the emotional skills to process them rather than avoid them?

3. When things go wrong, how easily & quickly can you joke about them?

4. How does your particular flavor of anxiety (and we all have a flavor) manifest? Does it lead to analysis paralysis? Or does it lead to manic testing and experimenting to get ahead of potential issues? Business owners need more of the latter.

It’s obvious what the “right” answer is to each question if the goal is to say you have a punchable face i.e. if you want to feel more naturally inclined towards entrepreneurship.

But no one is checking your answers — this is for you, and you alone. If you can’t be honest at this stage and buy a business, you’ll learn the hard way later.

As I’ve spoken about in recent posts, a lot of career & life design comes down to selecting your hard. There are other hards that come with a standard W-2 corporate job.

But before looking at the benefits of entrepreneurship, honestly assess if you’re ready for the hard of being punched in the face everyday, smiling, and forging on.

---

A Human Anti-Depressant

Your team signed up for a job. Ideally, a stable job, with a steady paycheck, with work that challenges them without creating undue stress.

They didn’t sign up for riding the equity rollercoaster of ownership. That’s your job, as the business owner. You’ll (hopefully) get to experience the high of equity ownership, so you also have to feel the lows along the way.

Taken to the logical conclusion, that means you have to be a human anti-depressant for the business — your job is to mute the highest highs & lowest lows for your team, so their experience of work is more stable & calm.

(By the way, that often means that you, the business owner, need to take actual anti-depressants to help you manage the highs & lows for yourself.)

---

Conclusion

Pick your favorite analogy — punchable face or human anti-depressant — and sit with it. Are you excited to be that person, day-in & day-out, for 3-7 years at a minimum?

Is that the hard you want to be in? I know we valorize entrepreneurship in these SMB/ETA circles, but there’s no really no inherent superiority here…some people just are better-suited to getting punched in the face than others. They’re also worse employees in many cases.

One last thought. I’m a strong believer in growth mindsets, even when it comes to attributes. Given enough time, repetitions, focus, and discipline, I believe one can build up this attribute. It will be hard, and that’s okay.

As always, I’d love to hear if any of this resonated with you, or if you have thoughts to share — just hit reply to this email or find me on Twitter.

Best,
Kaustubh Deo // Guesswork Investing