“There are no rules. Don’t let anyone tell you any different.” 
Jim Everingham

Perhaps the biggest lesson I learned––though I struggle with it still––from my first startup experience was:

YOU ARE ALONE. You are Cortez at the shores of Veracruz.  There are no rules. There are no answers outside of those that you create for yourself. The King will not save you.

Accepting this fact was hard for me. I never fully embraced it until the end, when it was too late. The sooner you accept this truth, the better you will be.

What am I talking about? In my first startup, we had an all star cast of brand name advisors, lawyers and investors. I relied on them for answers to questions they did not and could not understand:

  • How do I get customers to buy our product?
  • How do I make something that people want?
  • Should we take new investment that’s painless to get even if the valuation sucks?
  • What should I do about my co-founder troubles?
  • How do I get acquirers interested in buying my broken, dying company?

These were hard questions with no obvious answers. Like many startup CEO’s, I was scared and unsure about what to do. The stakes were high, the money low and the path unclear.

In these moments, I would often pick up the phone and dial my CEO coach or corporate attorney (we were friends, she had lax billing standards). We would talk for 45 minutes or so and he/she would make a suggestion on how to handle the particular quandry. These calls left me feeling relieved, like I was back in control and doing the right thing.

This was a mistake.

In retrospect, I view this pattern as a bad habit, as an easy escape from the reality of the hard decisions I had to make as a CEO. No expert, no outsider could know what I knew. The only complete data set was in my head. I was truly free to decide and truly responsible for my decisions. The lack of structure, the uncertainty of it all was terrifying.

It’s one thing to climb up a big mountain and struggle on your way to the top. It’s another to not even be sure if you should be going up or down, or even if you’re really on a mountain at all instead of at the bottom of a pit. Oh, and your food supply is limited. When it runs out, you die. Also, your crew is on the cusp of mutiny.

In situations like this, it’s easy to seek an out. Mine was “expert” advice.

But the thing is: My most creative work, most insightful decisions were never the result of someone else’s advice. My best work happened when no one would pick up the phone, when I had no guidance, no options to choose from, no structure to follow. My best work happened when I was on the brink, when I was desperate enough to rely on my own wits, when I had no one to turn to but myself.

Example: In March 2011, SpeakerText was dead in the water. Our acquisition efforts to date had failed. Our largest investor had suggested we simply “die gracefully.” With the standard playbook of “warm intros” failing me, I threw out the standard playbook and started making up the rules. Instead of playing coy (as had been suggested by various industry veterans), I mass emailed every investor, advisor, CEO, and CEO list in my address book on behalf of an imaginary “friend”:

From: Matt Mireles
Date: Mon, Mar 26, 2012 at 5:16 PM
Subject: For Sale: Ruby on Rails Dev Team
To: XYZ@BlueShirtCapital.com
Hi [Investor/CEO X],

Need a badass Ruby on Rails team?

A friend of mine recently put his 6-person startup up for sale, and their engineering team is awesome. Two of the guys are Carnegie Mellon grads, another started programming professionally for IBM in high school.

So far, they’ve had a couple unexciting offers, and while the team is super-technical, he’s not particularly well-connected within the startup world. He asked me for some help meeting potential acquirers…

Interested in a lil’ M&A? Ping me and I can intro.


The response was overwhelming. I got four (!) dozen of leads from established companies and startups alike, three of which led to verbal offers and one of which led to an actual term sheet from a company you’ve heard of (more lessons here, to be blogged later). This for a broken, dysfunctional startup that, I was told, had no hope of being sold.

Lesson: Being an entrepreneur is lonely. Being alone is hard. There are no rules. Embrace this reality. Act accordingly. 

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