Don't Emotionally Bootstrap Your Startup

“Sure, my co-founder and I have mild PTSD...but we’re just knuckling through”

“You’re just knuckling through?” I replied.

“Yes”

(I paused)

“If I was a friend of yours and I told you that I had PTSD and that I was just knuckling through it, what would you say to me?


A few weeks ago I sat down for a catchup call with an old friend that turned into a mini-coaching session with that simple act of reflection - repeating back what I had heard. It slowed the conversation down enough so that we could both hear what was happening. (this is one of the reasons that cadence is an essential element of my Conversation OS Canvas)

I could have just laughed along with the inside joke. Hah Hah, isn’t repressing trauma funny?!

But my interest is always in taking a conversation deeper, to the heart of the matter.

I asked her if I could offer an alternative perspective.

Now, some folks will tell you that coaching is *never* ever about offering advice. But I knew how to pivot her understanding of an essential startup philosophy and learn to apply it to herself. 

Also, I’m her friend, and you can’t coach friends, right? 

In my defense, I asked for permission first. Key point. Advice without permission is...well, it sucks. (Invitation and Power are also key elements of the OS Canvas, just saying)

See, this friend of mine has been starting up a company for the last few years. It’s taken off...they’ve been selling well, and getting some great placements, requiring bigger orders...which are complicated. Pricing a product depends on how much you are planning to make over time, the amounts you make may determine the manufacturing process. (This is, by the way, a physical product. They are, for lack of a better word, hard. (It’s a pun.))

The uncertainty in demand was making it hard to price the product competitively. The difficulties in pricing were making it hard to negotiate with bigger buyers quickly. No one likes the phrase “negotiations were dragging on” ...but they were.

On the call, she’d admitted to me that if today, she was handed her company, with all of its challenges, she’d be thrilled. She’d get right into problem-solving mode and knock ‘em down, one at a time, like the boss that she is.

But most of these problems are ones that she’d created, herself. As she’d been explaining to me during our conversation, she had bootstrapped her company, launched the product as an MVP, and had been scrambling ever since to scale it properly, mostly by rebuilding it from the ground up. She had already shared with me how bootstrapping had created all of these challenges for her, and how she was being more intentional about building her product’s solid foundation. 

So I knew that the word “bootstrapped” meant something to her. She had been living it. And she knew all about how, eventually, you have to start over...sometimes from the ground up and (re)build a solid foundation. 

She just wasn’t using that language on herself. Nor had she realized that the emotional state of her company and her own emotional state were so intimately intertwined. 

I am a total bootstrapper, so I empathized. Maybe you are, too? I love to just get an idea out there and see what traction we can get. But that is outer bootstrapping. 

What she was doing was inner bootstrapping.

A few years back, I wrote on a sticky note:

“Don’t emotionally Bootstrap your Startup”.

emotionally bootstrap-white-balance.jpg


Since I wrote that sticky note I’ve done a lot to reduce my own inner-bootstrapping. I have a coach, I work with an executive coaching mastermind as I deepen my own executive coaching practice, I have a men’s group that meets weekly (it’s like crossfit for my emotions), a therapist and a slack channel filled with innovation consultants who are all more talented than me, and generous with their insights. And...yet...It can still feel lonely and hard sometimes. 

Some people will tell you that a coach can’t tell a personal story, or offer advice. In this case, I knew that sharing my sticky note and its back story with her would help her rethink her inner-bootstrapping mentality.

When I shared this idea with her, I watched her shoulders lower an inch. She took a deep breath. She started to step back from being inside of her pattern to watching it from the outside. She felt seen.

She could begin to ideate about what *she* could do, and wanted to do, to help herself put on her own oxygen mask. 

But this was just the start. Trauma takes time. So we got to a deeper question: How could she forgive herself for creating her problems? 

Self Empathy, or empathy for a past version of yourself, is a powerful tool. Having a conversation with your past self is possible. Having a conversation with your future self is possible too. 

In fact, that’s where we finally got to. What did her future self want from her? What path would get her towards meeting that version of herself?

These are conversations worth leading with yourself and for others.