Cheaper Than A CoFounder

Every founder knows that while this is the greatest ride of their professional life, it can be a lonely one.

When every decision ultimately comes down to you it’s the compounding effect of a thousand little cuts that gets to you.

Even when business is going well it can feel isolating.

You can’t go “downstream” and spill your guts to your team members (even the most senior of them).

There’s nowhere “upstream” to go, cause you’re the boss. The proverbial buck stops with you.

If you’re the type to have a cofounder then sometimes you can chat with them about what you’re struggling with. In my career I’ve had cofounders in previous ventures, but today I’m a single, non-technical founder at Castos, and I really like it.

But the reality is that even if you do have a cofounder, there are just some things that you can’t talk to them about.

Is it time to sell?

Having issues with your cofounder?

Don’t have the passion or conviction for the business that you once did/

Wondering what you’re doing all this for…?

A Better Solution

For most of my time at Castos I’ve had a business coach. These individuals have been key in me keeping my sanity, making good decisions, and navigating this endlessly complex world of building a startup.

Quick shoutout to the coaches who’ve helped me get here:

• Adii Peinar
• Rob Walling
• Mike Del Ponte

There were always a handful of strict criteria for the type of person I’d want to work with as a founder coach:

• They’d done this before: This person had to have been a founder, and ideally exited their company or put it on autopilot and exited the day-to-day.
• They know SaaS: doesn’t have to be that they ran a SaaS business (only 1 of mine had) but they have to know the online business space.
• They had to have been “in the game” recently: one issue I see in the coaching space is when people coach but haven’t run a business in the last decade.
• They had to offer 1-on-1 coaching: I’ve done the group coaching thing, and it’s not for me. Mostly because the leader of the group can’t give me the specific direction I’m looking for.
• They had to help with growth: This is the key to everything. A coach who is growth-minded and really practical. Not too much “woo-woo” dreamscaping, but really practical next steps to move the business forward.
• They help small businesses: Lots of coaches out there for true VC-track businesses, but I’m not one of those. So need someone in the $1-5M ARR range.

Pretty tough list to find someone who’s done all of these things, and recently. But I did, several times, and it was a really great experience.

Against The Solopreneur Track

I see so much about being a “solopreneur” in the Twittersphere these days, and honestly I can’t imagine anything more exhausting.

Being the only one responsible for absolutely everything in your business is a fantastic recipe for burnout.

I’m much more the type who loves being the glue that holds things together. I’m probably a mix of an Integrator and Visionary, but at this point in my career certainly am not often the one who’s in the weeds implementing the details of most projects.

As a result, my highest leverage time in the business are our weekly meetings either as an entire company or within a functional group, where we review the previous week and solve any issues that have arisen (pretty standard EOS stuff).

Who Needs A Coach?

Yes, this is a sideways pitch for the value of a founder coach. Mine have been invaluable to me keeping my sanity, making (mostly) the right decisions in the business, and helping me level up as a founder.

But who is having a founder coach right for?

I’d say if you:

• Are a solo founder it’s a no brainer. You can’t expect yourself to make good decisions all the time. Having someone to bounce ideas off of is massive.
• Making a big shift in the business. This could be things like raising capital, considering an exit, or just starting out and needing to nail a GTM Strategy
• Are feeling isolated. Not using the word ‘lonely’ here cause it has negative connotations. But if you just don’t want to do this alone anymore.
• Need specific help in a functional area. This could be growth, team, mindset, BizDev, you name it. Having a specialized coach in an area could be great.

I titled this post “Cheaper than a cofounder” because I think that’s how many of us approach the process of filling the gaps in our own skillset or emotional capacity. But it doesn’t have to be that way.

Having an experienced, third party, objective coach on your side (ideally one who has been there, and done that) is in some ways a lot more valuable than someone else who’s in the shit, figuring this all out realtime.

I’ve recently started offering founder-led growth coaching to a handful of founders, and it’s been immensely valuable for me, and for them. We have twice monthly, 60 minute intensive sessions. In each session we identify what’s holding the business back at that moment, formulate a plan for how to attack it, and then leave with concrete next steps for the founder to move the business forward.

I’m enjoying the hell out of these sessions. They challenge me intellectually, but moreso it’s a great way to give back to the community of SaaS founders who have come before me that have helped me so much.

Whether you get a business coach or continue to go it alone, I hope this is helpful in shaping how I think about the value of a business coach, and where/why it might be a good fit for you.