The Boring Stuff Will Break You
How entrepreneurship feels more like quiet pain than flashy wins.
The ability to endure pain, or sustain mundanity for a long period of time is what truly defines entrepreneurs.
I’ve been thinking about this concept a lot lately.
Maybe because I’ve been listening to Cam Hane’s new book… idk.
I’ve spent my entire career in high growth, venture backed startups during the best decade of tech…
I’m pretty sure the ‘slowest’ year I had was only hiring ~15 reps in a single year.
This was in addition to raising venture capital every 2 years and what felt like everyone and their mom wanting to be part of your cool high growth startup.
To now…
Running 3 small businesses from a basement office with a small window.
No team besides my wife and two very part time contractors to work through challenges with and get everything done that needs to get done.
Nobody cheering you on when you get a deal.
No CEO to tell you if you’re doing the right things (or wrong and what you should actually be doing)
Nobody cares or even notices that you’ve sold everything you own to provide enough cash runway to pay bills, buy parts and grow your businesses including your truck, camping trailer and what would have been a beautiful piece of property to retire on someday outside of Park City.
It sucks to have to swallow your pride and really dig in.
But I’m grateful for the chance to swing for the fences.
I’m grateful for the lessons we’re learning & the grittiness of trying to figure out new ways to do things or optimize small functions of each business.
My therapist helped me gain some new perspective:
"Blake, what if instead of focusing on the cash today, you took the approach of simply building these businesses with your wife as a learning journey together.
What if you removed the pressure of it all and just focused on each step being a learning opportunity that you and your wife get to experience together, in a setting that you’ve never experienced together? In a way, you’re learning a side of each other you’ve never experienced in 14 years of marriage…”
This hit me hard.
First of all, I recognize what a privilege this is. To own 3 small businesses and not have to ‘worry’ about cashflow from 2/3 of them…
But I feel extremely grateful for the chance to be able to to burn down cashflow as we’re growing, learning & scaling.
As PJ wrote:
“Success isn’t about being a genius on your first shot. Just ask the data (which tells a sobering story).
1st time startup founders success rate: 18%
Those same founders success rate by 10th attempt: 65%
"Better than yesterday" isn't just motivational fluff. The idea of becoming an overnight success is a fantasy. A harmful one. (and this doesn’t just relate to entrepreneurship) It's how mastery actually works.”
So, here’s to leaning into the journey and trying to make it a bit more fun.
A bit less on the outcomes.
A few big accomplishments from last week:
Appleton
We landed our single biggest purchase order this week since buying this business. >$70,000. Big win.
Consulting
I’m been working with only 2 clients to help build a GTM motion. Both happen to be selling into healthcare, dramatically different businesses. I’m building a sales team from the ground up and we’ve recruited, hired, onboarding and are ramping our first rep with wild success. Big win.
Vending
Big momentum here. We’re crossing our 2 year mark in a few weeks and we’re making a lot of adjustments and changes. This will be a big focus for us in the coming years.
We met with a current clients this week whom we have a 5 year contract with. It’s a location that sees over 1,000,000 visitors every year and we have 4 (going to be adding more + bringing in AI Fridges) machines in this location. One of our better locations for sure. Big Win. Stay posted for a 2 year recap & the next 3 year plan.
What’s Coming?
→ Podcast episodes - My wife and I are going to start ‘documenting’ it all. Part of this is recording our recaps of our ‘exec meetings’ and sharing those learnings in bite sized chunks. Check it out here.
→ Check out my more popular episode, 05 | He bought a micro-saas for $140k and scale >$1M in Value | Eyal Toledano
→ More video content - I’m exploring ways to do more around showing what it’s like and day to day of running a small business. Follow me on LinkedIn for more.
Great post Blake. I felt this
“No team besides my wife and two very part time contractors to work through challenges with and get everything done that needs to get done.
Nobody cheering you on when you get a deal.
No CEO to tell you if you’re doing the right things (or wrong and what you should actually be doing).”
I left a big company with the resources/systems in my late 20s. I thought I was going to crush it in my own, but I was in for a rude awakening when I realized I wasn’t a top performer without all of that support.
But working through it led to growth and confidence. Well…it led to financial stress for my family and my first therapist :), but now that I’m on the other side I can appreciate the hardship and hard work to get through it.
Congrats on your big win last month!