- Silicon Holler
- Posts
- When to make the leap of faith?
Few moments are put on a pedestal like the moment a founder quits their job to go full-time with their startup.
We have nicknames for it—”the leap of faith” or “all in.”
The popular narrative is that founders have to suffer when making this jump. It’s validated for many when you see Shark Tank star Kevin O’Leary saying he wants founders to eat Ramen noodles and scrape pennies, or when you see founders saying they actually did this for so long they became nutrient deficient (I can’t find it now—but I’ve seen founders brag on this, which is sad).
That wasn’t my experience.
Today I’m going to share how I made the leap, in hopes that it shows an early stage founder there are many ways to get started.
Side hustle days
The cofounders of GoWild were together and all in by the end of 2016. We spent January to September working on the product, and we launched our iPhone beta in September 2017. From late summer 2016 through the end of 2017, I was running a brutal schedule that often looked like this:
5 am - Wake up, work on GoWild
8 am - Leave for agency day job, maybe take a call on commute
12 pm - Lunch time calls for GoWild
1 pm - Back to agency gig
5 pm - Drive home, take calls with potential partners on west coast
6 pm - Wife leaves for night shift, begin dad time with my son
8 pm - Bedtime routine with son
8:30 pm - Begin work on GoWild
1 am - Sleep
Standing in my new office at the agency. I’d be gone within the year.
My wife worked three nights a week, so this wasn’t my schedule all week, but if she was working, this was the pace I kept. It was tiresome, but I was so excited about what we were doing that I looked forward to waking up at 5 to get to work. In hindsight, I’ve realized how important sleep is and would never recommend this for extended periods of time, let alone 18 months as I did.
I was standing in this exact spot when the idea for GoWild hit me. But dad wasn’t with me that day.
Post app launch, I was ready to dedicate more time to GoWild, but wasn’t sure when I’d make the jump. We had raised $445K at the end of 2017, but I didn’t quite feel ready to go full time. Replacing my current salary or even taking a bit of a pay cut would deplete cash faster than I wanted.
And then, a trip to the grocery store changed my life.
“When?”
In the first weeks of January of 2018, I turned 31, and was preparing for our first trade show. I was still full-time with the ad agency, but things were picking up with GoWild. I remember going to Costco around then to pickup a tablet to use for sales meetings at the trade show. I spent $350 or so for an iPad Mini and felt guilty for spending so much of our freshly raised cash.
Early GoWild promo mockup.
The week I was prepping for the show, I ran into an old client of mine in the grocery store, Russ Carroll, the founder of Ladder Now (now Seek Now). Ironically Russ fired our agency from his business, but he always liked me. He knew about GoWild, and as we were catching up amid the discounted Christmas items and fresh display of Valentine’s Day candy, Russ asked me a one word question.
“When?”
“When… what?” I said.
“When are you making the jump to GoWild?”
I told him I was trying to figure that out, and that I didn’t want to put my salary on the company quite yet. I could see he was thinking, but Russ is always thinking of something. We parted ways, he leaving with his bag of groceries, me heading to the produce.
First working prototype of GoWild’s Trails.
Within a few days, Russ reached out through GoWild’s customer service form. Soon we’re at a happy hour together. As he rips into a salted pretzel, Russ tells me what he’s thinking.
He wanted to start an internal marketing department. He’d give me a well paying contract gig for 20 hours per week, and I’d help him get his marketing efforts up and running, and I’d hire my full-time replacement. The gig would be six months, and would give me the ability to put more time into GoWild. I’d work out of their office.
A few days after the happy hour, I met with Russ again on a Friday afternoon, and within hours of that meeting, I signed the contract. I put in my notice at the agency on the following Monday.
GoWild launch party in Lexington, Ky., fall of 2017
The contract work was well paid, although didn’t match my current salary. I became a 1099 contractor for GoWild to make up the difference, and began splitting my time between Ladder Now and GoWild. I couldn’t believe the progress I was able to make on our company with that kind of focus. Within weeks, we were talking to Garmin, for example.
Over the next six months, we raised more cash for GoWild, and all three of my cofounders would go full time with the company before me. I left Ladder Now in October of 2018 after hiring my replacement, as well as a designer. Working with Russ was great, and my wife has kidded me several times that I should have just stuck with Russ (his company has been on a rocket since he founded it).
I’ll forever be grateful to Russ Carroll for what he did for me.
Lessons learned
There is a perception that as a founder, you’re going to find this perfect leap moment, where your startup magically starts making enough money for you to take a decent salary. It often doesn’t happen that way. Or at least it didn’t for me, and it hasn’t for many of the people I know who start companies.
Speaking about side hustling on a panel prior to leaving the agency.
Some founders never take a salary. Some take one from the near beginning with venture backed companies.
In my opinion, and based on my experience, your best bet is to find a solution that gets you the most time to work on your company, while keeping your salary burden off the company for as long as possible. This is a sliding scale, and unique to everyone.
The four founders at a party at my house, celebrating our first funding round. L to R: Donovan, Brad, Zack and Chris.
If early founders take nothing else from my message today, just know the moment may not be apparent on any kind of modeling. Situations change like the weather. I remember asking our first angel investor when he thought I should go full time.
He said, “I can’t tell you, but you’ll know.”
You’ll know.
Content idea for this week
For founders: If you’ve already made the jump, share your version of what that story looked like. How did making that leap make you feel? Any lessons you can share with your community?
For leaders: You may not have taken a leap to start a company, but you’ve likely taken career leaps that were bold, risky or scary. What was that like? Looking back, did you make the right move? Why or why not?
Who I’m listening to: Jason Isbell
What I’m reading: “With the Old Breed: At Peleliu and Okinawa” by E.B. Sledge
Follow me for mid-week updates:
Reply