The Decision to Move On

Startups are hard. It’s not the long hours, the uncertain future, the fear of failure or anything like that – those are each challenging, but to me they aren’t why startups are so hard.

Startups are hard because they involve people. And not just any people, but people all working towards something they believe will happen, but not sure exactly how, when or if it will. It’s also the same people that you get to work with that is both inspiring, humbling and awesome, but also so hard.

It’s also the hardest reason to move on.

A few months back I began telling co-workers, friends and family I was moving on to my next journey after Zaarly. Sounds simple enough but when it is your company, it’s not quite that simple. Turns out it’s not just like moving on from any other job because in many ways you are always associated and connected with the company you start – once you are a founder, you are really always a founder. Funny enough, there aren’t “ex-” founders of companies (you found it or you don’t – you just don’t lose that title once you move on).

In the past four months since this transition began for me, I’ve talked to numerous founders who left their companies and learned that it’s never an easy thing to do it and always a delicate and unique situation. But most of the time the realities aren’t nearly as salacious as you might think, read or hear. Sometimes you just move on because that’s what needs to happen for the organization to succeed. No fight, no drama, no disaster… just life and startups.

Back and Forward

For me, the past two years of Zaarly were simply amazing – the most unusual founding story, launching at SXSW, rolling this unique concept out across the country, making a marketplace work and then recognizing you needed to make some bold strokes to get the company to fulfill the bold vision you’d set. And that’s what the unique group of founders and team members did together. I was proud of the people throughout, but perhaps the single most proud moment was how the entire team (all 45 of us) got through a product evolution that we believed was what our customers wanted. And to fast-forward nearly five months since the launch of Storefronts, I’m proud to see our passionate community of buyers and sellers we’re building. Much more ahead, but excited for that path.

And that’s the reason you can walk away with a big smile – proud of what you’ve accomplished together and proud of what that group you assembled continues to do as you move on.

As a founder my job will always be to trumpet the amazing work of those that continue on – I take zero credit for the hard work of those that are today helping our seller community to open their businesses and storefronts, and our buyer community to discover these amazing entrepreneurs. I’m just proud and want to use whatever opportunities I have to share my enthusiasm and pride in this company I helped start. As a founder on the outside looking in, you sometimes have to check yourself still – because while it’s still your baby, there are amazing people now helping that baby grow up. I swell with pride when my cofounders or friends at the company share their accomplishments and challenges. It’s great and always will be.

I’ve been incredibly blessed to be a part of a wonderful family and maintain amazing relationships with many members of the Zaarly family. As I’ve moved out of the daily grind in the office, I’ve had the privilege to volunteer with the great people at [Startup Weekend]( and help a wonderful friend and mentor [Steve Blank]( spread education designed to help entrepreneurs succeed in their businesses called [NEXT]( I’ve also discovered the people I plan to help with my next startup – business owners. While I am very early in that journey to build an awesome company, I’m excited to know who I want to serve with this next startup – and look forward to tackling the challenges and problems those business owners face in growing their businesses and helping create jobs in our economy.

Feels cool and exciting to be back in the throws again. Hard to get this startup thing out of your veins… and ready to start the journey again.

The Founder Playbook

Turns out there is no playbook for this founder journey and no one tells you potholes to avoid. If your company is acquired, the story is easier. If the company fails, well, that’s another story you can tell. But leaving when much of the story is left to be written, yea, that’s not so clear. I ultimately decided to write this post because I’ve met lots and lots of people who’ve been here and most say, “Just takes a bit.” That sure helps, but felt like saying to me “you’ll just know.”

As you move from a company where “it’s your entire world” to “it’s not your world anymore, but something that still defines you from the outsiders view”, it becomes a delicate dance. You want to continue to cheerlead and champion from afar once you’ve gone, but all the while you know you need to let those you’ve entrusted with your baby thrive. I’ve personally learned that moving on as a founder isn’t as natural as packing up your boxes, forwarding your email and changing your LinkedIn bio.

Plus, there is this unique perception about the founder relationship that seems to be more than just “an employee leaves.” Instead when it is your baby, your company and you have such a deep association, people’s mind’s always jump to questions like “Why?”, “Is the company alright?”, “Did you get in a huge fight with your cofounders?”, “Is there more to the story?” or “What does this mean for you?”

People want a simple answer as to “why” when it’s nearly impossible to simplify. For me, sometimes you just move on because that’s what the organization needed to thrive. No punches thrown, no screaming, no board room debates, no looming disasters… just life changes and startups do to. Yup, startups are still just about people and it’s okay that they move on. Then your goal is to ‘do no harm’ and help give the organization the best chance of success.

It took me about two months to get my hands out of the company and untangle from the webs all founders weaves. From there it took me about two more months to be ready to start dating another “pretty startup idea.” But it does take time. And so here I am today – a little over four months since beginning this journey to “move on.” Now I can smile in the rear view mirror and be jacked about the road in front of me – all while now full of some incredible new learnings and knowledge about life, culture, people, companies and myself.

What’s Ahead

It’s a great time in my life and I’m thankful to be able to support, work on and grow some great organizations and people in each of these endeavors - past, present and future. I’d say I’m most fortunate to have a wife Allison who supports me as a “serial entrepreneur” (even though she sometimes wonders why I can’t just get a real job), and a group of friends, mentors, cofounders, investors and colleagues that cheer for me no matter what.

Turns out startups are just plain hard – because it’s one of the most intense, people-driven experiences you can have. And each person adds exponentially more complexity, challenge and uncertainty. But those same people also add to the amazing factor, in that they support you, challenge you and force you to be great.

You often wonder during those months of transition, “What do people think of me – am I a quitter, did I leave them too soon, am I a failure or is it something else altogether?” Turns out you are just you – an entrepreneur. And the response from those that matter is nearly always, “I’m excited for you to tackle whatever is next.” That’s great to have people like that in your corner.

I’m excited about the next journey ahead – if I meet 1/10th of the amazing people I’ve engaged with during the last two years of Zaarly, I’m in line for a pretty cool experience. Love meeting people, stimulating my brain and finding something inspiring to try and solve.

Startups are hard. Moving on is hard. In both cases, it’s the people that make them so. Maybe that means you are doing something right if you’re surrounded by people who make your life so amazing, it’s hard.


Now read this

The Embarrassment Test

“Use your gut to make big decisions; use data to drive tactical changes” - Rich Barton In startups, it is easy to find a dissenting opinion. Turns out if you are doing anything that is half-way interesting in your company, there will be... Continue →