Jon Crawford is a product and engineering-focused entrepreneur who made a life-changing migration to San Francisco six years ago. After spending two years in Kansas City building a social ecommerce platform called Storenvy, Crawford found himself adrift in San Francisco when his startup earned and lost a space in Y-Combinator’s Summer 2010 class in a heartbeat. He chose to stay in the city, and after a half-decade solo hustle, he’s raised $6.5M and made Storenvy host to more than 50K online stores for unique and emerging brands. Crawford joins FounderDating this week to talk about the psyche of an entrepreneur and what it’s like being a solo founder.
Where did the idea for Storenvy come from?
I had taught myself to code and was running a web design shop in Kansas City right out of college. I found myself building loads of online stores for small businesses; in ‘08/’09, there weren’t good solutions for people to create their own online storefronts. I thought, “what if we took the idea of free and social and applied it to commerce?” that democratizes commerce the way email has been democratized—everybody can have an online store, and we give it away for free. Then, we’ll tie them all together to create a sort of online mall, and that networking will make it more valuable than just having your own store.
Storenvy has an innate social aspect. Store “owners” get passers by seeing stuff, they get updates when you release new stuff or you can “envy” things. There’s also a feed where you can see the stuff everyone you’re connected with thinks is cool or updates on their activity. It works similarly to sites like Pinterest or even Reddit, where the popular items bubble up to the top, and it changes every day.
Does that feeling of intense crunch time ever stop for a founder, or do you feel like you’re still on the same roller coaster you were at the beginning?
You can never solve all the problems. At any given time you have some ten problems that are worth your attention but only enough time to work on one of them. And when you get done with that one, you still have nine left and another has popped into the queue.
If you like solving problems, it’s great. If you like having a healthy work-life balance, you might want to look for something else. Tweet this!
There were (and are) times when I felt like I had to hustle hard to make something happen. And then there were actually even more times I had to work just to keep up with things that were happening. Sometimes I had to will things into existence, and the other times I had try to keep up. They seem to just keep trading off; it’s always one or the other. Most of the time you’re either working really hard to make something happen or working really hard to keep up with what’s going on.
Fundraising, for instance is always a “work-your-ass-off to make it actually happen” phase. I was very fortunate the first time because I had delayed—I had been working on Storenvy for almost two years when I decided to raise money, and I had a load of traction and a really built out product. I didn’t even have a team. It was just me, and we raised $1.5M in a seed round without any employees, and it was simply because I’d built a product that a lot of people were already using.
Then everything else after that has been impossibly challenging. We had a very hard time raising our Series A, like most people do, because we hadn’t launched part of our product that I had wanted to—we just didn’t get it done fast enough. That was four months of grueling hell. At one point we were a day away from a zero balance in our bank account, with payroll coming right up. That’s when I finally got the “yes” on the Series A.
Three months ago you wrote a blog post about 9 days into doing a cleanse and taking a break from the “rock ‘n roll startup lifestyle,” where you talked about feeling mentally more alert but also less social and maybe even a little less motivated. How did that turn out?
Right now I’m kind of peeling back my Storenvy responsibilities to come up for air and “Eat, Pray, Love” a little bit. At the end of the day, you might want to make a big impact and express your big fancy idea, but your work will never hug you back.
Your work will never be there for you when the going gets tough. I’ve spent the last year learning how to actually enjoy the present moment and create a life that I enjoy. Tweet this!
I love it. I know I will come back to it.
Is it possible to found and build a successful startup without running yourself down? 
No. Randi Zuckerberg captured this in a tweet years ago. She said: work, sleep, family, fitness, or friends—pick three. It’s true. In
order to kick ass and do big things, I think you have to be imbalanced. I’m sure there are exceptions, but every person I’ve seen riding on a rocketship was imbalanced while that rocketship was being built. You have to decide if you want it. If you want to spend a lot of time with your friends and see all the Oscar-nominated movies and get good sleep at night and exercise, then it’s going to be hard to give a startup everything it needs. If you care about your startup more than you care about all those things, then go for it. But it comes with sacrifice.
What are your top three pieces of advice you wish you knew when you started or that you want to give entrepreneurs now?
1. Find cofounders. I don’t have them. So I’ve been playing the role of three people for years. There’s no one there to take over when I get tired, no one to check my work on board decks, and no one to cover that interview or meeting that I can’t quite make, so I have to make it. There’s also no one to talk through crisis moments with.
Anyone thinking about founding their first company solo should really think again. I’m sure there are many, many exceptions to this. But my experience has been that it’s going to be extremely, unnecessarily painful to do it alone. Tweet this!
2. Learn to communicate process to your team. I wish I’d known how to communicate my process to my employees better. I couldn’t articulate it. Because I was the guy who dreamed, designed, coded, and pitched it to investors, much of that process wasn’t even in words; it was feelings and instincts. I didn’t know how to turn it into English. When you get employees in the room, you have to teach them how to be part of it. “How to Storenvy,” essentially. I tried to teach people and I wasn’t good at it for a very long time.
3. Talk about vision way too much. Evan Williams from Twitter said if he could go back he would talk about the vision more because he and his leadership team are thinking about it all the time but the guy writing script isn’t. Remind people on a daily basis why they’re showing up for work.
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