Ryan Mickle

@ryanm

Starting a startup is fucking hard

Avoiding avoidable mistakes, the story of a new product I made to find the best startup tools, as recommended by YC, VC-backed, and leading bootstrapped startup founders

Update: We launched Founderkit! Be sure to check it out and let me know what you think.

In fact, starting a startup is the hardest thing I have EVER done in my life.

I remember getting into Y Combinator like it was yesterday. At that time, YC was quickly gaining steam as the “Harvard of startups,” led by its intense, charismatic founder Paul Graham. My co-founder Ed and I had prepared for the interview with a 24 hour non-stop grilling session, where we rapid-fired questions at each other, and were interrogated via Skype by YC alumni friends like Rod Ebrahimi, Nacho Thayer (the Readyforzeros), and Joseph Walla (Hellosign).

The interview, with all eleven YC partners in Dolby surround, as I described to Ed afterwards, felt like we were run over by a 100 car train, hitting every axle straight in the head as it steamed over us. We couldn’t stop replaying the interview blood bath in our heads, so we distracted ourselves until we got the news later that night with as much beer as we could drink, without embarrassing ourselves too much if the impossible happened and Paul Graham called us that night. When he did, all I could say was “PG? You want to fund us? Really?”

Ed and I were given an incredible gift that day, receiving access to a network of entrepreneurs who would be there to support us, no matter how hard things got or what question we faced. We were never alone.

The mistakes you will make in your first, second, or tenth startup will make you laugh, and want to cry. You’ll waste months, maybe years, and possibly more money than you may ever see again in your lifetime. If you don’t accept it now, you’ll accept it later, trust me.

When Ian Hunter and I decided to work together, we wanted to give binoculars to founders, to see the horizon and avoid mistakes, or at the very least, give us all a fighting chance to make smart decisions.

Building FOBO using Parse was probably the most regretted decision we made in our startup. What pained us the most was that it was run by friends, who built the service in our batch. Using our bank caused us some pain, but only in monthly doses. We fired our first bookkeeper because they made bookkeeping as enjoyable as swallowing a box of nails, but not soon enough. While at Zaarly, going with PoundPay was a giant mistake, Ian admits now. They should have used another payment processor, but they let themselves get talked into it. Each of these decisions were aided with recommendations, by friends, VCs, smart people, but they were loaded with bias, and likely just came from the wrong people.

Generally, we founders ask for recommendations when we make decisions. And who you ask makes a huge difference. People generally have no problem recommending a solution, even when they aren’t actually well-versed in something as specialized as starting a startup.

So in YC, we’d ask each other via the email list. But even then, the same questions would continually be re-asked, like a broken record, such as which business bank to use, accountant, newsletter email service, payroll service, server, etc. I mentioned this to Ian, and we both grew excited to build something smarter. Ask the right people the minimum amount of information (because the best people to ask were the busiest), and get data that founders could actually trust.

One of hundreds of questions asked by YC founders for advice on tools to use

The first version of Founderkit actually started as a spreadsheet. In a matter of hours, it was obvious that we needed to build a scalable way to share the data with other founders, even with only that of 10 contributors.

Then came Founderkit. First, we invited YC founders to try it. Since we’d started with a spreadsheet and already had some tool recommendations, founders who joined were immediately surprised that is was actually useful. Chicken and egg problem? Simply an excuse used to justify inaction by people who don’t actually want to build something. Not so for guys who’d built multiple marketplaces. It wasn’t long before YC was sending all its new founders, with each new batch, and we had basically every active founder relying on Founderkit’s recommendations.

You may be thinking “aren’t there sites that do this?” And of course there are. Yet every time we’d show founders what we’d built, and the recommendations, they’d find some new service and implement it, based on the candid, quality recommendations we’d surfaced. We’d save them hours or thousands of dollars, in a glance. No other service in existence could do that.

Wait! Is this a story about Founderkit, or about how fucking hard it is to start a startup? Both.

Before launching, Founderkit had grown to almost 1,000 YC founder contributors. In past weeks, we’ve added Slow Ventures, First Round, Social Capital, Upside Partnership, Fuel Capital to Founderkit, and have others waiting to join. It’s been humbling to receive the support and contributions of such an experienced community of founders, and we’re grateful to have the opportunity to now share it with thousands of new ones.

Best of luck in your journey. We don’t choose this journey because it’s easy, we choose it because it’s the only one that makes sense.

And finally, come join the community at Founderkit. We’ll make decisions together easier, and save each other time and money on the avoidable mistakes, because let’s face it, we don’t need to make starting a startup any harder on ourselves.

Thanks for reading, and the great feedback, Ian and Shane!

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