26 Hours

How I met with 26 startups for my birthday, and what we learned

For my birthday this year, I decided to give away 26, one-hour sessions to 26 different startups. A number of people have since asked about the project, so I put together a quick recap below. Thanks to all the startups who reached out and made this such a cool experience.

The Offer

The morning of my 26th birthday, I threw together a [simple site], and posted an offer to Hacker News. The terms were simple: send me an email, and we can spend an hour working on whatever you think would be most helpful to your startup.

I hadn’t thought much about the idea before that morning, and had no idea what to expect. I posted the offer around 3pm PST that day, and went out for a birthday dinner.

Over the next 48 hours, I had more than 120 startups reach out for one of the 26 spots. I spent the weekend replying to every email, and setting up time with 26 of the companies.

The Responses

The responses I received were all over the map. Everything from established startups I had used myself, to first-time entrepreneurs with little more than an idea.

Over the next three weeks, I held meetings over Google Hangouts with each company that scheduled a slot. I had offered to work on anything, but the discussions basically fell into 4 buckets:

The number of companies wanting to talk specifically about product launches surprised me a little. In retrospect, a company who is already preparing for / thinking about a launch might be a more likely to respond to an immediate offer for advice and validation.

I was also surprised at how few companies asked about fundraising. I was expecting there to be a little more “Hey, you were in YC, right? How do we get them to fund us? Can you intro us to investors?”.

Fortunately, I got very few of those questions. The folks wanting to talk about fundraising had legitimate draft decks, great questions, and were looking for feedback. I was really pleased with how those discussions went, and was happy to hear that 3 of those companies have raised money since.

4 of the companies had no demo or live product at the time we met.

4 of the companies had raised more than $1M in funding.

The other 18 companies had a live or demo-able product, with less than $1M in funding.

The Sessions

I really enjoyed meeting with the startups. I kept my own personal “score”, and felt helpful in 24 of the 26 meetings. Hopefully, the startups felt similarly.

A few common themes emerged during the discussions, and I’ve captured them here along with some of my thinking and advice.

1: The mythical “launch”

A large number of startups wanted to talk about launching their product. In general, I observed that many of these startups had created a mental barrier in defining the launch as some make-or-break moment for the company.

It’s easy to place an artificial importance on “launching” a product. As entrepreneurs, we tend to be over-achievers, and sharing an unfinished product with someone is hard. It’s hard because we’re consciously making the decision to open ourselves up to criticism.

At the same time, we know it’s impossible to launch a perfect product. There’s always an excuse to push a launch out two more days, a week, a month. But if we’re honest with ourselves, we’re often just delaying the potential discomfort of criticism.

At [Embark], we “launched” more times than I can count. Sometimes, that meant a Tech Crunch article and lots of new downloads. Other times, it meant releasing support for a new city on the App Store, and not having any meaningful change in users.

Some launches are better than others, and you get better at understanding which channels of communication work, which things you should measure, etc. But at the end of the day, a launch is whatever you make it.

As a young startup, there’s no reason you can’t launch one day, change the title of your Hacker News post, and re-launch the next day. Launching never has to stop — and it gives you the most valuable capital you can have: actual user feedback.

For the vast majority of startups, there is no “mythical launch” that makes or breaks the company. I like to think of launching as sharing my product with other people and asking for a reality check. If you can do that, it becomes less intimidating.

If you have something that can provide someone with net new value, ship it. See what happens. It’s almost always good for the product.

2: Pitch Decks

I saw a number of pitch decks during the sessions, and they all faced the same challenge that every other pitch deck faces: too much information.

When you first start working on a pitch, the natural tendency is to write down everything cool about your product. The problem is that most founders think that everything about their product is cool — which is great, but leads to really long decks.

I encourage startups to go through the process of writing that really long pitch deck first, with the understanding that it’s not the final output.

All the information you write down in that first pass is valuable thinking. It’s good to get on paper. But 95% of it exceeds what is necessary or consumable for your audience.

Look at the first pass of your deck, and put it through the “Demo Day” test. Assume your audience is sitting in a hot, crowded room after seeing 50 other pitches.

In three minutes, does your deck communicate what you’re building, why it’s going to be huge, and why your team is awesome?

If so, you’ve got a fantastic deck. If not, work on getting it there.

3: Outsourcing Technical Help

I had several groups of non-technical founders ask about outsourcing technical help. For some people, this might work.

In my experience, it hasn’t.

Outsourcing is tricky because you’re ultimately hiring a mercenary. The person might be really talented, but their perception of involvement is fundamentally different from yours.

They look at it as a job, and you look at it as your product.

Bringing in technical team members that are invested in the product is essential. Yes, it will cost equity. But it ensures a team that’s willing to do the extra things, and not just those they’re explicitly getting paid for.

People you know are always the best first candidates. People those folks recommend come next.

4: When to go full-time

Some founders I spoke with had gotten off the ground, but weren’t working on the startup full-time yet. This is a really tricky situation for some people, because it usually means making the call between a stable, known salary and the great unknown.

I battled with this decision myself, and empathize with the difficulty. It’s really hard to make decisions that challenge your quality of life.

Everyone’s answer to this question is different, but generally there’s a few things I’ve found helpful to think about:

1. If you’re already working on a startup on the side, there’s something you’re not getting from your current job.
2. If you’re already working on a startup on the side, you’re probably spending less time doing your current job well.
3. If you’re working on a startup on the side, you’re spending less time giving the startup a chance to succeed.

There are legitimate reasons for not being able to dive all-in. But most of the time, these are reasons we create for ourselves, and not actual barriers. There’s no one stopping us from resigning — it’s simply uncomfortable.

It can be a scary, scary thing to go full-time. And having some sort of investment is always helpful in making that easier.

But at the end of the day, a side-project startup will have a hard time becoming a full-time startup until you decide to treat it that way. And for most people, that means committing to it full-time.

5: Telling your story

This is the last piece of conversation that came up with nearly every early-stage startup I spoke with. In the first five minutes of our talk, I’d ask them what they were building. While everyone had an answer, very few companies were done answering in those first few minutes.

Being able to get down to an “elevator pitch” of your product is essential in telling your story. It’s the answer you give someone at a bar when they ask you what you work on. It’s the answer you give to the aunt you haven’t seen in 8 years. It’s the answer you give to an investor you meet on a plane.

In 30 seconds, tell me what you’re working on so that I “get” it.

Every piece of information that doesn’t help meet that goal should be saved for later. If you can’t make someone think “wow, tell me more” in those first few seconds, they won’t need to know the extra information anyway.

Getting to that solid, go-to pitch is deceptively difficult, and takes lots of practice. Try it out with anyone who will listen. You’ll get a feel for what sounds *right*, what sounds interesting, and what words you’re comfortable using.

When it comes time to tell your story, you’ll nail it.

Final Thoughts

The [26 Hours] project was awesome. I’m planning to do it again next year, plus-one. I want to say thanks to all the companies who reached out, and to the 26 companies I met with for helping me get better at helping other startups.

In the meantime, if you’d like to talk more about the project, send me an email, or reach out on [Twitter].