Startup secrets: 7 lessons learned in 7 years

Ask any startup founders where they’ll be in seven years and the likely answer is: “Hopefully still alive.”

We all know that nine out of 10 startups fail, and most do so within the first five years. So, talking about year seven when you’re focused on immediate growth is a tough thing for new entrepreneurs to wrap their heads around. Trust us, we’ve been there.

Having hit our seven-year anniversary at EatStreet, we’ve learned a hell of a lot since we hunkered down in a dorm room to figure out how to order food easily online — and for free —– from every restaurant we love. And it got us thinking. We could probably help other first-time entrepreneurs dodge a few of the same hiccups by sharing some lessons we would’ve liked to have learned the easy way.

So, check out seven of the biggest lessons we learned in our first seven years.

1. Exploit experts — early and often

You need to find people who have been there, done that and absorb all their knowledge. Asking for help is intimidating, especially for younger entrepreneurs, but hearing real-life experiences goes a lot further than nearly anything you can find on a bookshelf.

Try your best to find a base of these experts locally. Here’s why it matters: You’re going to hit problems. An uncomfortable amount of problems. You need a sounding board and different perspectives. It’s amazing how people who have survived something have an entirely different outlook — and better solutions — than those who are in the middle of the chaos.

Ultimately, try to get some of these people on your board, more as operating investors. For example, one of our investors, James Crouthamel, has successfully funded and grown a variety of startups. He knows what he’s talking about and doesn’t mind getting down in the weeds with us. He brings more than investment — he brings knowledge. That’s critical for fast-growing startups that need credible guidance in a hurry.

2. Don’t ignore accelerators

It’s not easy to consider giving up equity in the company you’ve built from the ground up. But aligning with an accelerator was one of the best decisions we made early in EatStreet’s history.

When we met the team from gener8tor, we had already launched in three cities — Madison, Milwaukee, and Iowa City — and we were looking to replicate that model quickly on a national level.

We needed an action plan to make that happen. Accelerators, at least the good ones, have the networks and experience to expedite your strategy. We dodged so many missteps, saved time, and we can’t tell you how much money we avoided wasting. Know this: the amount of equity you give up to an accelerator is outpaced by the mistakes you dodge with their help.

There’s no way you’re going to be an expert in every aspect of your business. Example time. We didn’t know how to effectively recruit a strong sales team to serve markets nationally. Gener8tor did. And they helped us do it aggressively and quickly. The result was quicker, more efficient entries into new markets, which accelerated the growth we needed.

3. Culture evolves — go with it

One of the best things about starting a company is being your own boss. You set the attitude, and you set the stage for things like dress code, work ethic, company parties — you know, all the little things that make up that thing we all love to talk about: company culture.

But startups evolve and so do their cultures. Here’s what we’ve learned: Don’t try to prevent culture from evolving. Just be self-aware, so you can help it along in a way that keeps it true to your mission and vision, while ensuring the team is happy, too.

When EatStreet was 20 employees, the company was a heck of a lot different than when we got over 100 people. For starters, we were generally younger, fresh out of school, and with very little need for any type of corporate structure. We were too busy busting our asses to stay alive to think, at least consciously, about it too much. Culture just happened.

But as you grow, structure and scale are inevitable. It’s not a bad thing. Instead, adapt. The best way to do that is to listen to your employees. Then take action.

For instance, we used to throw big company parties, where we’d rent a bar and push the fun into the wee hours after excruciatingly long workweeks. Now, our staff prefers to go do a brewery tour or maybe mini-golfing. That’s a small example but it goes back to listening. Do that, and your culture will thrive.

4. Don’t stop hustling

You’re going to get tired but you have to keep hustling. We thought we were going to be at $100 million in revenue in five years, and EatStreet would be more like an interstate, filled with fast-flowing food feeding millions on a monthly basis.

Well, it’s a bit harder than that. Early on, each day can be a roller coaster. Things are going to change unexpectedly and faster than you think. Little things can become big things. Losing a key employee can slow you down. Or, perhaps a top restaurant moves on. It doesn’t matter. Push on, with a healthy mix of hustle and strategy.



5. Staying alive beats best practices

A million business articles will give any entrepreneur a million best practices for starting a business. Ignore those. OK, don’t ignore them, but know when to trust your gut in order to stay alive.

In the early days, when EatStreet was still, it would’ve seemed like a pretty great idea to get a designer to make the website look great and to improve usability. Given our focus on user-experience we wanted to incorporate this best practice. But then we wouldn’t have had the money to put toward acquiring diners with fliers and coupons, and we would’ve delayed our launch. A delay, or lack of those coupons, would’ve tanked us.

Similarly, it would’ve been a best practice in the early days to bring in specialized staff for things like human resources, marketing, etc. But with that comes costs. We erred on the side of overvaluing the risk of overspending because we wanted to maximize short-term survivability. This may go against some best practices, but it was the right move. If you aren’t around in six months, it doesn’t matter if you have all the right people for all the right jobs.

6. Pick one user story

Maybe this falls under the old adage of “you can’t be everything to everyone,” but for good reason.

For any product to acquire new users, it needs to wow them. In our case, it needed to convince them to use, and stick with, EatStreet versus the other options out there. So, you’d rather have 100 users with great experiences than 200 who had a lukewarm interaction with your product.

Remember, you have limited funding just like nearly every startup. We were in the same position. We could’ve picked a million different segments of diners to target — and today we do have more segments we target and have a core value proposition that’s appealing to them — but at the time we needed to be selective so we could focus.

It’s hard to cross the “wow” threshold, but the easiest way to do so is to tailor a product exactly to a customer’s needs (hence, why you want to pick one user story).

In the world of EatStreet, if a diner likes takeout, showing delivery restaurants is a distraction that only takes away from the “wow.” If they’re price-conscious, a $10-delivery charge is a no-go. If they don’t know what they’re hungry for, alphabetical ordering of restaurants is counter-productive. In the early days, that’s why we zeroed in on college students who already knew what they wanted to order. It let us focus, be efficient, and increase the odds of hitting the “wow” factor more frequently.

7. Don’t let data get in the way

Whaaaat? A tech company that isn’t putting on blinders to every input outside of hard data?

When we were looking for ways to grow EatStreet in the early days, we had truckloads of data, like “diners convert much worse on mobile than desktop.” Or, “diners spend the most time on the checkout page.” The data is invaluable and would have its time to shine. But we weren’t blind to other inputs, including our gut.

So, with the data in our back pocket, we instead prioritized an initiative to develop a technique to quickly build restaurant-branded websites, apps, and ordering widgets we could white label. This strategy led us to a core revenue stream rather than a one-time 2–3% boost we may have seen from more data-driven decisions.

Now, we’re not saying don’t listen to data. That’s ridiculous. Not every non-data decision is a good one and you have to use data to understand how users are interacting with your product. Instead, remember data is only one input to a solid product roadmap and growth strategy discussion. Leave room for calculated intuition.

Of course, we have amassed a lot of lessons in the first seven years, but these are some of the biggies. They’ve been critical to our growth, and hopefully can save other entrepreneurs from a few bumps and bruises in the early stages of startup.

Matt Howard, CEO, and Alex Wyler, CTO, co-founded EatStreet, a national online food ordering and delivery platform headquartered in Madison, Wis.

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