Five things that are non-obvious as a first-time startup founder

Kwindla Hultman Kramer
The Startup
Published in
6 min readJan 1, 2018


Hi, I’m Kwin, co-founder of and two previous startups. This post is part of a series about startups, tech, and startup founder skills. I’m always happy to be helpful to startup founders and people trying to break into tech, if I can be. Feel free to schedule a video call with me, here.

Every startup company (and every startup founder) is unique and each startup journey follows its own path. It turns out, though, that many of the basic challenges we face, as founders, are pretty similar.

Over the past couple of years I have started to notice that every first-time founder I’m close to learns the same small handful of lessons early on. Thinking back, I realized that I climbed up that exact same learning curve, too. (And sometimes I learned way too slowly!)

Here are five “counterintuitive founder lessons” that seem to come up for everyone, regardless of company focus, type of product, or business model.

1. Nobody makes real progress on a startup until the startup is a full-time job.

It’s pretty common for me to get a phone call from a friend-of-a-friend, a founder with a “new” startup, and to hear that the founder has a full-time job at a big company, and that the startup isn’t really making any progress. Often, the startup actually isn’t all that new; the founder has been working on it, nights and weekends, for a year or more.

I always give the same advice: if you really want to do a startup, you’re going to need to quit your “day job” sooner rather than later.

This is scary, and hard advice to follow. It’s not necessarily easy to say why it’s true that you can’t make progress part-time. Empirically, though, the evidence is clear: I’ve never seen anyone I know make significant progress on their startup while they also still have a “real” job.

2. Don’t worry (early on) about competition.

Founding a company is pretty much the same thing as being obsessed with a product and a market. It’s natural to know a lot, and to obsess about, what other people are doing that’s similar. First-time founders usually worry a lot about competition. They don’t want to talk to other people about what their startup is doing, because they think competitive companies might learn something useful. They spend a lot of time thinking about complicated partnerships or specific product development plans that are motivated by a desire to outmaneuver competitors.

It turns out that it’s almost always a huge mistake to spend precious time and brain cycles thinking about how to “beat the competition.”

Startups fail for lots of small reasons, but mostly for two big reasons: they don’t make something that people are willing to pay for, or they don’t have a cost-effective way to tell people they exist.

So spend all your time thinking about those two things: product, and customer acquisition.

3. Tech startup success depends surprisingly little on technology.

I’m a founder with an engineering background, and I was slow to learn this lesson. For a long time I thought of a “technology startup” as a company that was particularly good at and focused on engineering. But it turns out that engineering is the fourth or fifth most important competency of a tech startup.

Startups first have to make something people are willing to pay money or attention for. Then they have to let people know about the thing they make. Then they have to get very good at “scaling” — growing and accelerating everything the company does. Technology helps with all of these activities. But, by the same token, all of them are fundamentally about something other than engineering itself.

If you love writing code or designing circuit boards, it’s worth knowing that starting a company is a very bad way to keep doing those things. Founders usually have to step out of engineering roles as soon as a company gets a little bit of traction so they can focus on helping the company sell stuff, and then scale.

4. Fire faster.

This is the hardest of these lessons to learn, for almost everyone. But it’s really important. Not everyone you hire will work out. And if you take too long to fire people who aren’t doing their jobs (and everyone takes too long to fire people, when climbing up the founder learning curve), you do real damage to your team and your company.

Firing people goes against almost all the (very good) instincts and values that founders have. Founders are optimists. Founders think problems are solvable. Founders believe that working hard and caring about what you do means that anyone can do pretty much anything. Founders tend to take responsibility for fixing things.

But it turns out that unproductive employees are amazingly, unbelievably toxic to the culture and happiness of a small team. As a founder, the most important resource you have is cash to make payroll. But the second most important resource is the happiness and alignment of the people who come to work with you every day.

You owe your team the best possible work environment you can figure out how to provide. That means you either have to fire people, when they aren’t working out, or you have to fire yourself so that someone else can make those decisions for your company.

5. At the beginning, almost all that matters is shipping quickly, then iterating.

Most founders, early on, take way, way too long to ship their product — to put what they are building in front of actual (and ideally, paying) users. When you’re obsessed with your product and have poured hours and hours into it, it’s hard to let go. You want it to be perfect. You know how much better it will be with just a little more work.

But this is exactly backwards. Products get better when people use them and tell you what you got right and got wrong. Nobody builds successful products in a vacuum.

This is such an important lesson that there are a lot of great founder quotes about it. Reid Hoffman: “If you are not embarrassed by the first version of your product, you’ve launched too late.” Steve Jobs, even more succinctly: “Real artists ship.”

I’ve been part of the founding team at three companies and two non-profits. It’s addictive, and fun, and fulfilling. It’s also draining, and difficult, and frustrating. Having investors and board members who are experienced, accessible, and kind helps enormously. So does spending time with other founders and building relationships that allow you to talk honestly about what’s hard, and what you’ve learned. Being part of a startup accelerator is great, because it gives you a network of both mentors and peers.

My current company,, makes video conferencing hardware and software for startups, and other small companies that do creative, fast-paced work. Check out what we’re doing and tell us what you think. — easy, powerful, video calls on your own custom domain!

And let me know what you think about this post in the comments below. Or, I’m @kwindla on twitter and instagram, and, the old-fashioned way.

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Kwindla Hultman Kramer
The Startup (formerly Pluot), Oblong, Media Matters for America, AllAfrica -