This last year feels like a whirlwind. I learned so much and it went so fast.

I spent much of 2016 – 2017 immersed in MBA classwork at the University of Iowa, but when I wasn’t doing that, I was often exploring my passion for startups.

Entrepreneurship events frequently popped up in Iowa City and I was quick to attend. And so, I found myself at Startup Weekend 2016 in Iowa City in the late Fall.

Here’s how I evaluated the decision to attend:

  • The theme was fashion tech. I like fashion, check.
  • Make a startup in a weekend. Obviously, check.
  • Spend the weekend getting out of your comfort zone through doing pitches and customer discovery, check.

So on a Friday afternoon there I was in a room full of strangers who would soon become teammates, friends, and fellow entrepreneurs. I was pumped, and a little nervous.

The event kicked off with around 25 people pitching their personal business ideas. Then through voting the ideas quickly narrowed down to 6, and then through the process of team forming narrowed again to only 3 ideas, with 3 teams forming around them.

From there the weekend progressed into making a Business Model Canvas, doing customer discovery, evaluating the customer discovery, pivoting the idea, more customer discovery, creation of an MVP and a 5 minute presentation slide deck.

If you’ve never done customer discovery here’s a quick video explaining the process at a high level.

It was an intense and fast paced weekend to say the least. At the end of the weekend  I presented my team’s business pitch in front of a panel of 3 judges, all entrepreneurs themselves and all around great humans.

Here’s a quick shout out to them and what they do:

  • Dave Tominsky, Managing Director at Iowa Startup Accelerator. Dave helps entrepreneurs succeed and is growing the Iowa startup community in big ways.
  • Emily Carlson, Founder of Written Apparel, a company making designer statement pencil skirts.
  • Steve Shriver, Founder at Eco Lips, an organic and fair trade lip balm company.

The result of the competition: my team won first place! It was a fast paced, exciting, fun, humbling, and very educational weekend.

After the weekend, some companies continue with their ideas while others drop the business but take with them the lessons and skills they developed in that short 3 day span. My team did end up disbanding after the weekend, but I decided to continue to work on the idea because it’s something I truly believe in.

Regardless of where I take this startup, I learned many valuable lessons that weekend about getting out of my own head, making a lean startup, and pushing myself out of my comfort zone. Whether this startup succeeds or a different startup I work on succeeds in the future, the most valuable part of the weekend will always be what I learned, and that’s what I’ll bring into the startup I do make.

The most important lessons I learned from Startup Weekend are:

  • Don’t get too attached to ideas.
  • Run your startup lean, especially in the beginning.
  • Face your fears and push yourself out of your comfort zone.

I’ll dive into each of these in more detail.

1. Don’t get too attached to ideas

The event started with 25 ideas. This narrowed down to 6, which further narrowed to just 3 during teaming.

How many of those ideas do you think made it through the weekend?


None of the original ideas stayed as they were when the weekend began. When you think of a business idea it’s usually just a hypothesis. You think people will really love this service you imagined or you think you can help people in some specific way. You think it’s great and of course you do, it’s your idea.

Now you could do next what many aspiring entrepreneurs do, and spend a year building that hypothesis into a real business in isolation. Sometimes you rely on the support of your friends who love you, but don’t really know how to evaluate a good business opportunity.

Then you get it in front of real customers and they hate it. Or they like parts of it but strongly dislike other parts of it.

If you’re lucky you’ll then go back to the drawing board and spend a lot of time correcting path. If you’re less lucky you’ll give up, soul crushed after spending all that time building something no one wanted.

Now wouldn’t it make more sense to test your hypothesis as quickly as possible, and then adjust course from the very beginning? Then when you build something, and invest your time and resources in it, you are confident that you are actually helping people solve some problem in a meaningful way.

My team’s idea started as an app where you could order an entire outfit from a brick and mortar store, like Macy’s, and it would be ready for you to pick up in under an hour.

We went to a shopping mall and tested some of our assumptions by talking to real shoppers. What we found was that very few of them wanted an entire outfit for events. If they were going to a party or out on a date they might need one new item, but buying a whole outfit wasn’t usually what they were looking for.

Now we could have stuck with our original idea, not listened to what people were saying, and tried to find customers that wanted this service. But such a service would need a strong base of consumers in order to partner with the retail stores. Instead we followed up with an online survey, and we’re glad we did.

We found a very different customer need arising in our survey and we found that need repeated over and over again. People wanted help finding a particular item.

Sometimes they were looking for specific shoes, or a yellow cardigan, and it took them a very long time to find it. How long? In the words of our customers “too damn long”.

So how about we help them solve that problem, and make it easy for them to find high quality results for whatever they are looking for. We decided to focus on one item at a time, since that more accurately reflected people’s buying habits and how they shop, and we made it a texting service so it was just like texting a friend.

The experience was a little humbling, but the insights we gained as a result of opening ourselves up to our customers was incredible. I’ve seen people attach their ego to their idea, and when you question the idea or give feedback they immediately get defensive.

These are the people who get rejected on Shark Tank. No investor wants to work with them and it’s no surprise why.

I’ve always been an idea guy and I too used to get really defensive when someone questioned or criticized my idea. HOW DARE THEY??? I came up with this idea in total isolation, and I’m a freaking genius!!

An idea isn’t you, it’s just a hypothesis. Test it, pivot as needed, and continue to move forward. Otherwise you and your idea will be left far far behind.

If someone takes the time to give you thoughtful feedback, they may or may not be right, but don’t get defensive. Instead really think about what they are saying, and if you think they’re on to something dig into it further.

Be curious. It just might improve your idea and your business.

2. Run your startup lean, especially in the beginning

Short of time, and with only a few resources provided to Startup Weekend participants like a free domain name, we didn’t have much. This freedom forced us to be creative, work with what we had, and communicate with real people.

Having money from the beginning can easily lead you to spend it in the wrong ways, and make your initial MVP (minimum viable product) costly before you’ve really tested it.

What can you do without resources? A lot.

You can create a business plan with the Business Model Canvas, you can do customer discovery, you can use your vision to inspire people to join your team, you can craft a pitch and pitch your idea to investors one on one or at pitch competitions near you.

You can raise a lot of money at pitch competitions. A lot.

And if you’re creative, you can also build an MVP as lean as possible. Even if it’s a skeleton of your future idea, build it, and then get it in front of customers. What do they love? What would they like to see added?

If you can answer these questions before putting money into your startup, you will be much better off. Spend money on a tested business idea, rather than just a hypothesis.

3. Face your fears and push yourself out of your comfort zone

Starting a business requires that you do things you’re probably not comfortable doing. I can check the box for both introvert and fear of public speaking.

Here’s what you can expect that weekend:

  • Talking to strangers.
  • Presenting in front of a crowd.
  • Putting yourself and your ideas out there for the world to see.
  • Form new teams and partnerships.
  • Take immediate feedback from mentors and other business owners.
  • Accepting rejection.

Coming into the weekend I already had some experience talking to strangers. I did some volunteer work which involved asking total strangers for charitable food donations for the homeless.

Doing that type of volunteer work also exposed you to a lot of rejection. Lots of angry people, busy people, and people who pretend like you don’t exist. You learn pretty quickly it’s not personal, it’s just people.

You also meet many very kind and wonderful people whose generosity inspires you. But, you have to get through the rejection in order to meet those great people.

The real gem is that if you can laugh at the situation, the people who violently avoid you are actually fricking hilarious. I love them.

So rejection was ok for me, but presenting is something I have been deathly afraid of. And for that reason I was the one among my team who presented. Naturally.

If you face your fears it will be uncomfortable but you’ll be stronger from it and you may even surprise yourself and give a pretty decent presentation.

I was inspired by my experience at startup weekend so I followed it up by signing up for an acting class and trying out for an improv troupe. It takes time to overcome these fears but just do it and be patient with yourself.

If I didn’t take up the challenge at Startup Weekend none of what followed would have been possible.

Wrap Up

In summary, I learned some really great things at Startup Weekend. The most important to me being:

  • Stray from getting too attached to your ideas and instead rigorously test your hypotheses.
  • Run your startup as lean as possible in the beginning.
  • Face your fears and push yourself out of your comfort zone.

If you’d like to try Startup Weekend yourself their website helps you quickly find one near you. The cost is very low and the value is very high.

Now you might be wondering where my startup is today? I’m happy to say it’s actually right here at where I have a fully functioning MVP.

Continuing to pivot and learn from customer’s needs, I built a chatbot to help the contemporary man find stylish clothes quickly and easily. It’s curated shopping, so you look great without wasting time shopping.

Check it out at and if you like it, it would mean the world to me if you share it with 3 men you know.