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Lessons Learned Starting My Own Business

Warning: This post will not be backed by any research and the findings are based purely on my own experiences. The following are what I feel are the most important lessons I’ve learned so far. Take them for what they’re worth.


Focus on Finding the Right People Early
I got a good piece of advice very early on that, out of stubbornness, I chose not to apply for quite a while. When you find yourself spending a lot of time doing stuff you’re bad at, find somebody to help. You can’t do everything yourself. At some point, you have to admit that you need help and go get it. Spared was spinning its wheels for at least four months after my co-founder and I decided to actually go after building this business. We had a dream and a loose idea of how we would make it work, but only a subset of the skills required to do it. Spared is ultimately a technology service, and neither of us had the skills to build it well ourselves. We needed help. We needed skilled and passionate people to join us on our mission.

We agonized over the decision of whether or not to outsource development for far too long. It seems that online opinions on this are split on this matter (outsource vs. in-house), but in our case I’m SO thankful we decided to recruit and hire an in house CTO. First, because our CTO, Kenny McGarvey, is an absolute wizard. We’re so lucky to have him. We went through hundreds of applications and dozens of interviews to get there, but it was absolutely worth it. Second, because what the hell were two guys with limited tech knowledge going to do with an outsourced app? Pay for and take delivery of something we were completely underprepared to maintain and improve upon? I’m sure there are plenty of applications where this is realistic, but ours isn’t. We’re dealing with a lot of sensitive information. It sounded like a recipe for a crappy version 1 that stayed that way until the company failed.

Our second hire was our Chief Creative Officer, Kathryn Reina. Kathryn is a designer AND front-end developer so was an amazing find! As you can see on the surrounding website, she’s a total stud. I was responsible for design prior to bringing her on board, and I was in no way qualified. Lacking any education in basic design principles, I consistently turned out garish assets. I occasionally sought refuge in minimalistic designs (Apple does it, so why can’t I?), but, truthfully, it was only out of frustration. Let me assure you, owning SketchApp or the Adobe suite doesn’t make someone with a bad eye and no skills any better.

Finally, we brought on our CMO, Laraine Wilkinson. Compared to my own meager experience in marketing, Laraine brings nearly a decade of successful campaigns to the table. To say I thought marketing just meant throwing money into promoting posts may be a little too simplistic, but I certainly didn’t have her insight or organization skills. With Laraine on board, we finally had a well-rounded team. It felt amazing!

Know your strengths and weaknesses. Focus on your strengths and find other people passionate about your vision that can fill in the gaps. I cannot emphasize the importance of this enough.

Seek Out People Who Will Tell You NO
This is a big one. When you first have your idea, you’ll be sure it’s the best one ever. It’s your baby. You know who else knows that? All the people you’ll pitch it to first: friends and family. You won’t be able to contain the excitement in your voice. You’ll ask leading questions (“This is a good idea, RIGHT?”). People will tell you they love it because they love you. You won’t want to leave that positive feedback loop, and you’ll keep going back to them to get reassurance that you’re on the right track.

Don’t do this. You need to find the people that don’t like what you’re doing or think it’s a bad idea and find out why. It may be a simple fix. It may be a glaring hole in your business model that you overlooked in your excitement. Whatever it is, the NO people will help you find it. Seek them out and let them rip you apart. It’s good for you.

Be Prepared and Willing to Buckle Down Financially
Starting a business costs money. Bottom line. You may have development costs, salaries, marketing expenses, etc. Want to work on it full time? You may have to quit your job. It’s pretty scary, and looking at your financial situation becomes anxiety ridden. You’re acutely aware of how much money you’re putting in and how much you have left before you’re just broke. As the owner of a startup, you’ve got to start rethinking all your spending habits. The business must be your primary financial focus so your habits need to reflect that. Get comfortable saying, “Honey, we can’t go out to dinner.”

Cultivate Balance
I’m a binger, so this is a tough one for me. And I’m not going to feed you the line of bullshit that it’s only, “I can’t stop working.” It’s not just that. I binge in every direction. I’ll work like a maniac for two weeks, then fall down a rabbit hole owned by one of my many vices for days if I’m not mindful about how I spend my time. I’ve got to get small doses of my vices mixed in with my work to protect against this. I’ve got to schedule family time or I’ll let it fall by the wayside. It may be different for you. Just know that owning your own business will test you here in a way that no 9 to 5 ever will. Make sure you find time for the things you care about outside your business.

I’ll keep posting about the lessons I learn as we continue to grow. If you have any specific questions, you can email me at I’ll do my best to answer thoughtfully and in a timely manner.