Why I Quit* the Startup Life

Alex Ryan
Alex Ryan
Oct 21, 2015 · 7 min read

*I didn’t really quit. I just wanted your attention.

But this Fall I had a choice to make…

After an 8 month journey serving on the founding team of my first startup, I had to make the hard choice of ending the journey. I wasn’t a co-founder, but I was close enough to experience much of the same rollercoaster that founders experience. Here’s my reflection on the last 8 months.

You don’t learn from failures… you learn from reflecting on failures.

I don’t think we’ve met…

If we haven’t met yet and you’re jumping in at the end (hint: right now), take a peek back to the beginning. Since then, I’ve started school at Georgia Tech in Atlanta pursuing a Master’s in Human Computer Interaction (HCI). It’s only a couple of months into the school year, but already so many doors have been opening. And I want to take advantage of them.

Since startups and balance are two ideas that don’t go well together, I had a choice to make — startup or school. At the start of the journey eight months ago, I had only a vague grasp on what makes a startup successful. Living in the startup world has taught me a lot — from pattern recognition of what qualities make a great startup to working in a real-world team. Although I had a great experience overall, here’s a couple of lessons on what I learned not to do and why I made the decision to prioritize school at the end of the day. (at the end of the day, I also learned a little about what to do at a startup as well, but that’s for another blog post).

~ lessons ~

let’s get rich

Ahhh, money. Want an idea of how important this is in the venture world? Watch an episode of Shark Tank. From the outside, investors rarely seem to be concerned about the product — they always want to hear about its potential to make money. But, it’s important to keep some perspective when you start out on the “next big thing”. The chance you make it to a billion dollar valuation is


The odds aren’t great. And if you’re in this to make money, you’re better off with the typical 9–5 job. But I digress.

During my personal startup experience, money came up a lot. And you could always feel some tension when it did. Unfortunately, the first conversation I had with the team revolved around how much money we’d be pulling in by the end of the year. Maybe money isn’t the best thing to focus on in the beginning…

Lesson 1: When the team is in it for the money, that’s a red flag. The product always comes first.

Looking back, our team’s motivations were in the wrong place. Execution on the product should always be number one.

slicing the pie

As someone that loves numbers, learning about equity was actually a ton of fun. Everything from dilution to preferred stock to valuation to a pay-to-play provision was brand new to me. Thanks to Venture Deals by Brad Feld I picked up on these terms pretty quick and was finally able to understand the deals thrown out by the sharks in Shark Tank.

In real-life, equity is a tricky topic too. If you’ve never personally had the equity conversation, listen to episode 3 of the Startup podcast — really, go listen to it. As you’ll discover, it’s a really touchy subject that very few people are comfortable navigating. I had no idea what I as getting myself into when I brought it up.

Lesson 2: Don’t shy away from the equity conversation. The sooner you work through it as a team, the better.

At the end of the day, equity divided our team. It hurt people’s feelings and eroded established relationships overnight. No one felt like the resolution we came to was fair. The equity conversation can quickly turn from rational to emotional.

Maybe it was because none of us had ever had the conversation before or maybe we thought everyone was on the same page in terms of the value each team member provided. Regardless, our inexperience hurt us and who knows what an experienced entrepreneur would have thought about how we worked through it.

We probably didn’t know as much as we thought we did.


Communication is kinda important. Big companies can get this wrong and maybe lose a little efficiency, but in the startup world you will eventually lose the whole venture. There’s just no way around it — communication is vital when you’re moving as fast as you need to in a startup.

Lesson 3: Just because you downloaded Slack doesn’t mean you’ve got great communication on your team.

As the sole technical member, there were a couple of key channels of communication that I needed and had trouble figuring out. The most obvious gap was on product development. In the startup world, it’s tempting to forgo processes to make things easier on yourself and to move quicker. But, when it comes to product development, that can only last so long.

When our efficiency in moving things from ideation to production started dropping, we formally adopted a simple SCRUM process and started developing in Sprints. This worked great and moved everyone onto the same page. While we got our short-term planning working, our long term planning never came together. We never had a written roadmap with checkpoints built in to assess our progress. Consequently, I had little idea of where we stood with the product and how far we had to go for important milestones.

There were other communication issues as well on the team — Slack was never used effectively by all team members, pay would start/stop/change without warning, and transparency on the health of the business was lacking. The founding team members shouldn’t be kept in the dark. Next time I’ll be able to catch this and address it with the team earlier.

building a team

The team is everything. A lot of the time you’ll hear that investors aren’t investing in the product, but investing in the team. Build a great team and you’re well on your way.

Lesson 5: Ideas/products change as you pivot, however the team is one thing that will always last.

Want to make someone feel like they’re part of the team? Value them. Celebrate what they do right and help them work through what they got wrong. Personally, I struggled to feel valued and that’s really unfortunate.

Thinking back, it’s hard to value someone if you can’t value their contribution to the team. And I think this is something we struggled with. As the only technical team member, no one else could really get an idea of what my contribution was and so, naturally I would most likely be under or overvalued. I took newborn ideas and brought them through the entire design process all the way into production- I might have technically been an adopted parent of the ideas, but I really felt like I was the parent.

Someone else birthed them, but I raised them.

Here’s what Sam Altman — president of Y Combinator told his class at Stanford:

There’s this weird thing going on in startups right now where it’s become popular to say, You know what, we don’t need technical cofounders, we’re gonna hire people, we’re just gonna be great managers. That doesn’t work too well in our experience. Software people should really be starting software companies.

Regardless, there was no authentic team feeling once the going got tough and I sometimes felt like I carried the burden of the team as the only technical member.

And I felt disposable. That’s not healthy for the team.


At the beginning, startups have very little — a $0 valuation, a couple of chairs, a handful of crazy people and an idea or two. But one thing that they always start with on day one is culture.

Lesson 6: Hanging up a handful of your favorite motivational posters doesn’t count as culture.

Maybe you care about culture, maybe not. But for me, culture is incredibly important and one of the first things I plan on looking at before accepting my first full time job after school.

I want both a culture of excellence and a culture of celebration.

Unfortunately, our culture never really developed past the first couple of weeks and thus, we lacked that glue that culture provides a team.

Culture takes a lot of work to develop, refine, and to embed in the hearts of your employees. Similar to your vision, it should be introduced, repeated, repeated again, and then repeated one more time. It provides a framework from which you make decisions and interact with customers and coworkers. When done right, culture pays off.


But it’s an investment that pays off in the longterm not the short term.

what’s next

Now that I’ve made the decision to focus on school, I should probably start getting on top of my homework. I’m excited to see the opportunities that open up and to learn more about user experience design.

It’s been a wild ride and I’m so thankful for the chance I got to join a startup. I got to get a peek into what it takes to build a company and got to build an entire iOS app from scratch. It was an incredible experience.

Got a similar experience? I would love to hear about it. Add it below or shoot me an email (thomas.alexander.ryan@gmail.com) and let’s grab coffee in Atlanta. I would love to meet you.

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