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Your alarm goes off.

5:30 am.


It’s time to get started on your daily routine, again. You stumble into the bathroom, turn the shower on and start your day. During your commute to the office, you caffeinate and listen to the same channel on the radio. At times you feel like you have a personal relationship with the morning show DJ. You arrive and depart around the same time (give or take) every day. You are a creature of habit in its truest form.

Your days are predictable, busy, somewhat structured, with little nuances and surprises in between. You have set processes that you follow, meetings that you must attend, deadlines that you must meet. There is a certain comfort you take in this routine, but you often find yourself wondering if there is more out there. What would it be like to start your own business or even join a startup? While leaving the comfort of predictability may sound scary to some, the thought of doing something more is intriguing.

I started my career working in larger, corporate-like environments. I went in every day, knew what I was going to be doing (for the most part), knew what success looked like and had a very consistent routine. While I would never trade my years working in that environment, I was often left wanting more. I appreciated the growth, training, and sense of stability that working in a larger company offered, but after almost 14 years working in corporate America, I decided to part ways. I moved from my very predictable life in Michigan and headed to San Francisco to join the other dreamers and work in startups.

Little did I know at that time that when I was driving my 2007 Chevy Cobalt across the country making that trek to Silicon Valley, that this journey would forever change my life. Silicon Valley is the land where hard work, dedication, vision, and grit payoff.

Before making that jump, there are a few things that you should think through. Startups are not easy but can be very rewarding. Also, not all startups are created equal. So what are the things you should consider before making that leap?

Self Assess

Being self-aware is tough. For the most part, what makes us unique and awesome can also be the same thing that holds us back. We all have operating states that feel natural and comfortable. The question is if you’re removed from that operating state, can you thrive? When I think of startups and what traits are key to have, I immediately think of the ability to adapt to change, grit, and operating well in chaos.

  • Change. How do you deal with change? Because guess what, startups change… all of the time! You may think that you deal with change well, but dig deep on this one. Imagine you worked for a month on a project. You put your blood, sweat, and tears into it. Then, all of a sudden, the company strategy changes. How would you deal with it? Evolution is core to startups. And evolution is just a nicer way to say “change”.
  • Grit. That may sound cliche, but do you have grit? There are generally no manuals that tell you how to figure out things. You will have to wear many hats. Google will be your best friend. Are you able to push through and figure out how to get things done?
  • Chaos. Does working in chaos excite you? No? How about helping take things that are not defined or in a chaotic state and operationalizing them for scale? If that sounds intriguing, you would have plenty to do. Startups are at times chaotic. Who am I kidding? Startups are chaotic. You have to embrace it and help solve the chaos.

The Company

Take a deep look at the company and how solid it is. Not all startups will make it. More than 50% of startups will fail during their first four years. There is never a guarantee that the startup you join will have a unicorn exit, so doing your due diligence is essential.

  • Founders. Who are the founders? Do they have previous startup experience? How do they manage? How do they set goals? How do they inspire? Understanding who the founders are and how they lead is crucial as this will impact you daily.
  • Funding/Runway. How many rounds of funding have they taken in? What’s burn look like? How many months of runway do they have? It’s important to know as much as you can about the financials when joining a startup. There are not many startups that are profitable out of the gate if you find one, great! But the reality is most startups are bootstrapped.
  • The Size. There are various size startups you can join. From early-stage seed days where there are just a couple of team members that are doing everything, to a much later phase, when things are more well formed and balanced. Research the difference and know where you’d fit best.
  • Employee Retention. People come, and people go. Sometimes it’s just a matter of a fit for the stage the company is in; sometimes it can be a matter of a bigger issue at the company. I often reach out to folks that have previously left to gather insights. When doing so, take the feedback you receive with a grain of salt. You can get some great tidbits but always know that there are two sides to every story.
  • Culture. You hear people all of the time talking about culture fit and culture in startups. Culture means something different to everyone. Make sure you know what it means to you. Make a list of values that are table stakes for you regarding culture. You will spend a lot of time with these folks. Culture is more than free t-shirts, ping pong, and happy hours. Culture not only dictates how everyone interacts in good times, but it also is a predictor of how everyone interacts during hardship.

The Product/Customer Base

Last but certainly not least, take a very deep look at the product and customer base you’ll be working with. Startups are not 9-5. You will live, breath, eat, and sleep the problems that the company is solving for. Make sure it’s something you can be or are passionate about.

  • Product. As stated above, find a product that you will be passionate about. There are so many startups that are solving for so many different things. There is no shortage of options. If possible, sign up for a free trial and play around with the product. What’s the experience like? Take it all in. This is the experience that the customers receive when signing up. Remember, in startups, the product should be continuously evolving. Talk to the company about their product roadmap and strategy. Moreover, if they don’t have one, that’s okay, ask them if you could partner with helping figure that out. That’s how it works in startups.
  • Customers. B2C, B2B, Enterprise, small business, and all of the other options out there, know who the customers are. You may not think of this as a qualifier, but it should be. It is essential that you are solving for a customer base that you are passionate about. You will spend a lot of time working with them.

If you do decide to join a startup, know that you will have stumbles along the way. Go into every situation with a growth mindset and a desire to make a big impact. Know that you will work hard, meet amazing people, and learn something new almost every day. Vision is always 20/20 when you are looking into the rearview mirror, but as I learned, the biggest risks at times reap the greatest rewards.