My life the last six months has been consumed by two activities: training for a long bike ride and trying to help get a startup profitable. I’ve been surprised to learn that I can take lessons learned from each and apply them to the other.  So I present (with no commercial interruptions) three lessons:

Know your limits going in and don’t change them

When you get on your bike for a training ride you have to decide how much stuff you want to take with you – the more stuff you take the harder the ride is:

  • 1 or 2 water bottles? Will there be more water down the road?
  • 2 spare tubes, CO2 cartridges? wrench? phone? credit card? spare bike? cab fare?
  • food: gu, Honey Stinger, chicken biscuit, rack of ribs, hot pocket? (or all of the above)

Once you get on the bike to do a 30 mile ride you can’t easily decide to do a 130 mile ride as you will run out of food, water, and daylight.

When you decide to take on a startup as a founder or an early employee you have to decide how much risk to take, and it’s not a good idea to suddenly change that risk equation during the life of the startup (as you most likely will be tempted to do so):

  • Pay: how much equity vs. raw salary? How long can you survive on a lower salary?  (Are you willing to switch to cheap toilet paper?)
  • Time: What are you giving up: sleep, family vacations, taking the family to the zoo on Saturdays, hobbies (what you used to do before you had kids), time for friends, time for extended family, time to read a newspaper or cereal box, time for TV (How many seasons of Jersey Shore are you willing to miss?)
  • Opportunity: how long are you willing to go and say ‘No’ to every additional job/opportunity/sudden trip that comes along during your tenure at the startup?

You can’t take 70% of your salary with massive options vested in 4 years and then run out of money for skittles 2 months in. And when the company tells you that they can now only pay you 60% of market you shouldn’t try to make it work as you will, just as in cycling, run out of food.

A better way to say this that works for both: you and your family should know the terms/conditions going in:

  • I’m going on a 120 mile training ride and will call you at mile 60; I’ll be home and showered in time for dinner.
  • I’m working for a startup for 6 months at 80% of market rate, I will work normal hours and from 10:00PM until I go to sleep after everyone else, doing it for experience, do not expect options to ever be worth much, we will reassess in August.

Getting your rules of engagement out in the open makes you not get lost in the excitement of good weather, good market conditions, or temporary good feelings. And this, my friend, brings us to the next point.

No matter how good or bad you feel, it won’t last

This is a very common saying in endurance racing and is quite effective in calming nerves during a monster event. I have experienced the thrills of riding my bike for eight hours and feeling completely invincible only to feel like I should call an ambulance 10 miles later. In my experience on long rides you start out feeling good then go through period in which you start to feel crappy and doubt why you are doing the ride at all. As the ride progresses these good/bad periods start to jump back and forth and the highs get higher and the lows get lower.

There are parallels in the startup world. For the first month building something from scratch you will feel great – no HR BS, no this no that, no limits. As you crank out code rather than sleep or see your friends you will let doubt creep in and wonder if your rules of engagement need to be adjusted. You will go through lows unlike anything you can experience at a big company. Short of rare events, you simply can’t have the same feeling as you do at a startup where you need to complete a feature of fix a bug for a demo the next day or *almost literally* you will lose big – let your partners down, potentially lose you and your partners money, and perhaps lose friends all the while having spent massive time away from those you love in order to execute your failure.

That being said, the highs at a startup are higher than anything you can do in a normal employment situation. Seeing a famous company use your application, getting chosen as a key partner, watching as an on-the-fly demo with a famous person goes crazy smoothly (all with software you wrote last week), watching the revenue numbers grow, watching as people go from beta to entering their credit cards, watching as customers start complaining because they see value and *want* what you are building. And of course the biggest high of all – the potential to make more money in a few years than you could in many more than a few years.

These highs and lows need to be tempered just like in long-distance riding. Sure – we are feeling good now but let’s still stop and eat and refill water while we have the chance. Ok, this looks like it’s working but let’s hold off on doubling-down on equity or buying that new mobile margarita machine just yet.

Embrace being different and enjoy its rewards

And, of course, the first similarity that struck me was this: you need to embrace the consequences of doing something different.

Cycling is a weird sport. Very, very tight clothing, little of the professional sport on TV, lots of tension between driver and cyclist, an unmanly image, and a big upfront cost (the bike) keep most people away from it and in company softball leagues and on their couch. But if you move away from what the “masses” do you will find bigger rewards – cycling trains your heart to recover unlike any sport, you get to travel massive distances that you can’t in other sports, you get to climb mountains that stress your car, you get to feel the raw joy of going fast that reminds you of flying, and of course, you get the simply joy of feeling that you were meant to move.

Working at a startup is also weird – isn’t a job sort of about getting guaranteed money on a frequent basis? Sure, but only at a startup can you feel what it means to create something from nothing. A startup is a no excuse situation – no I’m-the-only-one-who-cares, no blaming teammates, no blaming corporate IT policy, no reason to be any slower than the fastest you can be. And in that situation you will learn and move faster than you thought possible.  And only in a startup can you really feel that you were meant to create.