32 Startup lessons

Things I’ve learned & observed while working at a company that’s hired 130+ people in 4 years.

Chad Engle
7 min readFeb 23, 2015


I’ve had the pleasure of working at a rapidly changing startup since 2011 (BoomTown), coming on board as employee #38. Things have changed, teams have formed, products have shipped - These are few things I’ve learned & observed, in no particular order.

  1. Change is the only constant
    Everything can and will change. Teams will grow, products will shift, roadmaps will be scrapped, desks will move, people will be hired, fired, promoted & demoted. Change, is the only thing that stays.
  2. Hire for culture first
    This is a huge one for us at BoomTown. We have culture interviews for every candidate that comes through the door — making sure they meet the entire companies values but, also the immediate team they’ll be working with. You can always build skills over time but, you can’t always build the teams acceptance of someone who isn’t a fit.
  3. Build teams on shared fundamentals, standards or core values
    Everyone knows what “good” is. Everyone knows what “great” is but, unless you define what “our great is”, everyone will not have the same quality bar. Once you’re on the same page, everything comes easier. Even better is when you have a common goal that’s influenced by the entire company — helps everyone understand what needs to be built, supported and sold.
  4. Be open & honest
    By being open with each other, you know exactly how everyone feels and there’s no gray area. Without that level of trust, it’s hard for everyone to focus on creating meaningful work.
  5. Ask for forgiveness instead of permission
    We call this “go for it” here. We hire smart people who are able to drive the future of the company. If you think something is going to drive the overall business goals of the company, step up and do it. Don’t sit around and wait for someone to tell you what to do.
  6. Reach out and take it (Carpe Diem)
    In start-ups there’s rapid amounts of growth as well as unknowns. There’s no checklist for how to make something new. You either seize the day or, nothing happens. Write your own path instead of letting it come to you.
  7. Know when to press (Not Friday at 3pm)
    Hustle. Know when you’re in the zone and when to stay with it. Starting something new at 3pm on a Friday? Not good. Hammering late on a Tuesday? Better. Find your cadence and make sure you work your days around that.
  8. Know when to fold
    Pace. This seems like a weird word for a start-up when you’re supposed to be in hustle mode 100% of the time but, without pace, you burn-out. When you burn-out, you’re not at your best. When you’re not at your best, you’re not helping the company. Take a break when you need it and then get back to hustling.
  9. Cross collaborate & pollinate
    There are bright people all around you that are working on the same business from different vantage points. Listen to their pain-points and things they’re solving, you might get some great insights by just being around people of other walks of life.
  10. Stay humble
    Each piece of the company puzzle is needed and it’s easy to think “Without X, we wouldn’t exist”. It’s more like, “Without any of the pieces we wouldn’t exist”. Take out one team and the whole thing falls apart. Don’t let titles and accolades go to your head.
  11. Not everyone is good for the company, forever
    There is such a thing as the old guard. Some people thrive in 10–20 people companies, they’re generalists that are good at everything so that’s where they make a lot of impact. Once the company gets more specialized, it’s perfectly normal for people to move on to other areas in life. You can’t expect everyone to live in the same company forever.
  12. Put your time in people
    The work will come and go, even if you put in 3600hrs into a project it doesn’t always mean it’s going to pay out in the end. The company could pivot and then you’re out 3600hrs. However, putting your time in people always pays off.
  13. Listen
    Don’t open your mouth until you hear the other person out. I know you have a point to make but, the person you’re listening to might make it for you though. Not everyone is a great verbal communicator and if you don’t listen to what’s going on, you might miss it.
  14. Listen again
    Always have your ears open. There’s so much that can be learned by hearing peoples wins, losses and strifes.
  15. Nostalgia can be poisonous
    I used to know everyone here” “everything is always changing”. There will be a point where you don’t know everyone and can’t even find where people sit. Is it bad? No. That’s what happens with growth and huge success. Make sure when you take a trip down memory lane, it’s not because of the wrong reasons and if you misses pieces of the good old days, find ways to recreate those pieces.
  16. Onboarding is crucial
    You can’t expect everyone to come in and hit the ground running. Things have evolved and changed so many times before a new hire comes in, they might start down a path you just finished that didn’t pan out. Letting people know how the company operates, how things are completed and the “code of conduct” is crucial to them succeeding.
  17. Take a walk
    Can’t solve a problem? Stuck? Burnt-out? Get up and move. You’ll find some one on the way to the coffee machine or see someone else doing something amazing or at the very least, get some blood flowing through your veins and help you get back into solving the task at hand.
  18. Get out of the office
    There’s no rule that 1:1's, meetings or other work functions have to happen inside the companies walls. Sometimes just getting out and grabbing a coffee, beer or lunch makes all the difference in getting to know someone. A lot of people think “I’m working” and without breaking the mental thought of being “at work” it’s hard for people to open up, and think outside of their tasks.
  19. Take time off (there’s never a “good time”)
    Let’s say it together — Vacation. This ties into the rules above of knowing when to press and when to fold. You have to make time for yourself. There’s always something to-do but, that stuff will be there when you come back and if it’s not, it probably wasn’t that important anyway.
  20. Put in some extra hours
    Be the “spirit animal” pitch in and stay late with your team or another team. The amount of rapport that’s built by going through something tough as a team than just a typical work day is amazing is completely worth it. I’m not advocating doing this week over week but, be conscious of when putting in the hours will do more than solve the task at hand.
  21. Make people laugh
    The teams that have fun together are the ones that make the best work together. If you’re genuinely having fun on a project, days and hours melt away and you’re only focused on the outcome.
  22. Trust your gut
    Spidey-sense, 6th sense, intuition — whatever you call it, trust it. A feature feel off? Speak up. An potential employee doesn’t quite mesh? Speak up. Does the data speak in the opposite direction you know will work? Learn when to trust your gut vs. being influenced. Because most of the time, it’s right.
  23. Find people who make you better
    Look to work with people who are smarter than you, more talented than you, more experienced than you and challenge you to raise the bar. If you’re not constantly being challenged and pushed, how do you hope to learn & grow?
  24. Prepare for burnout
    In a fastpaced start-up, 3 weeks feels like 4 months. You will get burned out. Accept it and instead of trying to ignore it, learn how to reset yourself. Do you need a couple days out of the office? Do you need a full-fledged vacation? Maybe it’s as simple as taking a half day off… Whatever it is, learn what helps you bump the rest button early.
  25. You will be frustrated
    Just like you have to prepare for burnout, you should prepare to be frustrated. With so much change, you’re going to spin your wheels, fail on a project, get wrapped around the axel or see something go a different direction than you expected. Don’t dwell on it and learn from it.
  26. Disconnect from it all
    There’s nothing better than taking an entire weekend where you do not even think about looking at a piece of technology. If you haven’t learned to do it yet, give it a try.
  27. Make time for yourself
    If you’re not living your life, your life could live you. You have to make time for yourself otherwise, you’ll look up and it’s 2 years later and you still haven’t taken a vacation or picked up a new hobby. Don’t let your job/career take up every second of your waking life.
  28. Learn to say no
    I can’t stress enough how much being focused makes an impact on your life. A great example is 37signals. They recently focused on their product bascamp — so much so that they are now named basecamp. By focusing yourself and saying “no” you can be more productive on the things that matter.
  29. Focus on your work
    Politics, red-tape, rumors, news, it all comes with the territory. Focus on what you’re here for: the work. Don’t let the other stuff bog you down or take up your mind; there’s 33,000 crappy reality TV shows for that.
  30. Measure, Measure, Measure
    Make sure with every project that there’s something you’re measuring. Visits, leads, contacts, bounce rate, sign-up rate, time on site, retention, something. If you don’t know how a project or feature performs, how will you ever know if it’s a success of failure? But also, go with your gut.
  31. Lead by example
    Want to raise the design bar? Do it. Want more people to chip in and clean up the office? Do it. Want to have a culture that’s not silo’d? Make it happen. Yes, you’re one person but, all it takes is one.
  32. Dream big
    What fun is dreaming small in little tiny things that you know you can do. The only way you grow and learn is getting outside of your comfort zone and the only way that happens, is dreaming big.

Thanks for reading this — If you found value in this hit the Recommend button. If you didn’t find value — call me out here: @chadengle

P.S. — Want to work on shaping the real estate industry with a ton of passionate people?? We’re hiring at @BoomTownROI.



Chad Engle

Designer, Maker of Things | Design Director @GoDaddy