51 Brutal Lessons I Learned From Founding & Scaling My First Company
Read them so you don’t have to learn the hard way.
1. You cannot outrun a bad market. You can have a great product, great sales skills, great systems, and a great customer base and still lose revenue in a dying market.
2. If no one has ever done it successfully before, there is a reason why. Instead of wasting money trying to see if your “new” and “innovative” idea will work, save your money and don’t reinvent the wheel.
3. If you think someone on your team is a B player, you realize that they are actually a C player, once you hire your first A player.
4. Fire all C players on your team ASAP.
5. You will know within the first week whether you hired an A player or a B player. You can’t change them. They will always stay a B player. Cut your small losses and fire them, so that it doesn’t become a huge loss for you (money & time wasted).
6. If someone on your team is good at selling, it probably means they aren’t good at anything else. Keep letting them make commissions and revenue for your company. Don’t level them up into a leadership or management position. You’ll be trying to fit a square peg into a round hole.
7. When your company grows to $5 Million in Revenue and 20+ employees, you can no longer be a rainmaker and a CEO. You have to choose one, and then hire the other.
8. Business becomes 10x more complicated and sucks up way more of your time once you have two office locations. Make sure the business is worth your time to grow it.
9. Life is too short to spend time with employees you don’t get along with. If you can’t see yourself getting lunch with a potential hire, don’t hire them.
10. You will feel paralyzed, guilty, and trapped when the business is not doing well. It’s daunting to tell your team, but you have to leave your ego at the door, and tell them you f**ked up. If they are truly a ride or die, they will do whatever they can to help get the business back to normal again.
11. Unfortunately ride or die’s are extremely rare in business. When I had 42 employees at my peak, I probably had 2 ride or die’s, and they turned on my real quick when I decided to sell the business.
12. Employees only care about themselves and their future, no matter how much you do for them. It’s about them, and their satisfaction, not the company.
13. Don’t spend too much money on your employees. I wasted way too much money on making sure my employees were happy and satisfied with the culture.
14. Managing expectations is the #1 most important factor in business. How you manage your client’s expectations and your staff’s expectations will determine the success of your company. This is why you shouldn’t pamper your employees or clients too much when the market is good or when your company is extremely profitable. Because as soon as things turn, and you take things away, they will leave.
15. Find someone cheap to manage your email ASAP. I wasted SO much time on email. Email is the biggest time waster for a founder and can be easily outsourced by an assistant VA. Upwork is a great website to find cheap VA’s to help manage your email and calendar.
16. Never build a business for material or external reasons. Building a business has to satisfy you internally in order to keep you going through the immense amount of struggle you will face.
17. Don’t increase your expenses unless you have predictable, recurring revenue. Increasing monthly expenses while having unpredictable, up and down revenue was mentally jarring for me. If your business right now doesn’t have recurring revenue, then you need to find a way to implement it.
18. Pay for 2-3 mentors in order to get their perspective on all major decisions that you make. Peer mentors through Entrepreneur Organization and paying $500/mo for a seasoned business mentor saved me so much money and headaches.
19. Don’t rely on mentors or anyone else to make decisions for you. Pay to get perspective, but always make your own decisions after hearing different perspectives and insights.
20. Find a partner who loves you and supports you through the hard times and the good times. Having a supportive spouse on your side makes everything 10x easier.
21. If good employees are leaving your company, it’s your fault, not theirs.
22. Company culture is the most important component of a successful company.
23. One cancer cell to your company culture can spread quickly to your entire company, if you don’t fire that cancer cell quickly.
24. Promote slowly. Fire fast. Most founders (including myself) did the opposite and paid for it for years.
25. Cash flow will kill you faster than any competitor. I had quarters doing 7-figures in revenue and still scrambling to make payroll because AR and AP were misaligned by 45 days.
26. Hire a fractional CFO before you think you need one. I waited until we had 30 employees and burned 6 figures on tax mistakes that a $3K/month CFO would have caught in 10 minutes.
27. Lawyers are expensive. Not having lawyers is more expensive. Find one before you need one.
28. Most founders don’t actually need a co-founder. They want one because being alone at the top is terrifying. A co-founder dilutes equity, decisions, and vision. Only take one if they bring a skill you genuinely cannot build or buy.
29. You will romanticize the broke and scrappy days. Don’t. Those days were brutal. What you actually miss is the clarity. Recreate the clarity, not the chaos.
30. The skills that got you from $0 to $1M will not get you to $5M. The skills that get you to $5M will not get you to $10M. You will fire and rehire yourself at every level.
31. Most founders cap out between $3M and $5M in revenue, and the reason is always the same. They refuse to let go. Still in sales. Still in ops. Still approving every hire. The bottleneck is always at the top of the bottle.
32. If you are working 80 hour weeks past year three, your business is broken or you are. There is no version of long-term success built on burnout.
33. The customers you bend over backwards for will leave first. The ones you set firm boundaries with will stay for a decade. Pricing and respect are the same conversation.
34. Fire your worst 10% of clients every year. They take 80% of your time and pay you 5% of your revenue. The math never works.
35. Niche down further than feels comfortable. “We work with everyone” is the fastest way to be hired by no one.
36. Your prices are too low. I have never met a founder whose prices were too high. Raise them 20% today and watch what actually happens (almost nothing).
37. You will lose friends as you grow. Some will get jealous. Some will get left behind. Some will leave because you changed. All of it is normal. Make peace with it.
38. The founder who started the company is not the founder who scales it. You have to grieve the old version of yourself before you can become the next one.
39. Therapy is not optional for founders. The pressure compounds. The weight gets heavier. If you don’t have someone to unload it on, you will dump it on the wrong people. Your spouse. Your team. Your kids.
40. Your physical health is part of your P&L. Skip the gym for six months and watch your decision-making fall off a cliff. Your body is the engine. Treat it like one.
41. Don’t take advice from people who have never built what you’re trying to build. 90% of the business book bestseller list is academics and consultants reverse engineering case studies. Read founders. Listen to founders. Talk to founders.
42. The best advice comes from people two steps ahead of you, not ten. The legends have forgotten what it was like. Someone who just did it remembers every painful detail.
43. Don’t ever sell or walk away from your business out of exhaustion. Exhaustion makes every offer look like a lifeline. Sleep, take a real vacation, then make the call with a clear head.
44. Exiting your business will not feel the way you imagined. The week after it’s done is one of the loneliest weeks of your life. No team. No fires to put out. Just you and a bunch of free time you don’t know what to do with.
45. Your identity will get wrapped up in the company whether you want it to or not. Build hobbies, friendships, and a life outside the business now, while you still have the company to anchor you. You will need them later.
46. The number you wrote on the napkin five years ago will not make you happy when you hit it. No number will. Hitting it just resets the goal. Figure out what you’re actually after before you sprint another five years for nothing.
47. Most “overnight successes” are 10 year stories where you only saw the last 6 months. Adjust your expectations accordingly.
48. The founders you follow on LinkedIn and X are lying to you. Not maliciously. They post the wins and hide the panic attacks, the tax debt, the marriage problems. Assume 90% of the iceberg is underwater.
49. You will not understand how much you actually learned until five years after you walk away. While you’re in it, it just feels like surviving. Looking back, you became a different person.
50. The point of building the business was never the business. It was who you became while building it. Don’t shortchange that lesson by skipping the reflection at the end.
51. One of the most important jobs as a founder and/or leader at your company is to control employee’s egos. If you let them get too big, they will become a problem for your culture.
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Thank you as always for reading.
Much Love,
-Jason