23 Things I’ve Learned After 23 Months in Business

Published in

The Startup

7 min readNov 30, 2018

I try to abide by Ray Dalio’s philosophy of parlaying lessons into principles. In doing this the other day, I decided I needed to do a better job of keeping track of them. As one does, I thought, “I should write a Medium article about these.” The number 23 has no significance other than it being the 23rd month of business at the time of this writing.

23 months after starting Market(r) (https://marketr.life) where we use data science to build fractional marketing teams or stand up a company’s marketing team, I have hit a definite period of soul searching and reflection. It has been the most exhilarating time of my life, full of wins, losses, panic attacks, tears, and endless joy.

My friends mock my oft-cited line, “I’ll figure it out.” To me, that line holds a deep meaning. I firmly believe that my key survival skill is the ability and willingness to learn faster than I can fail. With that said, here are some key principles I have come to adopt.

1. Everything is my fault

At the end of the day, nobody else will take responsibility for my business. They may take blame for certain tasks, but it’s impossible for anybody but leadership to take accountability. You can delegate tasks, systems, and projects…but you can’t delegate accountability.

Bad client? You shouldn’t have signed them on, or you did a bad job of communicating. Bad employee? You shouldn’t have hired them, or you did a bad job of communicating. There’s a trend here.

2. “Manager-doers” are unscalable

There’s a time to do things that don’t scale, and there’s a time in which you shouldn’t do anything that’s unscalable. I’ve come to believe this is binary. Either be all-in on one or the other, then recognize the time to switch mindset.

Just today I was walking into the office a bit anxious about my long to do list. I then took a breath, centered myself, and decided to first divide my to-do list into those things that only I can do, and those that should be part of a process improvement. Next, I divided the process improvement items into the appropriate processes. Then, I communicated the process improvements with my team.

It took longer than it otherwise would have had I done them myself, but now I have a repeatable model for how to tackle these items, and I can focus on training others who have more time and energy to do it well than me. I then proceeded to conduct the tasks that only I can do.

3. Management type has to change drastically as the salary gets higher

You have to manage a $50,000/year person different than a $150,000/year person. I’ve gotten into debates with my business partner about this. He thinks I run the risk of micro-managing our remote employees who have more task-centered jobs. It got me thinking about the lines between strong feedback loops and involved training and feedback…and hampering people. Structure done right enables your team to produce at a higher level. Of course, we all know the perils of micromanagement. The higher the salary, though, the less structure you should implement and the more philosophy/core values alignment you have to work towards.

4. You’re never too busy

You always have time for the things that are important. Either you have your priorities out of whack, poor time management skills, or you just don’t care.

5. Clients finance our livelihood and they expect something for it

This is no secret, but it’s easy to overlook. They have no obligation to keep paying you. The selling never stops (see the next point).

6. Sales is the ultimate survival skill

Selling has a bad connotation. Ultimately, it’s just the transfer of enthusiasm; getting the receiver excited about what you want them to be excited about because they want to be excited about it.

Sales skills enable you to take risks, fire bad clients, and pivot faster because you can always go back to the well and get more cash in the door.

7. Cash is king

Cash flow in a business is like blood in the body. The point of living is not to just pump blood through your body. But if you don’t pump blood effectively enough, you’ll die.

The point of business is not to create strong cash flow. But if you don’t have healthy cash flow, the business will die.

This is not about revenue. This is about strong gross profit, net profit, and healthy amounts of cash in the bank.

8. If you’ve done everything you can, and you don’t see the likelihood of change, FIRE THEM and don’t second guess yourself

This goes for employees, clients, and vendors. There are only two reasons people don’t do their job right:

They don’t know how to, or
They don’t want to

If it’s the former, it’s your fault. If it’s the latter, it’s also your fault (see point #1), but you have the green light to end the relationship.

9. The panic attacks will pass

Just grin and bear it. It doesn’t get easier, you just get better at handling it.

10. Learn to enjoy the calm waters

The waters will inevitably get rough again. That doesn’t mean you should sit around anxiously waiting for the storm to come. When you get your ship through the storm, it’s a chance to build it back stronger for the next wave, prepare your crew, and enjoy what you’ve accomplished in the midst of the sunlight.

11. Every day is a new down and every week is a new drive

We get 7 shots on goal every week. All you can do is focus on the next hoop. Every Monday is a chance for a better drive. All you can do is focus on your next at-bat.

That’s a nested sports analogy right there!

12. Remember your early ambitions

I remember when I started, I would tell myself, “I just can’t wait until I can just work from a coffee shop in the middle of the day if I want to and make enough for my Ramen.” I got that relatively quickly, but suddenly it wasn’t enough for me anymore.

You should always be content. You should never be complacent.

13. You’re usually wrong

This goes back to “figuring it out.” Over time you develop the judgment to realize when you’ve locked in on the right answer and the confidence to assert yourself to the necessary stakeholder(s).

14. Your health will give out. Take care of that

I have increasingly bad acid reflux induced by my anxiety issues, haven’t been to the dentist in 3 years, bi-weekly migraines, and pre-diabetic blood sugar. I’m just now learning that I’m not invincible.

15. Growth is like riding a jet ski

If you go too slow, the waves will take you over because you lose control of your movement. If you go too fast, you’ll crash and burn. At the appropriate speed, you’re riding across the waves in full control of your every movement.

16. If you learn how to figure things out, then there’s no challenge you can’t overcome

I said this earlier but it’s important.

17. Pay your employees above market

There is no equal trade for time and money because time is always more important. Your employees are donating their most precious asset to your company, and their salary only allows them to offset part of their loss. Pay them well.

18. Money won’t make your employees happy, though

Money is a qualifier; it’s table stakes. The lack of money contributes to unhappiness. The presence of money only keeps the employee from becoming more dissatisfied.

There are a whole other set of qualities that contribute to job satisfaction. Read about Herzberg's Two Factor Theory.

19. Be slow to tell your team about your new ideas. It gets confusing.

I am prone to telling everybody I know about every idea that excites me. Over time I realized that it only muddies the waters to the recipient. They grow weary of every new idea and you develop a reputation for changing your mind frequently.

It’s important to pivot often, but there comes a time where you’re not the only one who needs to be bought in. Identify when you’ve personally experimented with something long enough to be able to get everyone else excited about it (see #6).

20. Be slow to bring people into your circle of trust. But once they’re there, take down all of your guards

It’s easy to get infatuated with people. Make sure to date your business colleagues slowly, then jump all in when you’re ready to tie the knot.

21. You can always get more done

Refer back to #2 and #4.

22. Pick management a system and follow it. It doesn’t matter very much what the system is

We follow the Entrepreneurial Operating System (EOS®). In fact, one of our advisors, Mark Leary (leary.cc), is a professional EOS implementer.

The worst thing you can do is change your management system with the seasons. Pick one and follow it religiously. I prefer EOS®, but there are a lot of good ones.

23. Everybody wants to give you advice and most of it sucks. You should listen anyway

You can learn something from everyone you meet. Don’t let their bad advice get in the way of you discovering what that lesson is.

Reach out to me at tristan@tarpleyholdings.com! I want to meet you. Check out what we’re doing at marketr.life. Hope you enjoyed.