. @YesOptimist by the numbers:

- 4 years in business
- $3,333,686 in total revenue to date
- 24 core team members
- 40+ in our freelance network

Here are my learnings from 2020.

(Thread)

2/ First, COVID was a challenge. (duh)

Like many companies, we saw a lot of uncertainty and an impact on revenue.

But, honestly, we were fortunate.

3/ Working primarily within tech and startups, most of our clients were less impacted than other sectors.

But we still spent most of our year under our revenue target of $125k/mo.

4/ Lesson #1: There’s no easy button for entrepreneurship.

There are hard things.

There’s responsibility—to clients, to teammates, to partners.

Even with our weird company structure & no FTE, my actions and decisions have real impact on people's lives.

5/ This was apparent when we lost clients due to the pandemic.

We didn't have enough work for everyone. It was hard to let people know that the money wasn't there. I want to help everyone, all of the time.

I can't.

6/ Lesson #2: Growth can be the safest bet.

Our original goal for 2020 was to hit our target revenue of $125k and remain that size indefinitely.

Instead, we shrunk.

7/ We turned away some opportunities because we were “full.”

Of course, those opportunities then moved on, which led to down months when we later lost clients. Then we would be hungry for new work and take on too many clients at once (6 in 6 weeks!)

8/ Staying "small" seemed like the safe bet originally. But, w/ uncertainty, it was actually the dangerous choice.

Instead, we need to structure the biz to grow beyond where we are now and fix the bottlenecks that prevent us from taking on clients at a more predictable cadence.

9/ We've developed a queue for onboarding new clients based on signed contracts, with a paid invoice reserving the spot for future kick-off and strategy work.

10/ Lesson #3: Every client will leave, eventually.

Related to the previous point: We must plan for the inevitable reality that clients will leave us for one reason or another.

11/ We are fortunate that our clients generally work with us for nearly 2 years, on average.

But that doesn't make it any easier when things change or they decide to hire internally vs outsource.

12/ "The day you sign a client is the day you start losing them."

13/ This, of course, seems scary—even pessimistic. But it's the truth.

& if we know this is the truth, then we can plan and be strategic about how we run the company. If clients will inevitably leave, we need a predictable pipeline of new clients to offset that trend.

14/ Lesson #4: Delegation doesn't solve everything.

Instead of simply trying to chop my job into a million pieces, I need to actually replace myself. As in, hire someone else who can fully own the client strategy.

15/ That's why we've been hiring content strategists to join our team—and provide deeper ownership over each client engagement (vs me trying to half-manage 15+ clients at a time). https://twitter.com/TylerHakes/status/1335584461191340036

16/ Truth is, my own ego prevented me from doing this sooner.

I felt ownership over our work & felt like I was the only one capable of delivering at the high level our clients expect.

This was stupid and short-sighted.

17/ I want to build something that's much bigger than myself and my ego.

(Still hiring btw, if you're a great strategist with content + SEO chops & enjoys talking to clients!)

18/ Lesson #5: Use the business cycle as an advantage, not a roadblock.

We plan every quarter, & most times our content planning process sits on top of other work. It's stressful and consumes my whole life for ~3-4 weeks at a time.

19/ Earth to Tyler: Stop planning other work during that period.

Seems obvious.

Only just began implementing this way last quarter.

20/ Plan internal projects, other work (outside Optimist), & personal time around the quarterly schedule.

Plan out individual projects as sprints that can be completed in ~1-2 weeks.

Get them done before the planning cycle hits.

21/ Our plans for 2021: Build a truly scalable model.

Take over the world.

We've lifted our previous goal of $125k MRR. I think we could 2x — $3MM ARR — this year.

22/ We consistently generate 2-3 high-quality inquiries every week.

We do a pretty good job of actively disqualifying those who aren't a fit.

With the right team in place, it wouldn't be a stretch for us to beat any goals we set today.

23/ It's going to be a fun year. Look forward to sharing updates & progress as they happen.

Thanks to the team for their work.

Thanks to my wife for her patience & insight.

Thanks to y'all for reading these tweets.