I shared a version of this with my company today, and wanted to make it public.
I was recently listening to an interview with a smart micro-cap investor on one of my favorite podcasts about value investing (as well as the occasional lamenting around big tech valuations and Bitcoin). One of these dudes discussed how he looks at the management teams of companies. Something in his framework struck a cord with me, I won’t regurgitate the story well, but it’s well enough for my purposes. The story he told was that some CEOs can lead a team, grinding out revenue growth and build a $50M company, but they become the bottleneck, they become the company’s ceiling. These CEOs are very cool, but they kind of white knuckle it, which doesn’t have scale. His investment thesis involves identifying companies that can blow past the $50M mark and become $250M and $1B companies. One of the ways he gets there is by finding a CEO who has surrounded him or herself with brilliant managers (we've got some of those), advisors, and directors (and from my perspective meritocratically arranged vs the hub-and-spoke configuration most companies use).
This resonated with me and tied back to the countless books I've read and interviews I've listened to around growing a successful and impactful business... as well as my personal experience. It touched on the frustration I've felt recently as I've set some lofty goals that I aim to accomplish but haven't had the time or space to get sufficient momentum on our side. I've created my own inertia.
Here I will address the problem and take the first steps at repairing it.
What's the problem?
I'm too involved in everyones' work, tasks and slack threads. Our team is totally awesome. They don't need (or want) me up their butts. I spend so much time following up, sticking my nose in slack threads, and pinging. This is a function of a few things:
Culturally, I was raised to be busy with a bias towards action and I often feel guilty to think for long periods, write, or research/study because I don't associate it with "doing." This is obviously a cognitive failure.
I'm impatient, I want to see everything done, yesterday and fomo because what if it isn't done at all?
I'm controlling. Even though, from my perspective, everyone is able to operate truly autonomously, my controlling nature keeps me on the followup and contribution path.
I battle the cognitive failure of recency/novelty bias. I have so many ideas and thoughts every day, I write down maybe 50 ideas over the course of a day, every day and then I work on them myself or with the team. I've done a poor job clearly identifying just a few priorities and sticking to them. Working through my massive daily task list that never actually gets shorter is a problem I've continually created for myself over my decade and a half in business. I admire successful people that have a ton of space in their schedule to do the big and impromptu things.
These failures don’t allow me time to work on the biggest things.
What are the big things?
The big things are the high-value inputs into the business that I want to spend more time on. The value of me hiring someone awesome in our organization is a much higher leverage activity than me doing that work and spreading it out among the team. Here's where I want to invest my time now (these things change as the company and I evolve):
Scheduled, deeper, organized (or unorganized thought). I need to stop, read, write and think more deeply and strategically about the things that are important to us and the path to get there.
Continue hire the right people, and put them in the right seats.
Build a board of advisors and directors that have gone farther than I in places I haven't that are also cool humans and drink their milkshake (like sticking a straw in their collective brain).
Raise money. We have done a good job with retail. Starting more institutional and high net worth conversations will be good for us and help elevate our game to get us to a place where we can hire more cool people, more quickly via better habits and more capital.
Measurable outputs (how we know if I'm doing a good job): we’re growing (revenue), we’re building (product) and we’re eventually publicly trading.
What is my job?
My opinion of my job is to:
Set strategy
Set direction & course correctCultivate culture
Hire badasses
and get out of their wayKeep money in the bank
Measurable outcomes: The way we can measure my effectiveness is with sustainable revenue growth. That's my KPI and by that measure, I have a lot of room for growth. Another measurable outcome is the happiness of our team, borrowers, lenders and investors. As to the team, something will be announced by a certain magazine as early as next week. Now to scale it.
How do I evaluate what to work on?
Like with most things, I intend to ask myself some fundamental questions including:
Can I do this in 5 min or less?
Get me some cheap dopamine.Can this have a big impact?
Block 2 hours for it and do deep work.Is it part of our priorities?
If it's really cool, and off-focus, it's off the list.Can I reasonably delegate this?
Is this a more appropriate job for someone else vs for me?
Honestly, I think these are questions we should all ask, frequently.
My immediate action items:
I will make space in my notion board, slack and schedule. I hope the team will help hold me accountable to this as my tenancy will be to revert to my mean and I want to go beyond that. Please make suggestions, comments, etc.. for where I can be thinking better or differently. I want to improve for us.
Slack
It is a beautiful place to collaborate. I will mute some channels and do my best not to stick my nose in other peoples' business unless it's specifically and directly requested. I will remain at everyones' service but I will not be reactive to every conversation and be better at high level feedback and occasional final approvals. Keep toasting eachother, keep momentum going. I'm there, just less trigger happy.
Management
I will elicit the help of our team and leadership and delegate without micro-managing. I will assign less and focus on directional priorities.
Priority Setting
I will focus on setting just a few priorities and sticking to them so we don't get pulled in too many directions. Instead of following up on individual threads and tasks, I'm going to keep my eye on the big priorities for the quarter and the year and work to ensure the team is aligned on those.
One on Ones
The goals of my regular 1-1s are for me to listen, learn, discuss, and then for the information to be disseminated. Nobody is more or less important or interesting or loved by me than anyone else. I currently have a weekly 1-1 with a couple people. I can't practically have regular 1-1s with everyone on the team because (1) that isn't scalable (2) it will take away from the priorities I've set above, but the following are the changes I'd like to institute:
Any 1-1s will be 1 hour blocks & and no more frequently than bi-weekly
I sit next to our head of marketing, physically, and take that for granted. We never have any 1-1s. I will schedule bi-weekly 1hr 1-1s with him.
If anyone thinks we should have or wants to have scheduled 1-1s with me please DM me and we can talk through it at get something regular on the books, perhaps monthly or quarterly.
I am opening up my schedule so that I can be more readily available for a call or video chat at a moment’s notice instead of being late to, missing and rescheduling calls. I will have an open door policy (as well as some closed door times).
Scheduled Meetings
I will be optional on all regularly scheduled meetings. They should all run well, responsibly and efficiently without me. Further, teams will evaluate (1) what meetings we should drop all-together and why and; (2) where and with whom they should be having bi-weekly 1-1s. A regular cadence to meetings is part of the foundation of our culture, yet we need to remain selective so we have good flow to our work and productivity.
Leadership Meetings
Our going-forward leadership meeting agenda will be something like this:
What are our priorities right now?
Can't be more than 3. Less is more.What are each team's priorities?
Can't be more than 3. Less is more.Do they align with our quarterly and annual priorities?
Can't be more than 3. Less is more.What meetings, priorities, tasks, and things should we stop working on?*
*Right now we horde priorities and tasks. An example that comes to mind is that in my house if we buy my daughter a toy, we give away and old one. If my wife buys a new pair of shoes, she donates an older pair to charity. The same should go for our tasks and priorities. If we are putting something new on top, something else has to come out (lmk if you find a charity that is looking for and accepting our tasks as donations). A team with too many priorities has no priorities. This is a shortcoming our organization has which has been manifested by my personality. I want to do everything but I can't, and neither can we. Let's get that laser focus.
Calendar
I will book 2 hour blocks for thinking and working on specific high-impact opportunities. Regularly throughout the week.
In conclusion, I work for you, for the company, and for our investors. Everyone should have the best return on my time and I hope that this points it in a better direction. I love being involved in every intricate piece of the business and with everybody at the most intimate level possible. This love, coupled with some of my compulsions listed above, are also creating a bottleneck for the organization. Let's get me out of your way as a headwind and make me a tailwind. We can re-evaluate after 90 days.