1st-time CEO learnings (vol. 3)

a 3 part series detailing what I’ve learned as a 1st-timer


Volume 3 of 3

1. Do Shit that Matters

2. Define Success

3. Manage Like a Boss

Vol. 1 | Vol. 2

1. Do Shit that Matters

Macro

Shit that matters to you personally, to society at large, to a grouping of people/orgs. (your market, your contributors). Your vision must matter and must resonate across all of these, and it starts with you.

Be thoughtful here and generate answers for yourself. These answers are for you first and foremost. So, ask yourself what matters to you. Then ask why. Then prioritize them and select one to focus on solving. Then ask yourself how far you’re willing to go for it? Once you have your answers, get started doing something that matters. Note: this thought process is not time wasted. Better to know what matters to you out of the gates rather than 18 months down the road…

You do not found a startup to do something marginally better. You may start a small business or side business to do so. In a startup, you are out to disrupt and be massively/radically (1ox) better than what exists today. You exist to be big, bold, exciting, crazy and inspiring.

So, how much does what you’re doing with your business really matter to you? Are you attacking a BFP (big fucking problem), the mere existence of which you consider to be abhorrent?

Micro

Determine and do shit that matters to your business. This is how you execute daily, weekly, quarterly, annually, up until you are no longer running this business.

  1. Focus — Create strategic plans with goals and tactical action items so you can move the ball toward making your vision reality. Don’t waste your time with fake progress; don’t make up work because it feels good. Do the important things, the hard things, the things that matter.
  2. Accountability — You need to hold yourself and your team accountable so you don’t get sidetracked. You do not have the luxury of wasting time. Set and communicate goals. Work toward milestones along the way. Demand that others hold you accountable and don’t let you slip.
  3. Progress — Maintain an eye on and measure progress. Demand it. Celebrate it. Crave it. You and your team need measurable results that don’t lie.

2. Define Success

For Yourself

You control what kind of life you lead. Of course, external forces affect your course, but you control the roadmap. Relish that fact and expend the mental cycles required to chart your course. Do not let others define your life and what constitutes success for you. Find like-minded people that share your values and definition of success and connect with them to live a successful life, whatever that is for you.

For me, I know I want to have a meaningful impact much larger than myself. I’m good at connecting people and encouraging others in their pursuits, and I am energized by new experiences (much more so than new things). Success for me includes serving as a catalyst for others to fulfill their visions, including my family, my future family, those in my network, and just about anyone else I run across who is hustling to make things happen. For me, success is being instrumental in others’ success.

One exercise here is writing your obituary.

For Your Business

Defining success for your business before you start it gives you another decision-making filter for all the aspects of that business and the compromises you have to make along the way. It, along with your vision, constitute your North Star.

As I said earlier when I told you to take care of yourself, your business is not your life. It’s one piece, and it’s on you to fit it into the overall picture of the life you’re painting. If, for you, selling a company for $1 billion constitutes success, that’s all good! So, assuming that’s your measure of success, take the steps to create a company where that can be a realistic outcome.

That very well could mean running a smaller business as a first step if you’re focused on the outcome of selling that business and achieving a positive ROI for your investors to position yourself into a VC-fundable CEO for your big thing. That’s only one course. There are many others you can take, but there is only one measure of success. You should view it as if you don’t achieve that, you have failed, which is also just fine. It just means, you’ll probably be at it again with more learnings to build your $1 billion business.

3. Manage Like a Boss

You are the CEO, which means you are the boss of everyone involved in helping you build your business (team, advisors/mentors, investors). You have to manage up and down your support system, which involves a mix of:

Communicating

Strive to be an excellent communicator. You do not have to be a guru of interpersonal relationships; you do have to communicate with confidence and purpose. This entails being proactive, establishing a cadence, knowing your audience, being a good listener, being an engaging storyteller (this can come in many forms) and getting to the meat of/not clouding issues.

As you can probably realize from this post, I tend to over-communicate, which is both good and bad. I like to make sure everyone on my team has a clear picture of what’s going on and why we’re doing what we’re doing at any given point. I want my team members to be empowered, invigorated and accountable with clarity as to how I expect them to add value. I value transparency, but I have learned I must, at times, temper my gut reaction to overshare, as it can be counterproductive and even damaging.

We all know startups are hard but, as CEO, you must paint a positive picture for your business. Share your struggles for the purpose of getting help with solving them and always bring a solution to the table. Being overly negative (or even realistic) can be demoralizing for your team and sow doubt in the minds of your investors/advisors. So, be real with yourself and your team

Delegating

Delegation starts with trust. It’s the only way you can cede control of the reins and focus on the most important thing you can be doing at any given time. You cannot do it all forever. You are not the best at everything. You must rely on your team to GSD. Provide instruction, motivation, support, and get out of the way. Understanding what makes your team members tick, what gets them into a flow state, is very valuable here.

Pissing people off

As CEO, you have to have the hard conversations and make the unpopular decisions. So, put on your big boy pants, be diplomatic and act decisively knowing that you are only doing what you believe to be the best courses of action for your business. Then, have a beer with your team or go do some yoga and don’t beat yourself up.

That’s it for this series. You can visit my blog to check out my other writing and connect with me. Thanks for reading! -BP