1st-time CEO learnings (vol. 2)

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


Volume 2 of 3

1. This is War

2. Compromising as your craft

3. Take Care of Yourself

Volume 1 (in case you missed it)

1. This is War

Please bear with my hyperboles here, this is fucking war soldier!!! Approach it as such. Let’s see what you’re up against.

Your Problem — The Objective

Identify a problem, the existence of which you find to be so fucked up that you simply can’t stop yourself from acting. Inaction would be unconscionable. You’re bringing it up in every conversation, subjecting yourself to its awfulness, starving to connect with the people it’s preying upon to go deeper with it, and imagining/preaching/creating a world where nobody has to feel the pain it causes.

This is the level of irrational enthusiasm you need to have for your problem because that is what will catapult you out of bed every day to sustain your assault to ensure its demise and your business’ success.

Do not

Do yourself (or those you convince to join you) the disservice of solving a problem you’re only ho-hum about. I fell into this bucket, and, believe me, it’s an easy one to drown in. You have to keep pumping yourself up to stay afloat, which is no way to prosper. I want you to be standing on top of tables, screaming at people, over the top maniacal about the problem you’re solving. That level of crazy is infectious, intriguing and a mother to beat down (and you will get severely beat down along the way). Your problem, that leach of all that is good, is what keeps you getting up.

Here are some questions to run your problem through:

  1. What are the negative consequences of its existence?
  2. Who specifically is impacted by them?
  3. How big of a deal is it for those victims? How are they currently coping Are they screaming out for mercy or resolved to apathy?
  4. What does a problem-solved world look like? How much better is it in measurable terms?
  5. Are you creating a problem to fulfill a solution you want to create?
  6. How is your problem currently being addressed and by whom? Why is that not sufficient?

Your Market — The Arena

Know what market(s) you are participating in and all that it encompasses — the history, the players, the biggest challenges (your opportunities), the pecking order, the alliances, who’s sued who, how business gets done, give me some more…

I do not subscribe that you have to be in a market where you have domain expertise. It can certainly be beneficial and radically reduce your barriers to success, but being a wide-eyed noob can bring its own benefits. As a market noob (new entrant), you are starting in the basement and have a shitload to learn. It’s your responsibility to become a domain expert by throwing yourself in full-bore.

Study. Question. Participate. Connect. Impact. Evolve. If you felt your market were fine just the way it is, you likely wouldn’t be there in the first place. So, remember, you’re here to shake shit up!

Your Customers — The Citizens

The tribal elders, the women and children, the taxpayers — your customers are your key constituency. You must listen to them, you must serve and protect them and you must get paid by them.

They are the court of public opinion. Without them, you are nothing. They are bigger and stronger than you, but they are a victim of your problem. You, yes YOU, have taken the reins to be their savior. Act like it!

You must balance leading and following them. Be a benevolent and inspiring force for good in their life and recognize that, without them, your tour is up.

Your Competition — Propaganda

Competitors are mere distractions in your arena and by focusing on them, you only make them stronger. Be up to speed, aware and vigilant of the competition and the noise they’re spreading in your market. Collect intel on them, liaise with them and see how you can use them to your advantage, but do not obsess over them.

Remember, the problem is your ultimate objective. Maintain laser focus on eliminating it while being a hero for your customers. That is how you will shut down your competition.

2. Compromising as Your Craft

Obvious: you have to make compromises in business to manage your resources, your bandwidth, your priorities, your sanity. As a startup CEO, you are often resource-constrained across the board — human, financial, time. You need to be able to reach compromises to make the most of your limited resources. You also need to coach your team in the craft of compromising, on both an individual and aggregate basis (across roles and teams).

Be Methodical

At different stages, you will have to make the tough compromises regarding your team (human resources), product (IP), finances (lifeline) and time (planning vs. executing). Careful, efficient consideration and cost-benefit analysis are required before you select a compromise. This is not a zero-sum game and there is no arbitrage, so understand and articulate the trade-offs (sacrifices) you are making and have conviction in your decisions.

Team

I have to admit I didn’t fully buy in to the importance of team before running my own company. That now sounds ridiculous to me, but at one point, I questioned the need of Co-founders and top talent. I figured I could muscle through on my own. I figured everyone was coachable. I figured wrong. There is no such thing as a minimum viable team.

Let’s start with your founding team. Dev, design, sales | hustler & hacker | mouse-trap builder, biz ops, go-to-market. These are roles you need to have covered on your founding team in some combination, which vary dependent upon what kind of business you’re in. What doesn’t vary is the need to contemplate and construct an aligned founding team.

Noam Wasserman of Harvard Business School has been studying Founders for 15 years now. He got on this beat by questioning why companies with seemingly unfair advantages fail. They may have a kick-ass product in a big-ass market with a smart-ass team, yet things didn’t go as planned. Money was burned, products were sunsetted and companies shut down.

What gives? Noam has found that 2/3rd of these failures are directly attributable to broken team dynamics. Guess what — these dynamics are in your control and the onus is on you to consider them before and during the life of your business. Noam has put together a survey here, which goes beyond just building your team into what kind of company you are really out to build (and why).

Positively, he’s found that this failure can be mitigated by doing your work up-front by having the hard conversations and making the compromises that might contribute to setting your company up for success.

Beyond the founding team, you need to construct and execute a hiring plan that takes into account what you’re trying to accomplish, when, where the holes are in your team and what resources you have (or need to acquire) to execute your hiring plan.

“Hire Fast, Fire Faster.”

I’ve been stung by both sides of this mantra by doing one and not doing the other. Be careful with hiring fast. Don’t be pushed into adding resources you’re not comfortable with and do not hire out of fear “shit, we need a [fill in position]. I’ll take anyone”. Strive to develop a hiring process that fits for the culture you’re creating.

Do fire fast. Give resources the opportunity to improve. Communicate with them what improvement looks like. If they are not improving, cut the cord. It’s best for all parties involved. In an early-stage startup, I believe it’s important to acquire team members that have been in the early-stage startup game before.

Product

MVP is real. It’s how you productize an idea and get it in potential customers’ hands in a tangible form, maybe even one they’ll pay for, as efficiently as possible. Avoid bloat and hemming and hawing. Set a narrow scope and execute on it. This is where compromising on features and communication (and embracing) of the shitiness of this version of the product are crucial. You and your team must be comfortable with what you’re putting out and must explain to everyone outside the company why A-Z aren’t going into the product right now.

Don’t get stuck with it View your MVP solely as a learning platform, not a milestone, and work your ass off to move beyond it as quickly as possible to the next iteration, again using a narrow scope of improvement (you may even end up releasing a slimmed down product). The communication and compromises between sales and product within your organization are crucial here. Sales wants more from the product. Product/engineering wants less (generally). You must get them to meet in the middle to keep moving the ball forward. Keep doing this!

Financial Resources

The cash you have in your bank is a finite resource. You are merely a custodian of this resource, and you have a fiduciary duty to manage it with care. Summon your inner miser and always be pushing to do more with less.

I personally hate it when someone’s gut reaction is to throw money at a problem. To me, it’s lazy and symptomatic of big-company thinking, where the coffers are open. This is where resourcefulness comes into play, and you do the hard work to scrap out progress. For example, don’t blow $20k on stock legal docs. Write your own and/or tweak existing and have your attorney review them. It will take more of your time, but in my book, that’s worth the savings.

However, sometimes it does make sense to spend money to acquire other resources — people aren’t free, repeat with me, people aren’t free and distribution (getting customers) is often not free. If you need more manpower, budget for it. If you have a compelling ROI for acquiring and converting users, pay for them rather than expecting them to just show up.

Time

What is the most important thing you can be working on right now? Are you working on that thing or attacking less meaningful tasks because they’re less intimidating or sitting on your never-ending to do list?

The compromise here is learning to say “NO” to yourself and to others. Seriously, start saying “no”. Don’t go to that meetup. Don’t take that meeting. Instead, focus on your most important thing and see it through to completion. I definitely struggled with this in my last company and am certain I will continue to struggle with it going forward. The first step is having the self-awareness to admit you struggle with managing your time/priorities followed by developing having the self-discipline to focus.

It is paramount to utilize this framework for GSD while remaining nimble with your priorities. Do not downplay the importance of strategizing and do not overdo it to the point of not executing on your plans. There is a balance to be found here, and you have to bake it into your and your company’s DNA.

3. Take Care of Yourself

Whatever works for you…

Take it from a workaholic who is striving for work-life balance. Your business is very, very important, and it demands just about all of you. And you probably demand too much from yourself most of the time.

That said, your business is not your life. Bottom line, it’s not. It’s not why people love you or why they’re friends with you or why you’re interesting or a good person. It’s just one thing you do, which happens to take up more of your time and energy than anything else.

It can only give you so much. You have to give yourself the rest. I will not wax on here. But prioritize exercise, disconnecting, dedicated time with the people that care about you (and who miss you, not your company, well yes your company, but hell you know what I’m getting at).

Lastly, HAVE SEX. Don’t let that slip. How you want to accomplish that, I’ll leave up to you. I’m in a committed relationship, so I have some latent demand if I can ramp the supply. However, I do need to be intentional about being around to provide the supply.

Be intentional about making these things happen and having a life outside of your business. Your business is a means to an end for what you want to accomplish in life.

That’s it for volume 2. I’ll be posting volume 3 in the next day or two. I’ve got the whole shebang in one long-ass post on my blog if you want to take down the whole thing in one sitting.