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The 5 jobs of a startup CEO

With my work at PSL in starting new companies, being on boards and in my own experiences, the CEO of a startup has 5 jobs;

– Set and communicate a clear, compelling, and consistent vision – this comes in the form of presentations, team meetings, town halls, 1:1s, board meetings, investor pitches, customers calls…  It’s a blend of the big picture— “how will the world be a better place when we succeed” as well as “where does your work or contribution fit in.” This requires the repetition of the same messages and methodical re-examining and modification of direction and priorities. If the messages change dramatically, it requires an increased frequency of the new message. In my experience, using different time horizons to reflect and re-examine are useful; tied to product sprints (every 2 weeks), monthly investor updates, quarterly team strategy reviews, semi-annual budgeting cycles, and fundraising roadshows every 12-18 months.

– Hire and manage a great team – this seems obvious, but many CEOs don’t plan or budget enough time here. Management is helping each individual understand their role, responsibilities, and metrics as well as aligning those to people’s skills, gaps, and areas of learning. It’s about solving interpersonal issues between team members. And, as the strategy changes or the business outstrips someone’s skills or interests, it’s about making hard choices and changes and then re-aligning again and again and again. Being clear about “proactive/active” and “opportunistic/passive” hiring; “who do I need now and what’s my plan/process to get them”…and “whoa, this person is amazing, how do I find them a spot…”

– Find the resources for the team to do their best work—the team needs salaries, beer/pizza/great coffee, fast computers and big monitors (one form of resources)…and that takes money (another resource). The CEO needs to find and organize these resources. This is usually thought of as fundraising, which is critical. Your job as CEO, is to raise the necessary capital, full stop! This is usually from investors, so plan your fundraising strategy wisely.  But you can also get capital from customers, and you are also the first and best salesperson. Coincidently, the more customers you can close, the easier it is to raise investment capital, but you need to make sure the team can stay focused on doing their best and most aligned work, without distraction or worrying about making rent.

– Improve the process in the way work gets done—a startup is a machine and you need to be a mechanic. Look inward toward “systems and tools” to make the team work better, smarter, faster. As recommended for the cadence of communication (every 2 weeks, monthly, quarterly…), consider a similar cadence for making improvements on the process. This might be the way you’re organized, how you communicate, what software you use to support a specific function, who runs a specific meeting, who attends which meetings, how you engage with customers or investors…or all of these things.

– Discovery and focus on “make” or “break” parts of the business – in every company and about every quarter, there are major things that could kill the business if they fail and others that could create a step-function improvement. This is oftentimes fundraising, which will need to be a focal point during specific quarters but could also be a specific customer win, channel partnership, conference appearance, or key hire. It could also be an internal process, sub-system or team challenge. As a CEO, if you put one or two of these on your goals every quarter and put the requisite time and attention toward it as only a CEO can do, it will increase your likelihood of success.

Being a CEO is a hard job and it takes consistent focus on the business and yourself. Though the day to day work should be largely filled with these activities, it is also important to find time to learn, rest, grow, recover, and live. That’s job #6.

The Playbook – what the water (oceans and pools) taught me about entrepreneurship

Last week I was the featured guest on The Playbook, a series put on by Geekwire focusing on athletes turned entrepreneurs and the lessons they draw from sports. John Cook did a bunch of research about my swimming and sailing past and even dug up some dirt from my brother (we founded 2 companies together). It was a fun and personal conversation that gets at a lot of my past, present and even some future.

A good summary of the event is here — https://www.geekwire.com/2019/save-rupert-murdochs-finger-startup-lessons-entrepreneur-t-mccann/

Video of the whole session is here — https://youtu.be/e_7_kCuU4MI

And, we were lucky enough to have Guillaume Waitr there to do real-time sketching of the event and my key points.

Thanks to John Cook and the whole Geekwire crew for having me at the event and all you do to help the PNW ecosystem thrive!

A new podcast for entrepreneurs…

I’m a huge fan of Techstars. Brad Feld was one of my investors in Gist back in 2009, about the time that Techstars was getting off the ground and David Cohen and the Techstars fund is an investor in Rival IQ. I’ve mentored Techstars teams in Boulder, New York, LA and on every program we’ve had in Seattle since 2009. It’s been amazing to see their growth and impact they’ve had on the whole startup ecosystem.

So, I was honored when they wanted me to be one of the early guests on the Give First Podcast. It’s awesome to see them sharing even more knowledge and lessons learned from founders with the community. I hope you enjoy and share too.

Important things I’m not doing, yet (ITINDY)

When you talk to experienced investors and founders of startups, they tell you it’s all about “focus”, but how do you make that actionable and structured? As the business changes and evolves, a founder (you) will also get lots of ideas (some good, some bad) from your team, customers, investors, other companies…but how do you know when or if to act on these?

For me, I developed the ITINDY approach – which stands for “Important things I’m not doing, yet”. As the ideas with merit roll in, I add them to this list, acknowledging both their value (Important) and the fact that I am not losing my current focus to act on them (Randomizing) but I might in the future. Then, I set 2 types of milestones to review the list or specific items; one is “date based” like at the beginning of the quarter or June 1. The second type of milestone and the one we use most often is a “success metric” which could be achieved in the near future or never depending on how the business grows and how right our assumptions were. Examples would include revenue (X MRR), Y number of customers, a funding round > Z, the 10th new hire…all very specific and quantified. If you chose incorrectly on a market, pricing, a sales strategy…you might never achieve these metrics which is where the date-based milestone comes in, giving you an out to make major changes in strategy.

Often, as part of my strategic plan, I have these goals aligned, so they should happen around the same time assuming the business is growing as planned like; we should hit 50 customers, 25K MRR and our 10th hire around June 1. By setting this expectation for me, the team, my investors, even customers we all get into a good flow of the things that are “important now” and the things that might be important in the future and most importantly an expectation on when we’re going to discuss and decide about doing or leaving something on the list.  As we approach the date or success milestone, we also know it’s time to review, re-order the list and collect relevant data to make a decision, which drives a strategic planning session. FWIW, I usually do this in a Google Sheet where tab 1 is the high-level strategic plans and goals (months across the top, key priorities, and metrics down the side) and we keep ITINDY on a separate tab. As we reorder/group the list for strategic planning, it has a way of outlining who we need to hire next, what projects we want to fund (raise more money) or what major features to build.

I have used this method with really good success to keep the team aligned, working toward near-term goals, but with the expectation that we will keep evolving the business as a measured and methodical pace and avoid the proverbial “shiny penny” scenario. Stay focused and make your list!

P.S. – this will work for your personal life too.  For example, at some point I would like to teach at the college level, write a book, hike the TA trail in New Zealand, do a transatlantic crossing on a big multi-hull, land at Nairobi airport…and the list goes on.