Startups move fast and if you’re doing it right, you make a ton of progress on everything from customers, product, team, systems, press…very quickly and it’s easy to lose track. And, since most leaders are very focused on the future and what’s next, they forget to celebrate the “wins” or look back at what’s been accomplished. But, when they want to make the documentary about your startups’ massive success, like they did for Apple, Pixar or General Magic (well they didn’t have commercial success), or you want to be featured on an Acqired.fm podcast  (produced by my partner Ben GIlbert) like Alibaba or Epic Games, they’ll need material, so I suggest you develop systems to create, accumulate and celebrate the “memories”.  

Here we are; my brother Rob, Adam Loving and myself when we started HelpShare. It’s fun to look back but I wish I had lots more photos or collections from those early days.

Early versions of websites are cool and often embarrassing at the same time. Here is HelpShare (in 2000, with cringy “smoke” background) or Gist, (circa 2008) which still holds up…from the awesome Internet Archive aka “the Wayback Machine.” 

One way to do this is a Slack channel, which seems to be the best as everyone can post, share and see the history from a variety of different inputs (screenshots, photos, videos, other applications…) Evernote works too or some kind of shared folder (Gdrive/Dropbox) but not as much fun to scroll. I suggest you put in more vs. less in the “history/memories channel” as you can always delete later but it’s really hard to recreate the moments and so easy to forget the details.  

Really think hard about all the little wins. The first customer, the release of a key feature, hiring your first X kind of role, your first product spec, company values…it all matters. Take screenshots of the time your product first fell over due to customer load or the Zoom birthday serenade. I am pretty sure you’ll forget who was actually there and what the product looked like when you made your first 1K, 10K, 100K, 1M.

The ZeroCard has lots of photos of their team out and about with Zero gear on. Here’s one of me, in the Enchantments sporting the hat.  And here’s one during my first trip to Tulsa and collecting a cool beer koozie (nice schwag).

In pre-covid times, Remarkably had Friday happy hours where different people “host” and were in charge of the food and drinks and they have lots of those in the memory channel. Scott Dorsey, the founder of ExactTarget and now managing director at HighAlpha, used to do a “friday note” which is another form of history/memories. And a recent tweet from Paul Grahm about the early days of Stripe.

Our PSL company TeamSense just celebrated our 1000th end user so we have that marked…just good (and sometimes the bad) of how the company evolves. Their team recently implemented a hat for some zoom fun!

While nobody has done this yet, I am encouraging our CEOs to consider a “yearbook” for everyone in the company. This could be a fun video time capsule or a photo-book, presented to everyone who was there for the year.  Imagine 10 years later or at the IPO, a stack of the photo books on a shelf and thinking “Remember when…”

To all the memories of all the startups!

Starting a company is hard. The variables of selecting the best idea, finding co-founder(s), unknown duration of customer discovery, product/market timing, and financing strategy/timing makes it even harder. And, starting a company takes skills, functional practice, and a little luck. In my experience, a good way to get started in all of these areas is by doing a “side project.” I’ve done this many times with success including Rival IQ, my most fruitful side project to date.

Firstly and perhaps most importantly, keep your day job while you work side projects. Sure, one of them might turn into a company at which point, you can focus on it full-time, but wait until that is absolutely necessary. This gives you infinite financial runway and will force you into doing the most important things in your limited off-hours. This will be true for your other co-conspirators too. And, while you might not think you have the time, you and your founding team should get used to working on nights, weekends, and lunch breaks to get everything done. It’s just another part of the “startup training” regimen.

If you are functioning as the “CEO” (read more about the 5 jobs of the CEO here) it’s your job to set out the basic vision for the project/idea and plan. It’s also your job to set up the conditions for your team to work together and succeed. Here is where some structure makes all the difference;

• Set the right expectations – doing side projects is more about hanging out with fun, interesting people, making things, and learning. Like playing in a band. Sometimes what you make finds a great audience and can deliver commercial success, but side projects should feel more like jam sessions vs. trying to be a successful rock band, at least when you start out.
• Outline the vision for what the offering should be. Using my simple CVFB method is a good way, but you can use Lean Startup or Business Model Canvas too, I just find them too “heavy” for a side project. Knowing what you want to build, for whom is pretty important and will help you make progress toward a real thing and audience. Be open to modification of the vision on a weekly basis. Read it and refine it and restate it, every week as you set and reset direction and activities. (this is another part of leadership and structure).  If you’ve picked right, there is usually limited modification and the same CVFB might last years, but when and how you perservere or pivot is important.
• Set time and commitment expectations from everyone – I like to suggest 3-5 hours/week for everyone on the team. This would include one hour of planning (what are we going to do for the week), 1-2 hours of working together/collaborating on key deliverables, and 1-2 hours of everyone’s personal time working on personal deliverables. If someone on the team has more time and wants to spend it on the project, make sure the others don’t feel guilty about their level of commitment or time. Five hours/week times multiple team members can make pretty massive progress.
• Develop a weekly working cadence – I suggest something like “we meet on Tuesday nights from 6-8, then we squeeze in the additional three hours when we can during the week.” You could set up a “check-in” on Friday as people are likely going to be doing work over the weekend and you want to show up on Tuesday with all the work completed so you can start again the following week.
• Give people an “out” – As you meet new people you want to bring onto the team, encourage them to just commit for one month or four “sprint weeks.” And, at the end of the month, everyone can evaluate how it’s going and if people aren’t having fun or learning, it’s totally fine to “break up” or leave the project with no hard feelings. This monthly cadence will also allow the team to reset a vision, what they might want to achieve given the team they have, and how well the project is progressing. There are many reasons why people might want to leave; they don’t like the team, they don’t like the direction of the project, they don’t have the relevant skills needed, they can’t manage the time commitment…but as the leader/CEO, you need to make it easy for people to join and to leave without stressing them or the rest of the team. Remember this is a side project.
• Know when to quit/pivot/restart – most ideas don’t work, usually due to customer demand — you just can’t find a set of early adopter customers who really want your thing and are willing to pay for it in the way or amount you imagined. You need to spend enough time trying to find out. Who knows how much time this might require, so the monthly cadence of “what are we doing, why, for whom…(CVFB) and the personal team commitment (are we having fun hanging out, doing this work and do we want to continue) is a good forcing function. Sometimes teams disband, sometimes they kill one idea and start working on another, which might mean some members of the team want to leave…all of this is good learning and good to reflect on during the first meeting of the month.

I give this advice to lots of people and a few years back, I gave a talk to a bunch of entrepreneurially-minded students at Purdue’s Anvil (the hub of entrpreneruship) with similar recommendations. I recently connected with my friend Akash Raju, who led many of the entrepreneurial efforts at Purdue and has used this approach to launch his new company, Glimpse which made it into and just completed YCombinator. It worked for him and it’s worked for others too!

For me, Rival IQ was a side project that turned into a successful, venture-funded company. How to Live to 200, our podcast about health, longevity and human performance started as a side project, we recorded a bunch of episodes and then “paused” mode when we all got too busy. PersonalScience is another one, in this case, we had many people come in and out and I left the project when I joined PSL, and Richard and the remaining team continue to drive this forward. Prepared, “a better way to prepare for your business meetings” is a side project for me that I am still dabbling with so feel free to sign up, test it out and give me feedback. Each of these gave me a chance to hang out with smart, motivated people I wanted to spend more time with, in a low stakes kind of way. We learned new things, we learned about each other and we made some cool products. Give it a try yourself.

PS – if you’re a rockstar software developer or product designer and want to consider a side project with me, I have lots of other ideas! Send me an email – tam@helpshare.com

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.

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!