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!

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.

As entrepreneurs, we all have a story to tell that often includes disparate and seemingly unconnected experiences that lead us to the point where we could start our next companies. Rarely do I see a story told as well as Xiao Wang (founder and CEO of Boundless, a PSL company) does here in his recent commencement speech at UW. Enjoy and be inspired!

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.

“What details should we use for the final closing documents” is something that every entrepreneur wants to hear. I’d been working on a new idea for over 6 months, had a great team lined up and was on the eve of closing a $1.5M seed round with some of the best investors in the world including Brad Feld (Foundry Group) and a small collection of amazing angels. And then I killed the idea. Below is the note I sent to my would-be investors.

I take my responsibility as a CEO very seriously and would only accept your capital when I had a damn good, defensible plan on the best ways to spend it to achieve success and at this point, I do not. After careful consideration, the original idea of our “personal health record (PHR)” has too many issues/risks for me to proceed with the adequate levels of confidence. Therefore, I am postponing fundraising until I have more clarity and conviction around an idea worth funding. I spoke with Brad Feld yesterday and he was predictably thoughtful and supportive, which is how I have come to know him and the main reason why I want to work with him (and Foundry) in the future.

I’m happy to connect with anyone who wants to discuss in more detail, but the combination of incentives (most providers don’t want you/us to have the data and will therefore actively make it hard to get), patient apathy (most people  aren’t proactive and data-driven about their health), potential costs imposed by the provider during records collection (for example, in WA state a provider could charge a $22 clerical fee, $.96/page for the first 30 pages and $.73/page for all remaining pages (deal killer/frustrating/stupid) and this is implemented differently in every state and varies a ton), lack of a “I need that” feature, the significant amount of coding needed to do to get a viable solution and the fact that several competitors (Gliimpse, Prime, Picnic) have a significant lead on us, all total out to the wrong foundation to build around. Startups are hard enough without all of these factors stacked against you.

I hope you can appreciate the level of frustration and disappointment I feel right now. I am an optimist, pragmatist, and enthusiastic competitor and I fully expect to do a new company, hopefully in the healthcare space, and I hope you will consider investing in me (and my team) in the future.

Thanks again for your belief in me, the idea and the future of health.

Obviously, this decision and email are pretty hard to write. But, it was the right thing to do and the right time to do it. But, how did I get there, what could I have done to prevent this outcome and what do I plan to do differently as I look for an idea worth funding?

As a collegiate athlete (I went to Purdue on a swimming scholarship) and then a professional sailor doing long, offshore events, I’ve always dreamed about systems that could collect data about me, learn and suggest ways to optimize my performance. Then my mother was diagnosed with colon cancer, my father had a stroke and my brother and I struggled to help them understand their conditions, coordinate their care and look for the best solutions (specialists, clinical trials…). This was frustrating, time-consuming and not very “smart” and it seemed like a software solution could really help in both cases, a “platform for personalized health”. Ideas percolated for several years, while I built and sold Gist (where Brad was an investor) and started Rival IQ. At some point along the way, Brad asked me, “what’s standing in the way of you building the health platform and doing it with us as investors?” I didn’t have a good answer, so I got to work.

My first steps were a blend of customer development and MVP creation. I set up this survey to learn about potential customers (would be great to have your input too) and started having conversations with users in my target personas (“self-advocates” — people with critical or chronic health conditions looking to take control of their own health and “optimizers” – people who wanted to use data and experimentation to get more from their bodies and minds). I was lucky as I have experienced both of these states so I was scratching my own itch, which is a good thing to do as an entrepreneur. Then, as I’ve done in the past, I got together a team of “night-time hackers” to build a rough MVP of our core idea. This team met on Wednesday nights and included 3 developers, 1 designer and me. All of us were interested in the problem space, working with each other and brought complimentary skills. We grabbed hours when we could on evenings, nights and weekends and focused our sessions on learning, data sharing and trying to get something working. The goal was to make a mobile app that worked something like; install, find your doctor, take a photo of your drivers license, “sign” on the phone (to validate identity) and then magically (after a few days time) you have copies of all your past health records, accessible on your phone. Obviously, we had many ideas of what you could do next (visualize your health history, find correlations and causation, compare with norms, share with others, enhance with other data…) but we wanted to make it fast, easy and free to get your records. After a few months, we had this working (with lots of issues) and it was really cool!

Starting a company requires some blend of imperfect data, reasonable assumptions and a collection of smart people who think the problem can be solved, but is ultimately some leap of faith. With a bunch of customer input, tons of research and an MVP, I decided to quit my day job and go for it. I went back to Brad, further articulated my plans, solutions to some of the issues we found, built a rough model with users, growth, team, revenue…and decided I needed 1.5M to get going at the pace I think the idea deserved. Brad was thoughtful in his questions and we agreed to fund the new company. I was on cloud nine and it was hard to contain my excitement!

I’m a big believer in creating a “big tent” of smart people who can help an idea succeed and while Brad was happy to take the whole 1.5M, I wanted room for angels who could help the company grow and/or add unique value. We agreed to carve out 250K, for up to 10 angels (@25K each) in the round. I articulated that I wanted 2-3 people in 4 categories;

• Quantified-self geeks – people who used data to gain an advantage, often in sports
• Medical disruptors – had experience changing the healthcare space with software, data and a focus on the patient/consumer
• Platform innovators – companies that aggregate data and provide new value and/or had similarities to our approach around personal storage (e.g. Mint.com, Tripit.com, Dropbox, Evernote)
• Company builders – CEOs who could help me be better, grow a big company…there is always more to learn

For each category, I made a list of my top prospects. With Brad’s support as a foundation, I leveraged my network, found connections and followed much of the advice I’ve given before in these posts. For each investor, I articulated the vision, our progress and why I wanted them specifically to be part of the company. Within 30 days, I had an awesome group lined up with several people I only dreamed of getting when I started the process. Time marched forward, we hired an awesome legal team with great experience in the space, drafted documents to form the company, raise the round and get started. I made my first offer to a full-time employee, who could add necessary medical expertise to the team. She chose us over an existing offer and gave notice to her current employer. I started talking about the idea more broadly and made plans for an impending public disclosure around the financing. All systems go with a plan to close in mid-October!

While I was raising the money, we were also working on enhancing the prototype, diving deep into policies and regulations, talking to medical providers and continuing our customer research. As my enthusiasm for working with the team and the investors was increasing, we starting finding serious structural issues in the overall business, mostly outlined in my note to investors. We looked hard at incentives (who wanted us to succeed and who might want us to fail) and I will do this much more deeply in the future. We considered many, many options on ways to incentivize the consumer more and solve the structural issues that seemed entrenched on the provider side (very hard to do). I was optimistic that we could find good solutions but as the days marched forward toward the financing timeline I had communicated, the negatives mounted and my confidence decreased.

During every startup, you reach points of critical inflection; when to narrow to a specific focus (vs. idle chit-chat about ideas), when to start coding an MVP, when to commit full-time and quit your day job, when to raise money, hire your first employees… Obviously, there are many more points in the future, but these early points are some of the most critical. As an entrepreneur, each of these points presents an opportunity to take stock, weigh the risks/rewards, make a plan and then re-commit to the next major milestone/inflection point. Knowing Foundry and the investors I’d lined up and the team I’d recruited, I knew that we were all committing to at least 3-10 years of our lives to work on this idea. I wrestled with the idea, brainstormed with the team, talked with other CEO’s I respected and discussed with my wife who has seen me succeed and fail in the past. The process of discussion and communicating my decision-making criteria helped it crystallize my opinions and in the end, the calculus was not right.

I was in Boulder for a Full Contact board meeting and I’d aligned our schedule around this date. It was planned to be a celebration of the financing, a new company, and a new adventure. Brad and I first met during a run along the river in Denver way back in 2008. While building Gist, we talked about many challenging issues while running or walking. On this day, we walked to Boulder creek trail and I explained my logic and decision. He seemed to know this was coming, which is likely just good investor intuition. I was sad, frustrated and even a little embarrassed. He was conciliatory, thoughtful and supportive. The next day, I sent my note to the other investors and the other partners at Foundry. Some were surprised, many appreciative and this made me feel even better about my decision.

I remain sad, frustrated by the systems and incentives at play in healthcare.   As for healthcare innovation, I do plan to keep working toward an idea worth funding. I hope the other players in the space succeed and I am inspired by people like Eric Topol, Jonathan Bush, Peter Diamandis, and Atul Gawande to find solutions that deliver better results and a life of “optimal health and peak performance”.