My friend George, one of our co-founders at Return Path (according to him, the best looking of the three), has a wonderful and simple framing question for thinking about product strategy:  what job is your customer hiring you to do?  No matter what I’m working on, I am finding George’s wisdom as relevant as ever, maybe even more so since I am still learning the new context.

Why is this a useful question to ask?  It seems really simple – maybe even too simple to drive strategy, doesn’t it?

It’s very easy in technology and content businesses (maybe other spaces too) to get caught up in a landslide of features and topics. In a dynamic world of competition and feature parity, product roadmaps can easily get cluttered. They can also get cluttered by product teams who have their own view of what should be the next feature, module, or content widget. Sometimes looking at product usage data is helpful, but sometimes it produces more noise than signal because it can easily miss the “why” or change day to day.

And once a product is mature, it can be very difficult to understand which of its many elements — even if they are all used — are the ones truly driving the most value for customers. It’s easy to assume it’s the newest, the slickest, the ones that are generating the most buzz. It’s even easier to assume that when it comes to content. But sometimes it’s now. Sometimes it’s the legacy part of the product. Sometimes it’s a small side feature you don’t focus on. Sometimes it’s something you used to do but don’t really do any more!

By asking customers the simple question — what are you hiring us to do for you? — you can start to get to the heart of the matter, the heart of what your strategy should be.  Peeling the onion once you understand that and getting into the specifics of the different tasks or jobs your customer does that derive from your main point of value, as George would say, “jobs to be done,” is much more straightforward. When defining a Job to Be Done:

• Focus on a functional job (not an emotional one, e.g, “I need to look smart to the boss”)
• Try to ensure that you are looking at the whole job, not just a piece of the job. It’s easy to get too narrow in your definition
• Make sure it is the customer’s definition of the job, not yours

There’s always a role and a need for innovative product owners to help define a space, define value, demonstrate it for customers.  This framework is meant to be additive to a high functioning product owner’s job, it can never replace it.

(As a small post-script, Friday December 6 marks 20 years since we started Return Path…a fitting day to post a bit of a tribute to George!)

(This is the second post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Introductory post is here.)

Tuesday, March 17, Day 1

• Extended stay hotel does not have a gym.  Hopefully there is one at work
• Walking into office for the first time.  We are in a government building in a random town just south of Denver that houses the State Emergency Operations Center (SEOC) and the Department of Homeland Security and Emergency Management.  These are the teams who are on point for emergency response in Colorado when there is any kind of fire, flood, cyberattack, or other emergency
• 
• 
• MAJOR Imposter Syndrome – I don’t know anything about anything
• 7:45 meeting with Stan
• 8:15 department briefing
• Met two deputies – Kacey Wulff and Kyle Brown.  Both seem awesome. On loan from governor’s health care office and insurance department
• Team “get to know you” was 4 minutes long.  So different than calm normal 
• Emergency Operations Center in Department of Public Health
• Small open room with over 100 people in it and everyone freaking out about not following best practices – no social distancing
• 
• Leader giving remote guidelines
• Lots of “Sorry, who are you and why are you here?”
• Local ops leader Mike Willis excellent – calm, inspirational, critical messages around teamwork, self-management, check ego at the door (turns out he is a retired Brigadier General)
• HHS call – maxxed at 300 participants, people not getting through, leader had to ask people to volunteer to get off the line (oops)
• Lunch and snacks in mass quantities here – it’s not quite Google, but this part does feel very startup.  I wonder if the Emergency Ops Center does this all the time or just in a crisis. Guessing crisis only but still super nice.  Also guessing I will gain weight this week between this and all gyms in the state being closed down
• Lots of new people and acronyms
• Multiple agencies at multiple layers of government require a lot of coordination and leadership that’s not always there, but everyone was incredibly clear, effective, low ego.  A lot of overlap
• Got my official badge – fancy
• Jared calls – just spoke to Pence, his guy is going to call you – tell him what we need…”uh, ok, now all I have to do is figure out what we need!”
• Fog of War – this room is healthy and bustling and a little disconnected from what’s going on, no freak out
• Kacey and call from Lisa about Seattle being on “Critical Care” because they don’t have enough supplies, meaning they are prepared to let the sickest people die – oh shit, we can’t let that happen here (or is it too late?)
• Got oriented, sort of
• Slight orientation to broader command structure and team
• My charter and structure are a little fuzzy, guess that’s why I’m here to figure that out
• Late night working back at hotel.  Thinking I will become a power user of UberEats this week

Wednesday, March 18, Day 2

• Gym at work is closed along with all gyms everywhere.  Looks like a lot of hotel floor exercises are in order
• Ideas and efforts and volunteers coming in like mad and random from the private sector – no one to corral, some are good, some are duplicative, all are well intentioned.  Lots of “solve the problem 5 ways”
• Shelter in place?  Every day saves thousands of lives in the model – credibility with governor
• State-level work is so inefficient for global and national problems, but Trump said “every man for himself” basically when it comes to states
• Not feeling productive
• Productivity is in the eye of the beholder.  Kacey totally calmed me down. Said I am adding value in ways I don’t think about (not sure if she was just being nice!):
  • Connection to Governor really useful for crisis team
  • Basic management and leadership stuff good
  • Asking dumb questions
  • Out of the box thinking
  • Liaison to industry and understanding that ecosystem
  • Arms and legs
  • People used to working in teams on things – different expectations in general
• Ok, so maybe I am helping
• Colleague tells me about Drizly, the UberEats equivalent for alcohol delivery. Good discovery.

Thursday, March 19, Day 3

• Weird – my back feels better than it has in months.  Maybe it’s the pilates, but still, seems weird.  I wonder if the higher altitude helps. If so, we will be moving to Nepal. Have to remember to mention that to family later
• Governor Policy meeting 9 am – “Cuomo is killing it” – words matter – “shelter in place” and “extreme social distancing” debate
• “The models are wrong – so let’s average them”
• We need 10,000 ventilators. We have 700.  Uh oh.
• Raised issues around test types and team capacity…Gov expanded scope to include app and still pushing hard on test scaling.  Gov asked for proposal for expanded scope and staff by 4:30. Guess that’s the day today!
• Recruited Brad to lead Private Sector side of the IRT’s work. Important to have a great counterpart on that side. Glad he agreed to do it, even though he’s already vice chair of another state task force on Economic Recovery
• Senior Ops leader interrupts someone during daily briefing – quietly says to the whole room “not vetted, not integrated, not helpful” – incredible.  In the moment, in public which normally you don’t want to do but had no choice in this circumstance – 6 words gave actionable and gentle feedback. Great example of quiet leadership
• Private sector inbound – well intentioned and innovative but overwhelming and hard to figure out how to fit in with public sector (e.g., financing to spin up distributed manufacturing)
• Team huddled and created proposal for new name, structure, staffing, charter, rationale, etc.
• Present to senior EOC staff for vetting, feedback
• Feels like I’m adding value finally – plan creation and “bring stakeholders along for the ride” presentation/vetting AND getting the team to stop being hair on fire and focus on thinking and planning and staffing
• Present to Gov – “brilliant” – then after, Kyle says “I’ve worked for multiple governors and senators, and this is the first time I’ve heard something called brilliant” (not sure it was brilliant)
• Now to operationalize it, stand up a team, replace myself so I can get home once this is marching in the right direction at the right speed
• Transferable skills (leadership, comms, strategy, planning) – not just missing context here but missing triple context – healthcare, public sector, CO
• Day 3.  Feels like longer
• Still, feels like adding value now.  Whew.  
• Dinner with a Return Path friend who came down to my hotel’s breakfast room, picked up takeout on the way, and sat 6 feet apart. 

Stay tuned for more tomorrow…

(This is the first in a series of three posts on this topic.)

Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys.

All of us would benefit from having an Albus Dumbledore in our lives.  But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is. 

Why work with a Coach or a Mentor?  I’ll start this post with a quick argument in favor of CEO Coaches and Mentors (sometimes called Advisors).  Even as a 20-something first-time CEO years ago, I was deeply skeptical of the value of a Coach, but that was in 1999 or 2000 when coaches weren’t so commonplace.  Now that their value seems much more obvious, and there are so many amazing Mentors and Coaches available, I’m surprised by how many CEOs I speak to still seem skeptical about their value.  Just think — the world’s greatest athletes, the ones who get paid zillions of dollars because they are the best in the world at something, use MULTIPLE coaches DAILY to perfect their craft and keep them focused.  Why should Rafael Nadal or Serena Williams have a trainer and a coach, but not you?

I’ve benefited over the years from the advice of more people than I can ever count or thank.  But when it comes to being a CEO, I have leveraged the counsel of a CEO Coach or Mentor principally in three different areas:

1. Functional topics on the craft of being a CEO from the lofty “how to run a board meeting” to the nitty gritty details of “how to do a layoff”
2. Developmental/behavioral topics like “how I show up as a leader in the organization,” or “how to be a better listener”
3. Team Effectiveness topics like “how do I get the most out of my leadership team,” or “why doesn’t Person X trust Person Y and how does that impact team performance?”

In some unusual circumstances, you can find a person who does all three of these things for you and can scale as you and your company grow.  But for the most part, getting all three of these things requires engaging two different people, and maybe even more mentors.  

What’s the difference between a CEO Mentor and a CEO Coach?  Counsel on Item 1 above — what I would call CEO Mentorship — almost certainly requires someone to have been a CEO — preferably multiple times, or for a long period of time, or through multiple stages of company growth, or two or three of those qualifiers.  This is the kind of person who can literally teach you how to do CEO things.  These people are super busy, they won’t have open ended amounts of time for you, but you should expect sage wisdom and answers when you need them.  And you can have more than one of them at a time, or change them out as your company evolves and your needs change.

Counsel on items 2 and 3 — what I would call CEO Coaching — frequently come together in a professional who is and has been for a while, a coach.  The person might have had a significant career in business before becoming a coach but wasn’t necessarily a CEO.  The person probably has some kind of academic grounding, like a Master’s degree in Organizational Development or Industrial Psychology, or a Certificate in Coaching.  This is the kind of person who can do things for you and your team like facilitate meetings, run assessments like Myers-Briggs or DISC, and coach other leaders on your team.  This person is dedicated to helping you be the best leader, professional, and CEO that you can be and must be both empathetic and comfortable pushing you hard.  

Sometimes you get mentorship and coaching in the same person, but almost only with CEO Coaches who are also CEO Mentors by my definition above.

Five signs you need a CEO Mentor and/or Coach:

• You are playing ‘whack-a-mole’ — running from crisis to crisis in your organization and are not able to make time to think, be current with email, or make time for important things like hiring senior executives
• Your board is getting frustrated with you, your team and/or the lack of progress in the business
• The company isn’t scaling as fast as it should
• Your leadership team is not a cohesive team and you are in the middle of all decisions
• The company has high employee turnover and/or poor reviews on Glassdoor 

Do yourself and your company a favor and invest in a CEO Coach and Mentor(s). It’s an investment in accelerating your own and your company’s success. In later posts, I’ll talk about how to hire and best leverage both Coaches and Mentors. 

Next post in the series coming:  How to Select a CEO Mentor or CEO Coach

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post:

My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company.

Let me put it in starker terms:

Grow or Die.

Every executive, every professional, can scale further than they think is possible, and further than you think is possible. Most of us do have some ceiling somewhere…but it will take us years to find it (if we ever find it). The key to scaling is a growth mentality. You have to not just value development, you have to crave it, view it as essential, and prioritize it.

Startups are incredibly dynamic. You’re creating something out of nothing. Disrupting an industry. Revolutionizing something. Putting a dent in the universe. For a startup to succeed, it has to constantly put something in market, learn, calibrate, accelerate, maybe pivot, and most of all grow. How can a leader of a startup scale from one stage of life to the next without focusing on personal growth and development if the job changes from one quarter to the next?

I was lucky enough to have a great leadership team at my prior company, Return Path, over the course of 20 years. Within that long block of time with many executives, there was a particular period of time, roughly 2004-2012, that I jokingly refer to as the “golden age.” That’s when we grew the business from roughly $5mm in revenue to $50 or $60mm. The remarkable thing was that we executed that growth with the same group of 5-6 senior executives. A couple new people joined the team, and we struggled to get one executive role right, but by and large one core group took us from small to mid-sized. Why? We looked at each other — literally, in one meeting where we were talking about professional development — and said, “we have to commit to individual coaching, to team coaching, and to growth as leaders, or the company will outpace us and we’ll be roadkill.”

That set us on a path to focus on our own growth and development as leaders. We were constantly reading and sharing relevant articles, blog posts, and books. We engaged in a lot of coaching and development instruments like MBTI, TKI, and DISC. We learned the value of retrospectives, transparent 360s, and a steady diet of feedback. We challenged ourselves to do better. We worked at it. As one of the members of the Golden Age said of our work, “we went to the gym.”

The “Grow or Die” mantra is real. You can’t possibly be successful in today’s world if you’re not learning, if you don’t have a growth mentality. You are never the smartest person in the room. The minute you are convinced that you are…you’re screwed.

If you don’t believe me, look at the development of your business itself as a metaphor for your own development as a leader. What happens to your startup if it stops growing?

(You can find this post on the Bolster Blog here)

Does size matter?

It is the age-old question — are you a more important person at your company if you have more people reporting into you?  Most people, unfortunately, say yes.

I’m going to assume the origins of this are political and military. The kingdom with more subjects takes over the smaller kingdom. The general has more stars on his lapel than the colonel. And it may be true for some of those same reasons in more traditional companies. If you have a large team or department, you have control over more of the business and potentially more of the opportunities. The CEO will want to hear from you, maybe even the Board.

In smaller organizations, and in more contemporary organization structures that are flatter (either structurally or culturally) or more dynamic/fluid, I’m not sure this rule holds any more. Yes, sure, a 50-person team is going to get some attention, and the ability to lead that team effectively is incredibly important and not easy to come by. But that doesn’t mean that in order to be important, or get recognized, or be well-compensated, you must lead that large team.

Consider the superstar enterprise sales rep or BD person. This person is likely an individual contributor. But this person might well be the most highly paid person in the company. And becoming a sales manager might be a mistake — the qualities that make for a great rep are quite different from those that make a great sales manager. We have lost a few great sales reps over the years for this very reason. They begged for the promotion to manager, we couldn’t say no (or we would lose them), then they bombed as sales managers and refused as a matter of pride to go back to being a sales rep.

Or consider a superstar engineer, also often an individual contributor. This person may be able to write code at 10x the rate and quality of the rest of the engineering organization and can create a massive amount of value that way. But everything I wrote above about sales reps moving into management holds for engineers as well.  The main difference we’ve seen over the years is that on average, successful engineers don’t want to move into management roles at the same rate as successful sales reps.

It’s certainly true that you can’t build a company consisting of only individual contributors. But that isn’t my point. My point is that you can add as much value to your organization, and have as much financial or psychic reward, by being a rock star individual contributor as you can by being the leader of a large team.

OnlyOnce is 8 years old this week, which is hard to believe. So it is fitting that I got halfway through a new post this morning, then a little alarm bell went off in my head that I had written something similar before.  The topic is around moderation versus extremes.  I first wrote about this topic in 2005 in a post called Shifting Gears but I have thought about it more recently in a different way. 

Instead of phrasing this as a struggle between “Meden Agan,” which is Greek for “everything in moderation,” and “Gor oder gornischt,” which is Yiddish for “all or nothing,” I’d like to focus here on the value of occasionally going to an extreme. And that value is around learning. Let me give three examples:

-We were having a buy vs. build conversation at work a few months back as we were considering an acquisition. Some people in the room had an emotional bias towards buy; others toward build. So we framed the debate this way:  “Would you acquire the company for $1 instead of building the technology?” (Yes!) “Would you buy it for $10mm?” (No!) Taking the conversation to the extremes allowed us to focus on a rational answer as opposed to an emotional one — where is the price where buy and build are in equilibrium?

– With my colleague Andrea, I completed a 5-day juice fast a few weeks back. It was good and interesting on a bunch of levels. But I came away with two really interesting learnings that I only got from being extreme for a few days:  I like fruits and veggies (and veggie juices) a lot and don’t consume enough of them; and I sleep MUCH better at night on a relatively empty stomach

– Last year, I overhauled my “operating system” at work to stop interviewing all candidates for all jobs and stop doing 90-day 1:1 meetings with all new employees as well. I wrote about this in Retail, No Longer. What finally convinced me to do it was something one of my colleagues said to me, which was “Will you be able to keep these activities up when we have 500 employees?” (No) “So what is the difference if you stop now and save time vs. stopping in 6 months?” Thinking about the extreme got me to realize the full spectrum

It may not be great to live at the extremes, but I find extremes to be great places to learn and develop a good sense of what normal or moderate or real is.

Job 1

The first “new” post in my series of posts about Return Path’s 14 Core Values is, fittingly,

Job 1:  We are all responsible for championing and extending our unique culture as a competitive advantage.

The single most frequently asked question I have gotten internally over the last few years since we grew quickly from 100 employees to 350 has been some variant of “Are you worried about our ability to scale our culture as we hire in so many new people?”  This value is the answer to that question, though the short answer is “no.”

I am not solely responsible for our culture at Return Path. I’m not sure I ever was, even when we were small.  Neither is Angela, our SVP of People.  That said, it was certainly true that I was the main architect and driver of our culture in the really early years of the company’s life.  And I’d add that even up to an employee base of about 100 people, I and a small group of senior or tenured people really shouldered most of the burden of defining and driving and enforcing our culture and values.

But as the business has grown, the amount of responsibility that I and those few others have for the culture has shrunk as a percentage of the total.  It had to, by definition.  And that’s the place where cultures either scale or fall apart.  Companies who are completely dependent on their founder or a small group of old-timers to drive their cultures can’t possibly scale their cultures as their businesses grow.  Five people can be hands on with 100.  Five people can’t be hands on with 500.  The way we’ve been able to scale is that everyone at the company has taken up the mantle of protecting, defending, championing, and extending the culture.  Now we all train new employees in “The RP Way.”  We all call each other out when we fail to live up to our values.  And the result is that we have done a great job of scaling our culture with our business.

I’d also note that there are elements of our culture which have changed or evolved over the last few years as we’ve grown.  That isn’t a bad thing, as I tell old-timers all the time.  If our products stayed the same, we’d be dead in the market.  If our messaging stayed the same, we’d never sell to a new cohort of clients.  If our values stayed the same, we’d be out of step with our own reality.

Finally, this value also folds in another important concept, which is Culture as Competitive Advantage.  In an intellectual capital business like ours (or any on the internet), your business is only as good as your people.  We believe that a great culture brings in the best people, fosters an environment where they can work at the top of their games even as they grow and broaden their skills, increases the productivity and creativity of the organization’s output through high levels of collaboration, and therefore drives the best performance on a sustained basis.  This doesn’t have to be Return Path’s culture or mean that you have to live by our values.  This could be your culture and your values.  You just have to believe that those things drive your success.

Not a believer yet?  Last year, we had voluntary turnover of less than 1%.  We promoted or gave new assignments to 15% of our employees.  And almost 50% of our new hires were referred by existing employees.  Those are some very, very healthy employee metrics that lead directly to competitive advantage.  As does our really exciting announcement last week of being #11 in the mid-sized company on Fortune Magazine’s list of the best companies to work for.

Two Ears, One Mouth

Brace yourself for a post full of pithy quotes from others.  I’m not sure how we missed this one when drafted our original values statements at Return Path years ago, because it’s always been central to the way we operate.  We aren’t just the world’s biggest data-driven email intelligence company – we are a data-driven organization.  So another one of our newly written Core Values is:

Two Ears, One Mouth:  We ask, listen, learn, and collect data.  We engage in constructive debate to reach conclusions and move forward together.

I’m not sure which of my colleagues first said this to me, but I’m going to give credit to Anita, our long-time head of sales (almost a decade!), for saying “There’s a reason God gave you two ears and one mouth.”  The meaning?  Listen (and look, I suppose) more than you speak.

This value really has two distinct components to it, though they’re closely related.  First, we always look to collect data when we need to understand a situation or make a decision.  To quote our long-time investor, Board member, and friend Brad Feld, “the plural of anecdote is not data.”  That means we are always looking far and wide for facts, numbers, and multiple perspectives.  Some of us are better than others at relying on second-hand data and observations from trusted colleagues, which means often times, many of us are collecting data ourselves to inform a situation.  But regardless, we always start with the data.

Second, we use data as the foundation of our decision-making process.  I heard another great quote about this once, which is something like, “If we are going to make a decision based on data, the data will make the decision for us.  If we’re going to use opinion, let’s use mine.”  And while I’m at it, I’ll throw in another great quote from Winston Churchill who famously said “Facts are stubborn things.”  While we do have constructive debates all across our organization, those debates are driven by facts, not emotion.

Finally, when this value says that “we move forward together,” that is the combination of the points in the two prior paragraphs.  People may have different opinions entering a debate.  Even with a lot of data behind a decision, they may still have different opinions after a decision has been made.  But we work very deliberately to all support a decision, even one we may disagree with, and we are able to do that, move forward together, and explain the decision to the organization, because the decision is data-driven.

Selecting Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  This is the first one…and Fred’s post on the other side of the topic is here.  Next week, we’ll address the topic of building a successful CEO-VC partnership once it’s established.

If you’re fortunate enough to have built a really strong early stage company, you will find yourself in the position of being able to pick from a number of potential venture investors.  The better your business and the more exciting the space you’re trying to tackle…the more investors you’ll find circling around you.  Here are a few tips for ending up with the best long-term partner as an investor.

1. Look for VC portfolios that have a lot of “like” companies (B2B, B2C, media, tech, etc.).  One of the strongest points of value that venture investors bring to the table is pattern matching, and you can maximize that by making sure the investor you end up with has seen a multitude of companies like yours
2. Check references carefully.  Don’t be shy – prospective VCs are checking up on you, and you have every right to do the same with them.  When Fred first invested in Return Path, he gave me a list of every CEO he had ever worked with and said “Call anyone you want on the list.  Some of these guys I worked well with, a couple I fired.  But they’ll all tell you what I’m like to work with.”  First prize is the VC who volunteers this information.  Second prize is the VC who gives it to you when you ask.  A distant third price is the VC who gives you two names and ask for time to prep them ahead of time
3. Focus on the person first, the firm second.  Having a good venture firm is important.  But at the end of the day, you’re dealing with a person first and foremost.  That’s who will be on your board giving you advice and measuring your performance.  Better to have an A person at a B firm than a B person at an A firm (of course, even better to have an A person at an A firm).  This means two things – selecting a great person to be on your Board, and also making sure you end up with a person who has enough juice within his or her firm to get things done on your behalf with the partnership
4. Always have a BATNA (Best Alternative to a Negotiated Agreement – a fancy way of saying Plan B).  This is probably the most important piece of advice I can offer.  And this is true of any negotiation, not just a term sheet.  It’s often said that good choices come from good options. Sometimes, you have to walk away from a deal where you’ve invested a lot of time, energy, and emotion.  But as an entrepreneur, you can mitigate the number of times you have to walk away by developing good alternative options to a particular deal. That way, if one option doesn’t pan out as you’d hoped, another very good option is waiting in the wings.  If you negotiate with two or three VCs, you’ll have a great backstop and won’t let the emotional investment in the deal get the best of you.  Yes, you will spend twice to three times the amount of time on the process, but it’s well worth it
5. Don’t be swayed by promises of help.  I’ve heard VCs say it all.  They’ll help you fill out your management team.  They’ll get you customers.  They’ll help with your back office.  They’re loaded up with value-add.  If venture investor has staffed his or her firm with support personnel who are available free of charge to portfolio companies (this does happen once in a while), then assume your VC will be as helpful as possible, but no more or less helpful than another investor
6. Handle the negotiation yourself, in person as much as possible.  The best way to get to know someone’s character is to negotiate a deal with him.  This gives you lots of opportunities to look for reasonableness, and to see if he or she is able to focus on the big picture.  The biggest warning sign to look for is someone who says things like “you have to agree on this term, because this is how we always do deals.”  By the way, how you handle yourself in this negotiation is equally important.  The financing is the line of demarcation between you and the VC courting each other, and the VC joining your board and effectively becoming your boss
7. “Pay up” for quality and for a clean security.  There is a world of difference between good VCs and bad VCs (both the individual partners and the firms) that will ultimately have a lot to do with how successful your company can become.  The quality of your VC isn’t more important than the quality of your product or your team, but it’s right up there.  But – and this is an important but – you should expect to “pay” for quality in the form of slightly weaker terms (whether valuation or type of security).  Similarly, I’d always sacrifice valuation for a clean security.  Everyone always thinks that price/valuation is the most important thing to maximize in a deal. However, the structure of the security can be much more important in the long run.  Whether the VCs buy 33 percent of your company or 30 percent of your company is much less important than having a capital structure that’s easy for an outsider to understand and want to join

As with all things, there are probably another dozen items that could be added to this list, but it’s a good starting point.  However, your more important role as CEO is to put your company in a position where you can select from a number of high quality investors, so start there!

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is different from those same things in first-time founders. Not every single multi-time founder has every single one of these traits, but they all have a majority of them and form a pretty common pattern. I’ve noticed this with non-profit founders as well as for-profit ones.

• They have an Easier Time Recruiting team members and investors. That may sound obvious, but there are significant benefits to it. They also tend to have Much Cleaner Cap Tables, because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!
  
• They have a Big Vision. Once you’ve had an exit, whether successful or not or somewhere in between, you don’t want to focus on something niche. You want to go all-in on a big problem.
  
• They are interested in creating Portfolio Effect. A number of repeat founders want to start multiple business at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.
  
• They are driving to be Efficient in Execution and Find Leverage wherever they can. One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team. At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible.
  
• They are Impatient for Progress. While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…
  
• They are equally Impatient for Success (or Failure). More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of mine says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.
  
• They are Calm and Comfortable in Their Own Skin. At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.
  
• They are stronger at Self Management. They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these traits, or others, in repeat founders?

Stamina

A couple years ago I had breakfast with Nick Mehta, my friend who runs the incredibly exciting Gainsight.  I think at the time I had been running Return Path for 15 years, and he was probably 5 years into his journey.  He said he wanted to run his company forever, and he asked me how I had developed the stamina to keep running Return Path as long as I had.  My off the cuff answer had three points, although writing them down afterwards yielded a couple more.  For entrepreneurs who love what they do, love running and building companies for the long haul, this is an important topic.  CEOs have to change their thinking as their businesses scale, or they will self implode!  What are five things you need to get comfortable with as your business scales in order to be in it for the long haul?

Get more comfortable with not every employee being a rock star.  When you have 5, 10, or even 100 employees, you need everyone to be firing on all cylinders at all times.  More than that, you want to hire “rock stars,” people you can see growing rapidly with their jobs.  As organizations get larger, though, not only is it impossible to staff them that way, it’s not desirable either.  One of the most influential books I’ve read on hiring over the years, Topgrading (review, buy), talks about only hiring A players, but hiring three kinds of A players:  people who are excellent at the job you’re hiring them for and may never grow into a new role; people who are excellent at the job you’re hiring them for and who are likely promotable over time; and people who are excellent at the job you’re hiring them for and are executive material.  Startup CEOs tend to focus on the third kind of hire for everyone.  Scaling CEOs recognize that you need a balance of all three once you stop growing 100% year over year, or even 50%.

Get more comfortable with people quitting.  This has been a tough one for me over the years, although I developed it out of necessity first (there’s only so much you can take personally!), with a philosophy to follow.  I used to take every single employee departure personally.  You are leaving MY company?  What’s wrong with you?  What’s wrong with me or the company?  Can I make a diving catch to save you from leaving?  The reality here about why people leave companies may be 10% about how competitive the war for talent has gotten in technology.  But it’s also 40% from each of two other factors.  First, it’s 40% that, as your organization grows and scales, it may not be the right environment for any given employee any more. Our first employee resigned because we had “gotten too big” when we had about 25 employees.  That happens a bit more these days!  But different people find a sweet spot in different sizes of company.  Second, it’s 40% that sometimes the right next step for someone to take in their career isn’t on offer at your company.  You may not have the right job for the person’s career trajectory if it’s already filled, with the incumbent unlikely to leave.  You may not have the right job for the person’s career trajectory at all if it’s highly specialized.  Or for employees earlier in their careers, it may just be valuable for them to work at another company so they can see the differences between two different types of workplace.

Get more comfortable with a whole bunch of entry level, younger employees who may be great people but won’t necessarily be your friends.  I started Return Path in my late 20s, and I was right at our average age.  It felt like everyone in the company was a peer in that sense, and that I could be friends with all of them.  Now I’m in my (still) mid-40s and am well beyond our average age, despite my high level of energy and of course my youthful appearance.  There was a time several years ago where I’d say things to myself or to someone on my team like “how come no one wants to hang out with me after work any more,” or “wow do I feel out of place at this happy hour – it’s really loud here.”  That’s all ok and normal.  Participate in office social events whenever you want to and as much as you can, but don’t expect to be the last man or woman standing at the end of the evening, and don’t expect that everyone in the room will want to have a drink with you.  No matter how approachable and informal you are, you’re still the CEO, and that office and title are bound to intimidate some people.

Get more comfortable with shifts in culture and differentiate them in your mind from shifts in values.  I wrote a lot about this a couple years ago in The Difference Between Culture and Values . To paraphrase from that post, an organization’s values shouldn’t change over time, but its culture – the expression of those values – necessarily changes with the passage of time and the growth of the company.  The most clear example I can come up with is about the value of transparency and the use case of firing someone.  When you have 10 employees, you can probably just explain to everyone why you fired Joe.  When you have 100 employees, it’s not a great idea to tell everyone why you fired Joe, although you might be ok if everyone finds out.  When you have 1,000 employees, telling everyone why you fired Joe invites a lawsuit from Joe and an expensive settlement on your part, although it’s probably ok and important if Joe’s team or key stakeholders comes to understand what happened.  Does that evolution mean you aren’t being true to your value of transparency?  No.  It just means that WHERE and HOW you are transparent needs to evolve as the company evolves.

• Get more comfortable with process.  This doesn’t mean you have to turn your nimble startup into a bureaucracy.  But a certain amount of process (more over time as the company scales) is a critical enabler of larger groups of people not only getting things done but getting the right things done, and it’s a critical enabler of the company’s financial health.  At some point, you and your CFO can’t go into a room for a day and do the annual budget by yourselves any more.  But you also can’t let each executive set a budget and just add them together.  At some point, you can’t approve every hire yourself.  But you also can’t let people hire whoever they want, and you can’t let some other single person approve all new hires either, since no one really has the cross-company view that you and maybe a couple of other senior executives has.  At some point, the expense policy of “use your best judgment and spend the company’s money as if it was your own” has to fit inside department T&E budgets, or it’s possible that everyone’s individual best judgments won’t be globally optimal and will cause you to miss your numbers.  Allow process to develop organically.  Be appropriately skeptical of things that smell like bureaucracy and challenge them, but don’t disallow them categorically.  Hire people who understand more sophisticated business process, but don’t let them run amok and make sure they are thoughtful about how and where they introduce process to the organization.

I bet there are 50 things that should be on this list, not 5.  Any others out there to share?