If I had to pick one human trait that is the single most impactful in one’s ability to have positive and successful interpersonal relationships, there’s a hands-down winner: Self-Awareness. This is true no matter what kind of relationships you’re talking about — parent, manager, executive, friend, partner or spouse.

Someone shared a framework with me years ago that helps explain why this is true, which I’ve been meaning to blog about for a long time. I found this image, which is close enough to the 2×2 that was once drawn for me on a whiteboard.

The framework is at once incredibly simple and incredibly complex.

Having true self-awareness and the ability to be reflective, to take in input and feedback, and the ability to accurately self-assess is where it all starts. “I am unhappy today,” “I am doing a bad job right now,” “I am not good at doing this task” are all pretty difficult things to say to yourself. And yet, without those, it’s impossible to progress through this framework.

I learned this framework where boxes II and III in what you see in this graphic are the other way around, but I’m not sure that matters as much as box I being first and box IV being last.

Once you have a solid level of self-awareness, you can exert some level of self-control. That’s not a guarantee — self-control is its own animal, but you can’t manage what you can’t understand. Empathy is similarly a follow-on to self-awareness, but also its own trait. How can you possibly understand what someone else is going through if you don’t understand what you’re going through?

The final box — Influence — is the result of building on all three of the prior traits. It’s impossible to influence others, to have deep and lasting relationships, and to be able to work productively together, without having a solid level of empathy and self-control.

You can be a leader without any of these traits if you’re an autocrat, whether a political one or a corporate one. If people MUST listen to you, then you can tell them what to do. But founders, especially ones who control their companies, shouldn’t be under the misapprehension that they are influencing others if what they’re really doing is ordering them around.

Can self-awareness be taught, or is it something you’re either born with or not? While most traits have a balance of nature and nurture, I am a big believer that self-awareness can largely be learned over time, so let’s call it a 10/90 on the nature/nurture scale. I’ve had a lot of influencers in my life who have, in their own ways helped me learn the practice of self-awareness, from my parents, to the professor in college who gave me my first 2×4, to my first couple of managers in my early jobs, Neal and Eleanor, to my coach, Marc who gave me my first 360, to my long-time colleagues along the way at Return Path and Bolster, to my wife, Mariquita, even to my kids. I’m sure I’m forgetting many others along the way. I’m thankful to all of them.

Want to improve your practice of management? Leadership? Collaboration and teamwork?

It all starts with self-awareness.

I just finished up a coaching call with a late-stage CEO client, and we were talking about a situation where he helped tee up a couple successes for a new senior executive on his team and then promptly gave the exec credit for the successes. That’s good form as a leader – you take the blame when things go wrong but give away credit when things go well.

But my client articulated a selfish reason to this that goes beyond the “good leadership form” argument that I’d never thought of before:

“When you give them the credit, you win twice.”

What he meant by that is that you get your first win when you bolster the person on your team by giving them the win. And you get your second win when others (the rest of the team, your board, etc.) see the goodness that happened and realize that it happened on your watch as the CEO — either by hiring the person who got the credit, or by orchestrating the broader scenario.

After all, who doesn’t want to win twice?

My latest book (I’m a co-author along with Brad Feld and Mahendra Ramsinghani), Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, is now live on Amazon – today is publication day! The book is a major refresh of the first edition, now eight years old. I was quoted in it extensively but not an official author – Brad and Mahendra were nice enough to share that with me this time. The book includes a lot of new material and new voices, including a great Foreword by Jocelyn Mangan from Him for Her and Illumyn. It’s aligned with Startup CEO and Startup CXO in look and in format and is designed to be an easy-to-read operator’s manual to private company boards of directors. Brad also blogged about it here.

We’ve done a lot of work around startup boards at Bolster the past couple of years, including working with over 30 CEOs to help them hire amazing new independent board members. Our landmark Board Benchmark study last year highlighted the problem with startup boards, but also the opportunity that lies within: not enough diversity on the boards, but also not nearly enough independent directors — and a lot of open seats for independent directors that could be filled. That conclusion led me to my Startup Board Mantra of 1-1-1: Independent directors from Day 1, 1 member of the management team, and 1 independent for every 1 investor.

As we posted on the Bolster blog last week, our quick refresh of the Board Benchmark study revealed some good news and some bad news about progress on diversity in the boardroom with startups. The good news is that the needle is starting to move very slowly, and that independent directors present the best opportunity to add diversity to boards. Our data shows that half of all new directors brought onto boards in the last year were independents, and of those, 57.9% were women and 31.6% were non-White board members. Those numbers are well above the prior study’s benchmarks of 36% and 23%, respectively (our experience running board searches skews even further to women and non-White directors being hired).

The bad news is how slowly the needle is moving — only 20% of open independent board seats were filled over the previous year, which is a lot of missed opportunity. The main takeaway is that while overall representation on boards is still skewed largely White and male, the demographic profile of new board appointments looks a lot different from the representation on boards today, indicating that CEOs are making intentional changes to their board composition.

Startup boards are a great way to drive grassroots change to the face of leadership in corporate America. More CEOs need to follow up by filling their open board seats and fulfilling their stated desires to improve diversity in the boardroom. This takes time and prioritization — these are the places where we see board searches either never get off the ground, or falling down once they do, for all the searches we either run or pitch at Bolster.

Hopefully Startup Boards will help the startup ecosystem get there.

I love stealing/borrowing other people’s good ideas for management and leadership when they’re made public, and I always encourage others to do so from me. I call it “plagiarizing with pride.” So I was intrigued when I saw a new way of doing all-hands meetings published by my friend Daniel Odio (DROdio) on his founder community called FounderCulture. You can see the original post here.

We’ve experimented with different formats and cadences for all-hands meetings over the years. They tend to vary with the size of the company and complexity of the material to cover. Larger companies usually fall into the rhythm of doing quarterly all-hands meetings sometime after the end of the quarter, usually around a Board meeting, with a quarterly recap and forecast for next quarter.

But for early stage companies, there’s no tried-and-true method. We struggled with that for a while at Bolster. Weekly felt too much. Quarterly felt like too little. It seemed weird for me or my co-founders to just have a meeting where we talked at everyone…and it also seemed weird to just host an “open mic night” type meeting. Then I saw DROdio’s video, and we adapted it. It’s working pretty well for us. Here’s what we do in what we’re calling our Open All-Hands Meeting:

• We hold an all-hands meeting every Monday for :30
• A different team member is responsible for being the host/chair/emcee for each meeting
• We run the meeting off of a dedicated Trello board with specific columns of information. Everyone is invited to contribute to the Trello board in the days leading up to the meeting. The columns are:
  • Values-Kudos-Good News: Anyone can call out anyone for doing something that demonstrates one of the company’s values, that is just a big thank you, or that is some other piece of karmic goodness they want to share
  • Wins: All client wins are shown here with some detail, each in its own card with its owner highlighted
  • #MAD: This is where we trade items on which we Made A Decision during the prior week, big or small. We’ve always struggled with the best way to keep everyone informed on things like this…and this works really well for that purpose
  • Learnings/Product Ideas: Anyone can populate this with anything they want as they go about their work and either come across learnings or product ideas they want to share
  • Announcements: Pretty self-explanatory, any corporate announcement, new employee introductions, etc.
  • Swim Lane Updates: Each we, we ask one or two of our functional or project areas to do a deep dive update — Product, Finance, Sales, Marketing, Ops, etc. — and this is also where we’ll do product demos of newly released functionality
  • Permanent Items: this isn’t a column that’s read…it just warehouses things we want on the board like the schedule of hosts, schedule of swim lane updates, instructions for running the meeting, recordings of prior meetings
  • BOLSTER 2022: this isn’t a column that’s read…it contains our mission, values, strategy, and key strategic initiatives and metrics for the year
  • Archive: this isn’t a column that’s read…it just contains the prior week’s items
• There’s a series of light integrations between Slack, Hubspot, and Trello to automatically populate Trello based on certain channels, keywords, and emojis. Every week, the board is automatically wiped clean after the meeting
• The host moves the meeting from column to column and card to card, sometimes reading the cards, and sometimes asking the person who submitted the card to read it or give color commentary on it
• I do jump in from time to time, as do some of my co-founders or our other leaders, to give extra commentary or amplify something or help connect the dots. But that’s about as formal as my role gets other than…
• …when we do have a quarterly board book and board meeting, I host that one meeting and recap the meeting, ask other leaders to comment on specific topics, and facilitate Q&A on the materials we send out ahead of time. So I’m hosting 4 meetings per year
• The host can add a personal touch to any meeting. Custom wallpaper for the Trello board. Asking everyone in the company who has a pet to send in a photo of the pet ahead of time and introducing their furry friends during the meeting. Playing intro or outro music to fit the occasion. Doing spot surveys or game show questions to keep things lively. Interviewing new team members. Asking everyone to do a one-sentence “here’s what I’m working on this week” at the end of the meeting
• Finally, the host passes the baton from one person to the next each week. No one can escape this responsibility!

In addition to the Open All-Hands Meeting format, I send the company an email every Friday with some musings on the prior week. The content of these varies widely – from “what I did last week,” to “here’s something I saw that’s interesting,” to welcoming new team members with their bios, to customer testimonials. Sometimes other founders write these. They’re a good way to add a personal touch to the operating system of the company — and we also send these to our board and major shareholders every week so they, too, can keep a finger on the pulse.

These two things together are proving to be a good Operating System for keeping everyone informed, aligned, and connected on a weekly basis.

I love having independent directors on my Board.  They are a great third leg of the stool alongside a CEO/Founder and VCs.  They provide the same kind of pattern matching and outside point of view as VCs — but from a completely different perspective, that of an operator or industry expert.  The good ones are CEOs or CXOs who aren’t afraid to challenge you.  Equally important, they’re not afraid to challenge your VCs.  At Return Path, I always had 2 or 3 independent directors at any given time to balance out VCs, and some have become great long term friends like Scott Petry, Jeff Epstein, and Scott Weiss.  At Bolster, we’re already having a great experience with our first independent, Cristina Miller, and we’re about to add a second independent.  And I’ve served as an independent director multiple times.

So as you can imagine, I was shocked by one of the headlines coming out of the Board Benchmark study we ran at Bolster across 250+ clients (detailed blog post with a bunch of charts and graphs) that only ⅓ of companies in the study have any independent directors.  Even larger companies at the Series C and D levels only have independent directors 60% and 67% of the time.  What a missed opportunity for so many companies.

Less surprising, though still sobering, were the numbers on diversity that came out of the study.  79% of the directors in the sample are white.  86% are men.  43% of boards are completely racially homogenous (most all-white) while 80% are mostly racially homogeneous (meaning only one diverse member); 56% are gender homogenous (most all men), while 87% are mostly gender homogenous (only one female).  For an industry that is spending a lot of time talking about diversity in leadership teams and on boards, that’s disappointing.

Here’s the linkage of the two topics:  The solution to the board diversity problem lies in having more independent directors, since management and VC board seats are often both “fixed” and non-diverse.  Independent seats are the easiest to fill with diverse candidates.  Conveniently, more independent directors also leads to higher quality boards.  

In partnership with some DEI experts, our study also includes some suggested actionable tips for CEOs and board leaders, which I encourage you to read. There are really three simple (IMO) steps to having more diverse boards, and there is some good news in the Bolster study around these points:

1. Add independent director seats.  50% of the companies in the survey either have or expect to have an independent board seat open within 12 months.  That’s a good start, but honestly, I can’t imagine running any board without at least 1-2 independent directors (up to 3-4 for larger companies), starting on Day 1.  Given that only ⅓ of companies in the sample have any independent board members at all, the 50% number feels quite low.
   
2. Open the recruiting funnel to include first-time directors.  Historically, companies have mainly targeted current or former CEOs or people who have board experience to be independent directors.  That is a recipe to perpetuate having mostly white male board members.  But Bolster has done a few dozen board searches so far, and 66% of those clients have expressed a willingness to take on first-time directors, as long as they are “board ready,” which we define as having been on any kind of board, not just a corporate board; having reported to a founder or CEO and had regular interaction with and presentations to a board; or having significant experience as a formal or informal advisor.  Once you widen the funnel to include all candidates who meet those criteria, you can very easily have a diverse slate of highly qualified candidates.  Bolster is a great source of these candidates (this is a real focal point for our business), but there are plenty of other online or search firm sources as well.
   
3. Have the courage to limit the number of management/investor board members.  Whether or not you can add independent board members may be a function of how many seats you have to play with in your corporate charter.  Of course, you can add seats indefinitely, but there’s no reason to have a 7-person board for your Series A company.  My rule of thumbs on this are simple:  (a) Only one founder member of the management team on the Board – more than that is a waste of a valuable board slot; and (b) VCs should always be less than 50% of your board members, so as new ones roll on, old ones should roll off – or add a VC and an independent at the same time.  Both of these take serious effort and courage, both are worth it, and both probably merit a longer blog post someday.

The Board Benchmark study also had a wealth of information about compensation for independent directors — cash vs. stock, what kind of stock, how much stock, vesting and acceleration provisions. 

Here’s a Slideshare of the full survey results, in case this and/or the Bolster blog link isn’t detailed enough for you:

If you’re interested in learning more, the survey is free to take and all the granular results (including comp benchmarks) are available to benchmark against your company if you take it. Just email me if you’re interested at [email protected].

I wrote a post the other day about innovating employee benefits practices, and I realized I’d never documented a couple other ways in which we have always tried to innovate People practices. Here’s one of them: the Open Expense Policy, which I wrote about in the second edition of Startup CEO in a new chapter on Authentic Leadership when talking about the problem of the “Say-Do” gap.  Here’s what I wrote:

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

When we started Return Path, we had a similar policy. It was standard issue. But then over time as our culture became stronger and our People First philosophy and approach became something we evangelized more, we realized that traditional expense was at odds with our deeply held value of trusting employees to make good decisions and giving them the freedom and flexibility they needed to do their best work.

So we blew up the traditional policy and replaced it with a very simple one — “use your best judgment on expenses and try to spend the company’s money like it’s your own.” That policy is still in place today for our team at Bolster. We do have people sign off on expense requests that come in through the Expensify system, mostly because we have to, but unless there is something extremely profligate, no one really says a word.

Similar to what happened when we switched to an Open Vacation policy, we had some concerns from managers about employees abusing the new un-policy, so we had to assure them we’d have their back. But do you know what happened when we implemented the new policy? We got a bunch of emails from team members thanking us for trusting them with the company’s money. And the average amount of expenses per employees went down. That’s right, down. Trusting people to exercise good judgment and spend the company’s money as if it was their own drove people to think critically about expenses as opposed to “spend to the limit.”

I don’t think in 15+ years of operating with an Open Expense policy that any of us have had to call out an employee’s expenses as being too high more than once or twice. That’s what the essence of employee trust is about. Manage exceptions on the back end, don’t attempt to control or micromanage behavior on the front end.

Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief Privacy Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling.

There are a few high-quality ways I’ve typically spent the most time or gotten the most value out of Chief Privacy Officers over the years. Part of it may have to do with the business we were in at Return Path (and now, Bolster), but part of it is understanding what the Chief Privacy Officer needs from the business and working with them in that arena.

For example, I found it helpful to work with the Chief Privacy Officer to help them to deeply understand our business.  Part of what I think we got right in this regard at Return Path was that we almost always made this a fractional role that was combined with other responsibilities — Tom Bartel, Dennis Dayman, and Margot Romary almost always did other senior jobs in operations or product as well.  This is what most likely enabled us to play more offense with the function rather than play defense. Even with an operation or product background, the Chief Privacy Officer is typically focused on external threats and issues and I have found that working with them on business issues not only raises their knowledge, but helps them understand potential security risks.

Another thing I did was to role model training and compliance.  If you mention of the word “compliance” to just about anybody in the organization, you’ll see that it doesn’t usually get anyone’s juices flowing. But it’s important for the company to live up to its obligations with customers and with its own internal policies and we found that if we involved a certain amount of employee training every year around compliance, we were able to build skills and stay on top of changing dynamics.  I always try to be the “first done” on an online training course and make sure to follow related policies so that our Chief Privacy Officer has air cover…and so that I can ask others to do the same with a clear conscience.

During a crisis.  I may interact with Privacy infrequently, but oftentimes when I do, it’s because something has gone wrong, or we’re worried about something going wrong.  That’s ok!  As long as you can be there to support your Chief Privacy Officer on an emergency response basis and practice some level of servant leadership in a crisis (“how can I help here…who do you need me to call?”), you’re doing your best work in this department.

It’s important to have a regular cadence and a strong relationship with the Chief Privacy Officer because when a crisis hits you don’t want to miss any steps. While most of the time things run smoothly in the Privacy domain, the few times when things spin out of control those are the exact moments when you need to hit the ground running, trust your Chief Privacy Officer, and help get everything sorted out.

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

Book Short:  Awesome Title, So-So Book

Strategy and the Fat Smoker (book, Kindle), by David Maister, was a book that had me completely riveted in the first few chapters, then completely lost me for the rest.  That was a shame.  It might be worth reading it just for the beginning, though I’m not sure I can wholeheartedly recommend the purchase just for that.

The concept (as well as the title) is fantastic.  As the author says in the first words of the introduction:

We often (or even usually) know what we should be doing in both personal and professional life.  We also know why we should be doing it and (often) how to do it.  Figuring all that out is not too difficult.  What is very hard is actually doing what you know to be good for you in the long-run, in spite of short-run temptations.  The same is true for organizations.

The diagnosis is clear, which is as true for organizations as it is for fat people, smokers, fat smokers, etc.  The hard work (pain) is near-term, and the rewards (gain) are off in the future, without an obvious or visible correlation.  As someone who has had major up and down swings in weight for decades, I totally relate to this.

But the concept that

the necessary outcome of strategic planning is not analytical insight but resolve,

while accurate, is the equivalent of an entire book dedicated to the principle of “oh just shut up and do it already.”  The closest the author comes to answering the critical question of how to get “it” done is when he says

A large part of really bringing about strategic change is designing some new action or new system that visibly, inescapably, and irreversibly commits top management to the strategy.

Right.  That’s the same thing as saying that in order to lose weight, not only do you need to go on a diet and weigh yourself once in a while, but you need to make some major public declaration and have other people help hold you accountable, if by no other means than causing you to be embarrassed if you fail in your quest.

So all that is true, but unfortunately, the last 80% of the book, while peppered with moderately useful insights on management and leadership, felt largely divorced from the topic.  It all just left me wanting inspirational stories of organizations doing the equivalent of losing weight and quitting smoking before their heart attacks, frameworks of how to get there, and the like.  But those were almost nonexistent.  Maybe Strategy and the Fat Smoker works really well for consulting firms – that’s where a lot of the examples came from.  I find frequently that books written by consultants are fitting for that industry but harder to extrapolate from there to any business.

(Post 4 of 4 in the series on Scaling CROs – other posts are, When to Hire your First Chief Revenue Officer, What Does Great Look like in a Chief Revenue Officer and Signs your Chief Revenue Officer isn’t Scaling)

Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent.

One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events.  Particularly if you’re a B2B company that engages with clients during the sales process, you’ll probably find yourself at a lot of client meetings and events, either internal or external.  Your CRO will be there, too, which gives you a great opportunity to spend large blocks of time together in transit, or a good deal of time together socially. One thing we learned during the work-at-home pandemic is just how much time we save by not traveling.  So when life resumes to normal, why waste time in an Uber or on a plane when you can have a deep strategic conversation or even a personal/social one with one of your senior executives? Of course, you have to actually be more proactive in meeting with your CRO since you won’t have events that naturally bring you together, but I’ve found that the early morning time in the hotel gym or late-night drink in the lobby bar before heading up to bed now translates to time I can have with my CRO. 

Another way to engage with the CRO is In a Weekly Forecast meeting.  Jeff Epstein, former CFO of Oracle, was one of my long-time board members at Return Path and he helped us architect a new core business process once our sales team got large and mature and geographically disparate enough that it was hard for us to have a solid forecast.  Both me and our CFO engaged in the Weekly Forecast meeting and because of that we forced the discipline of a good roll-up of all regions and business units. The CRO and all sales managers attended and knew that we were paying attention to the numbers and trends and asking tough questions. Our attendance was a forcing function for the CRO so that they organized a pre-meeting the prior day with all teams and units to prepare, and that in and of itself had a cascading effect through the organization of adding discipline, rigor, and accuracy to the forecast.  It also made me a lot more empathetic to my CRO’s issues with respect to the sales leadership team.

Finally, the other way that I engaged with the CRO was ad hoc, either internally or in-market.  My most successful heads of sales have been good at winding me up and pointing me at things as needed, whether that means getting on a plane or Zoom to help close a deal or save a client, or doing a 1:1 mentoring session with a key employee. So, not all interactions with the CRO have to be initiated by the CEO, and a great CRO will use the CEO, leverage their time, when it’s needed.

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

(Post 1 of 4 in the series of Scaling CPDO’s).

For most startups the idea of hiring a CBDO is a pipedream, it’s a role that only global corporations have, right? After all, strategic partnerships and M&A are rare events for a startup and can be handled by the founder/CEO, or potentially by someone in Sales.  If a startup is partner or channel heavy, those areas may be the focus of the Sales team in general.  Or, if there is sporadic M&A activity that can be handled by external advisors or bankers. So how do you know when it’s time to hire your first CBDO?

You know it’s time to hire a CBDO when you are spending too much of your own time on things that a CBDO could be doing. When a deal shows up, it’s a mountain of work because there are countless meetings and conversations both internal and external to the company and with your board; there’s a ton of due diligence that needs to be done, and there’s always thinking about the strategic roadmap moving forward. The problem is that you can’t control when a deal shows up but once it does, a series of processes and tasks that are time-dependent kick in and it can consume all of your bandwidth. It’s worth it to hire a CBDO if you think you’re only going to do one deal just to take all that effort off your plate.

Another sign that you should hire a CBDO is if your board asks you for your M&A roadmap, and you don’t have a great answer and aren’t sure how to get to one. For a startup the stratetgic roadmap might just be to grow the company any way they can, but for a scaleup you’ll have to be much more thoughtful about strategic growth, you’ll need to have metrics, benchmarks, and timelines, you’ll need to know whether you can hit those milestones organically or whether you need to partner, acquire, or sell off parts of the business. A CBDO not only thinks about all the nuances of a stratetgic roadmap, but has done the work to make it easy to pull the trigger when the opportunity arises.

A more practical solution for many startups is to consider a fractional CBDO. A fractional CBDO may be the way to go if you need help defining your partnership or M&A strategy, or you need help creating a market map and you don’t want to rely on an external advisor or banker for those. A fractional CBDO can also help execute a couple of M&A transactions that are too small for a banker so if you’re not sure about whether or not a full-time CBDO makes sense for you, you can experiment with smaller deals first. A fractional CBDO could also help define a major new strategic building block like “creating an indirect sales channel” or “international expansion,” and work with you and your whole leadership team together to create that, especially if no one at your company has experience in doing that. 

You can find this post on the Bolster Blog here.

Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!”  I thought about it more after and came up with five reasons why. 

First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here. 

Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.

Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more.  This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different. 

The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in.  When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product.  But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer.  In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product.  At Bolster, we have three user personas — Member, Client, and Partner.  And I’m all three of them.  I’m constantly in the product, multiple times a day.  I’m deeply familiar with all angles of the executive search and board building process.  It’s MUCH better to be this close to the product, and the same is true for many of our team members.

Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic.  I love working with clients.  I love talking to members.  I love advising and coaching CEOs. I love being a pretend product manager.  I love writing marketing copy.  It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)

I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.