Counter Cliche:  How Much Paranoia is Too Much Paranoia?

Fred’s VC cliche of the week this week, Opening the Kimono, is a good one.  He talks about how much entrepreneurs should and should not disclose when talking to VCs and big partners — companies like Microsoft or Google, for example.

In response to another of Fred’s weekly cliche postings back in April, I addressed the issue of opening the kimono with VCs in this posting entitled Promiscuity.  But today’s topic is the opposite of promiscuity, it’s paranoia.

I was talking with a friend a few months back who’s a friend and fellow CEO of a high profile, larger company in a similar space to Return Path.  He was obsessing about the secrecy surrounding the size of his business and wouldn’t tell me (a friend) how much revenue his company had, even within a $20mm band.

He pursued this secrecy pretty far.  He never shared financials with his employees.  He never told anyone the metrics, not even his close friends and family.  He even withdrew his company from consideration for a high-profile award for growth companies which it had entered into and won in prior years since someone might be able to string together enough years of data to compute their size.

Why?  Because he didn’t want any venture capitalists to figure out how big they had gotten and decide to throw money at upstart competitors.  Talk about a closed kimono!

I’m much more open book than that with Return Path, but I have a tremendous amount of respect for this guy, so I gave the matter some thought.  There are certainly some situations which call for discretion, but I couldn’t come up with too many that would drive my guiding principle to be secrecy.

1. Being “open book” with employees is essential.  Your people need to know where the business stands and how their efforts are contributing to the whole.  More important, they need to know that you trust them.

2. Using some key metrics to promote your company can be very helpful.  I challenge you to show me a marketing person who doesn’t want to brag about how big you are, how many customers you have, what market share you have.

3. There’s no reason to worry about Venture Capitalists.  Sure, they can fund a competitor, but they’ll do that without knowing exactly how much revenue you have, how quickly.  The good ones are good at sniffing out market opporunities ahead of time.  The bad ones, you care about less anyway.

4. All that said, you can never be paranoid enough about the competition.  Assume they’re all out to get you at every turn, that they’re smarter, richer, quicker, and better looking than you are.  Live in fear of them eating your lunch.

Paranoia is healthy (just ask Andy Grove), but it does have its limits around the basics of your business, and around how you treat employees.

RSS Advertising

This is two-day-old news by now, but in case you missed it, we just announced than we – Return Path – are partnering with Feedburner to take RSS advertising to the next level (coverage here, here, and here).

As you probably know if you receive my feed or other ones, Feedburner has been doing some experimenting with ad units at the bottom of feeds for months now, first using Amazon and more recently Google AdSense to serve up ads.  And as you may know if you look at ads closely, neither of those services has done a great job making the ads truly relevant.  I can’t tell you, for example, the number of times I write a posting about a book, and the ad has absolutely nothing to do with books, let alone the book or author I’m writing about.  My favorite one was a posting Fred wrote called “Why a Conservative Turns Liberal,” with an ad called “Meet Conservative Singles” — probably not Fred’s intent, although it certainly brought a smile to my face.

Anyway, what we’re doing with Feedburner is very simple.  Our Customer Acquisition Solutions group sells lead generation products to hundreds of advertisers each month in the form of either email list rental or web-based lead gen based on categories of interest expressed by consumers who sign up with our Postmaster Direct service.  Feedburner has categorized a number of the 100,000+ feeds they publish as “Consumer Electronics” or “Computing and Technology,” which are two of the strongest categories we have, both in terms of consumers and in terms of advertisers.

So our salesforce is going to add “RSS” as an option for our advertisers in those categories, and we will work with Feedburner to insert demo-targeted ads into select feeds.  We and Feedburner both acknowledge this is an experiment, but we’re very optimistic about the results: the demographics should line up perfectly and provide our advertisers with a new channel as part of their existing campaigns.  I’m sure Dick or someone else at Feedburner will blog about it as well at some point, and if we learn anything  truly interesting after the first few months, we’ll let the world know!

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013.

Today is a special day in my entrepreneurial journey and in the life of the company that I started back in 1999 (last century!), Return Path, as we announce that Return Path has entered into a definitive agreement to be acquired by an exciting new company called Validity.  Press release is here.

Over almost 20 years, we’ve built Return Path into one of the largest and (I think) most respected companies in the email industry.  We’ve had a culture of innovation that has led to some groundbreaking products for our customers and partners to help make email marketing work better for consumers as well as marketers, and to help keep inboxes safe and clean for mailbox providers and security companies.  

But the company is unusual in many respects.  One of those is longevity. I’m not sure how many Internet companies started in 1999 are still private, backed and led by the same team the whole time, and generally in the same business they started in.  Another is our values-driven “People First” culture. From Day 1, we have believed that if we attract and retain and develop and invest in the best people, we will make our customers successful with great products and service, and that if we do right by our customers, we will do right long term by our shareholders.  While I know that not every employee who ever walked through our doors had a great experience, I know most did and hope that all of them realize we tried our best. Finally, I’m proud that our company gave birth to a non-profit affiliate Path Forward a few years back at the hands of executives Andy Sautins, Cathy Hawley, and Tami Forman.  Path Forward helps parents get back to work after a career break and helps companies improve their gender diversity and hiring biases and has already been a game changer for dozens of companies and hundreds of women.

Today, Return Path serves almost 4,000 customers in almost every country on the globe, with $100 million in revenue, profitable, and excited about the next leg of our brands’ and our products’ lives in the care of Validity.  If you haven’t heard of Validity before today, watch out – you will hear a LOT about them in the weeks and months ahead. They are an incredibly exciting new company with a vision to help tens of thousands of companies across the globe improve their data quality but also help them use data to improve business results.  That vision, inspired by a new friend, CEO Mark Briggs, is a wonderful fit for Return Path’s products and services and people.

To finish this post where I started, Fred’s exact words in that post which got this blog going were:

What does this mean for entrepreneurs and managers? It means that the first time you run a business, you should admit what you are up against. Don’t let ego get in the way. Ask for help from your board and get coaching and mentoring. And recognize that you may fail at some level. And don’t let the fear of failure get in the way. Because failure isn’t fatal. It may well be a required rite of passage.

All of that is true and has been great advice for me over the years.  But Fred left out one important piece, which is that entrepreneurs need to constantly thank the people around them who either work their butts off as colleagues in the business or who give them helpful advice and coaching.  Return Path’s journey has been a long one, longer than most, and the full list of people to thank is too long for a blog post.

I’ve noted Fred and Brad in this post already and I want to thank them and also thank Greg Sands from Costanoa Ventures, the third member of our “dream team” investor syndicate, for their friendship and unwavering support and good counsel for me and Return Path for almost two decades, as well as many other board members we’ve had over the years including long-time independent directors Jeff Epstein, Scott Petry, and Scott Weiss.

I want to thank my co-founders Jack Sinclair and George Bilbrey, and anyone who has ever been on my executive team, including long-time execs Ken Takahashi, Shawn Nussbaum, Cathy Hawley, Dave Wilby, Anita Absey, Angela Baldonero, Andy Sautins, Louis Bucciarelli, Mark Frein, and David Sieh.  There’s nothing quite like being in the proverbial foxhole with someone during a battle or two or ten to forge a tight bond. I want to thank Andrea Ponchione, my extraordinary assistant for 14 years, who keeps me running, sane, and smiling every day. I want to thank my executive coach Marc Maltz and the members of my CEO Forum for allowing me to be unplugged and for their friendship and advice.  I want to thank all of Return Path’s 430 employees today and over 1,300 ever for their hard work in building our company and culture together and for our 4,000 customers and partners for putting their faith in us to help them solve some of their biggest challenges with email.

Finally, no thank you list for this journey would be complete without saying a special thank you to my wonderful wife Mariquita and kids Casey, Wilson, and Elyse.  They deserve some kind of special honor for being inspirational cabin-mates on the entrepreneurial roller coaster without ever being asked if they were up for it.

This event may inspire me to begin writing more regularly again on OnlyOnce.  Stay tuned!

Counter Cliche:  Ready, Set, Exit

Fred’s VC Cliche of the week is the about the Quick Flip.  My counter to that is Ready, Set, Exit (image from Google Images).

Most quick flips involve a huge element of luck.  For every quick flip out there, there are dozens of companies that thought they’d be quick flips and ended up crashing and burning instead.  Back in 1999, when we started Return Path, another Internet entrepreneur I knew loved the idea so much that he told me to start writing the book then, because I would be able to sell the for $100 million before we even had a product in the market.  He said the title of the book would be Ready, Set, Exit.

We were careful not to behave that way, and that’s one of the reasons we’re still here and doing as well as  we are doing today.

As nice as it is to be an investor or an entrepreneur who falls into a Quick Flip scenario, beware of anyone who’s planning on Ready, Set, Exit, whether you’re being pitched to invest, to join the company, or even to be a customer.  Ready, Set, Exit scenarios can’t be manufactured or counted on (if they could, everyone would do them), and that whole mentality is completely antithetical to the stamina required to build a real company.

I think it’s analogous to what everyone tells you when you’re in junior high or high school:  you’ll never find a girlfriend/boyfriend if you’re out looking for one.

The Phoenix Project:  a novel about IT, DevOps, and Helping Your Business Win, by Gene Kim, Kevin Behr, and George Spafford  is a logical intellectual successor and regularly quotes Eli Goldratt’s seminal work The Goal and its good but less known sequel It’s Not Luck.

The more business books I read, the more I appreciate the novel or fable format. Most business books are a bit boring and way too long to make a single point. The Phoenix Project is a novel, though unlike Goldratt’s books (and even Lencioni’s), it takes it easy on the cheesy and personal side stories. It just uses storytelling techniques to make its points and give color and examples for more memorable learning.

If your organization still does software development through a waterfall process or has separate and distinct development, QA, and IT/Operations teams, I’d say you should run, not walk, to get this book. But even if you are agile, lean, and practice continuous deployment, it’s still a good read as it provides reminders of what the world used to be like and what the manufacturing-rooted theories are behind these “new” techniques in software development.

I am so glad our technology team at Return Path, led by my colleagues Andy Sautins and David Sieh, had the wisdom to be early adopters of agile and lean processes, continuous deployment many years ago, and now dockers. Our DevOps process is pretty well grooved, and while I’m sure there are always things to be done to improve it…it’s almost never a source of panic or friction internally the way more traditional shops function (like the one in the book). I can’t imagine operating a business any other way.

Thanks to my long time friend and Board member Greg Sands of Costanoa Venture Capital for suggesting this excellent read.

Lean In, Part II

My post about Sheryl Sandberg’s Lean In a couple months ago created some great dialog internally at Return Path.  It also yielded a personal email from Sheryl the day after it went up encouraging me to continue “talking about it,” as the book says, especially as a male leader.  Along those lines, since I wrote that initial post, we’ve had a few things happen here that are relevant to comment on, so here goes.

We partnered  with the National Center for Women & IT to provide training to our entire organization on unconscious bias.  We had almost 90% of the organization attend an interactive 90 minute training session to explore how these biases work and how to discuss these issues with others.   The goals were to identify what unconscious bias is and how it affects the workplace, identify ways to address these barriers and foster innovation, and provide practice tools for reducing unconscious biases.   While the topic of unconscious bias in the workplace isn’t only about gender, that’s one major vector of discussion.  We had great feedback from across the organization that people value this type of dialog and training.  It’s now going to be incorporated into our onboarding program for new employees.

Second, as I committed to in my original post, we ran a thorough gender-based comp study.  As I suspected, we don’t have a real issue with men being paid more than women for doing the same job, or with men and women being promoted at different rates.    That’s the good news.  However, the study and the conversations that we had around it yielded two other interesting conclusions.  One is that that we have fewer women in senior positions than men, though not too far off our overall male:female ratio of 60:40.  On our Board, we have no women.  On our Executive Committee, we have 1 of 10 (more on this below).  On our Operating Committee, we have 8 of 25.  Of all Managers at the company, we have 32 of 88.  So women skew to more junior roles.

The other is that while we do a good job on compensation equity for the same position, it takes a lot of deliberate back and forth to get to that place.  In other words, if all we did was rely on people’s starting salaries, their performance review data, and our standard raise percentages, we would have some level of gender-based inequality.  Digging deeper into this, it’s all about the starting point.  Since we have far more junior/entry level women than men, the compensation curve for women ends up needing to be steeper than that of men in order to level things out.  So we get to the right place, but it takes work and unconventional thinking.

Finally, I had an enlightening process of recruiting two new senior executives to join the business in the past couple of months.   I knew I wanted to try and diversify my executive team, which was 25% female, so I made a deliberate effort to focus on hiring senior women into both positions.  I intended to hire the best candidate, and knew I’d only see male candidates unless I intentionally sourced female candidates.  For both positions, sourcing with an emphasis on women was VERY DIFFICULT, as the candidate pools are very lopsided in favor of men for all the reasons Sheryl noted in her book.  But in both cases, great female candidates made it through as finalists, and the first candidate to whom I offered each job was female – both superbly qualified.  In both cases, for different reasons I can’t go into here, the candidates didn’t end up making it across the finish line.  And then in both cases, when we opened up the search for a second round, the rest of the candidate pool was male, and I ended up hiring men into both roles.  Now my resulting exec team is even more heavily male, which was the opposite of my intention.  It’s very frustrating, and it leaves us with more work to do on the women-in-leadership topic, for sure.

So…some positives and some challenges the last few months on this topic at Return Path.  I’ll post more as relevant things develop or occur.  We are going to be doing some real thinking, and probably some program development, around this important topic.

Last week, I wrote about Bringing People Along for The Ride by involving people in the process of ideating and creating change in your organization. That’s the most important thing you can do to make it easy for people to handle change.

But what about the people you don’t or can’t bring along for the ride in that way? If you organization has more than 10 people in it, there will inevitably be people where you’re IMPOSING CHANGE ON THEM. And honestly, even people who are involved in designing change still have to live through its impact.

Today’s post is about managing the actual impact.

The best thing you can do as a leader in helping your organization navigate change is to be empathetic to the fact that, even if you involve people in designing the solution, you are, in fact, making changes to their day to day lives. One of the best books I’ve ever read on this is Transitions: Making Sense of Life’s Changes, by William Bridges. And while there’s a lot more to the book than this one point, I’ll share two graphics from the book and its offshoots that say a lot.

Bridges’ basic concept is to think about changes as having three phases. The end of the old thing, the beginning of the new thing, and the time between the two – when the new thing has been announced, but the it hasn’t taken effect yet. Here’s a look at one powerful graphic on this front, where the point is that productivity (the red line) tanks briefly during the time of uncertainty with the overlay of human emotions at each phase.

Next let’s look at Bridges’ model for how to think about these three phases. This part is critical. They are not discrete phases, where everyone finished “ending” and moves onto “neutral” and then moves on to “new.” From the moment a change is in the offing, until after the change is implemented, people are simultaneously operating in all three zones at the same time, in different proportions.

That means when change starts, you’re already helping them understand that there will be a period of confusion followed by a bright new future. And it means that even when the bright new future has arrived, you’re still mindful of the confusion as well as the things that were special about the past.

I wrote about this a little bit in the second edition of Startup CEO and in this blog post on transitions and integration. The paragraph I’ll call out is:

For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years. Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO. Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack. This was a really important way we all got closure on this chapter in our lives

The Baton Pass is a helpful analogy to think about this process. In a relay race, the two runners run alongside each other for a little while until they are at the same pace and proper spot, THEN one hands the other the baton. It’s the time when the past and the future collide, in a neutral zone. When you mark the great things and painful learnings that came before and launch into the bright new future.

The best thing you can do as a leader who is driving change through an organization is to Bring People Along for the Ride. Part of that is involving people in the creation of the new world. But it’s also recognizing that humans have to process change, and that takes time.

Complex Collaborations

I just read a new book entitled Business Without Boundaries:  An Action Framework for Collaborating Across Time, Distance, Organization, and Culture.  I happen to know one of the authors, Don Mankin, who was on our trip to Antarctica last year.  The book is a good, quick read for anyone running an organization that requires any degree of complex collaboration, whether in the form of multiple offices with a single company, close relationships with suppliers or customers or channel partners, or even a joint venture.

Mankin and his co-author Susan Cohen present three case studies:  John Deere, Radica, and Solectron.  They then tie their learnings together into a solid framework that’s almost a how-to checklist for organization leaders to follow.  While the writers take an academic approach, the learnings and framework steps presented are anything but academic — they place a huge premium, for example, on relationship building and communication patterns.  These are all things we’ve worked through over the years at Return Path, whether managing employees across multiple offices  or in working with some of our reseller partners or clients.

All in, it’s a good read — and not just because I hung out with this guy in an igloo for two weeks!

Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

Almost a year into my second journey as a startup CEO at Bolster, and I’m getting more and more questions from other CEOs about what it’s like doing a second startup after almost 20 years at the first one…and achieving pretty good scale by the end.  The short answer is, it’s the same, only it’s way better.  Here’s why.

I’m more confident.  So is our whole founding team.  When Jack and I started Return Path, we were 29.  This time, we were 49 — and the average age of the founders was probably 46 or 47.  The bottom line is that we don’t know everything about the business we’re building, but we know what we’re doing in terms of building a business, a startup, a software company, a service-oriented business, leading a team, planning, executing, and on and on.  Confidence in all of those areas means large portions of our day and brain space are freed up to focus on the actual construction of the business without worrying if we’re doing things right or wrong.

It’s much easier to build a startup today.  1999 wasn’t the dark ages, but it feels like a different millennium in terms of what it’s like to start a technology company from scratch.  The cloud and micro services/APIs mean that we are able to build our platform much more quickly at much lower cost than in the past.  And in terms of tooling the business, we got up and running with about 20 different DIY cloud/SaaS solutions in about 6 weeks for a cost of less than $10k/year.

We are sharper on execution and impatient for success.  Your first startup in your 20s is a lot about “enjoying the startup journey.”  This time around, our team is significantly more focused on critical stage-gate success metrics.  In both cases of course, the objective was to win, but this time around, we are much more focused on getting to that point sooner and with less waste.

We are a lot more productive.  Ok, fine, we’re cheating because of COVID and working from home.  No train commutes.  No plane trips.  No water cooler chatter.  No fluff.  It’s not sustainable, and I’ll write about that more in a future post.  But it’s leading to a surge of productivity like I’ve never experienced or seen before in my career.  I do like to think at least some of it comes from professional maturity — we’ll see when life returns to something more closely approximating normal.

I am having a blast being on the front lines.  I went from running a 500-person company, where I’d honed my job and skill set around communication, people issues, and mobilizing the army to go do things…to spending less than 5% of my time running the company and managing people.  Now depending on the moment, I’m an SDR, a customer success manager, a product manager, and a marketing copywriter.  And probably some other things, too.  And I love every minute of it.  It’s a lot more fun to see the direct impact of my actions on the business as opposed to only really seeing the direct impact of my actions on the people in the business (and occasionally then on some aspect of the business as an individual contributor).

Maybe I’m not having a typical second startup experience.  I know some friends who had successful first exits and hated going back to square one, or failed at a second business and were really disappointed about it, only to shift careers.  But my experience so far is a much better second verse, even though it’s a bit like the first.

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.