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.

I read a ton of books.  I usually blog about business books, at least the good ones.  I almost never blog about fiction or non-business/non-fiction books, but I had a good “what did you read this summer” conversation the other night with my CEO Forum, so I thought I’d post super quick snippets about my summer reading list, none of which was business-related.

If you have kids, don’t read Sheryl Sandberg and Adam Grant’s Option B:  Facing Adversity, Building Resilience, and Finding Joy unless you’re prepared to cry or at least be choked up.  A lot.  It is a tough story to read, even if you already know the story.  But it does have a number of VERY good themes and thoughts about what creates resilience (spoiler alert – my favorite key to resilience is having hope) that are wonderful for personal as well as professional lives.

Underground Airlines, by Ben Winters, is a member of a genre I love – alternative historical fiction.  This book is set in contemporary America – except that its version of America never had a Civil War and therefore still has four slave states.  It’s a solid caper in its own right, but it’s a chillingly realistic portrayal of what slavery and slave states would be like today and what America would be like with them.

Hillbilly Elegy, by J.D. Vance, is the story of Appalachia and white working class Americans as told by someone who “escaped” from there and became a marine, then a Yale-educated lawyer.  It explains a lot about the struggles of millions of Americans that are easy for so many of us to ignore or have a cartoonish view of.  It explains, indirectly, a lot about the 2016 presidential election.

Everybody Lies:  Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are, written by Seth Stephens-Davidowitz, was like a cross between Nate Silver’s The Signal and The Noise and Levitt & Dubner’s Freakonomics.  It’s full of interesting factoids derived from internet data.  Probably the most interesting thing about it is how even the most basic data (common search terms) are proving to be great grist for the big data mill.

P.J. O’Rourke’s How the Hell Did This Happen? was a lot like the rest of P.J. O’Rourke’s books, but this time his crusty sarcasm is pointed at the last election in a compilation of articles written at various points during the campaign and after.  It didn’t feel to me as funny as his older books.  But that could also be because the subject was so depressing.  The final chapter was much less funny and much more insightful, not that it provides us with a roadmap out of the mess we’re in.

Sapiens: A Brief History of Humankind, by Noah Harari, is a bit of a rambling history of our species.  It was a good read and lots of interesting nuggets about biology, evolution, and history, though it had a tendency to meander a bit.  It reminded me a bit of various Richard Dawkins books (I blogged a list of them and one related business topic here), so if you’re into that genre, this wouldn’t be bad to pick up…although it’s probably higher level and less scientific than Dawkins if that’s what you’re used to.

Finally, I finished up the fourth book in the massive Robert Caro quadrilogy biography of Lyndon Johnson (full series here).  I have written a couple times over the years about my long-term reading project on American presidential biographies, probably now in its 12th or 13th year.  I’m working my way forward from George Washington, and I usually read a couple on each president, as well as occasional other related books along the way.  I’ve probably read well over 100 meaty tomes as part of this journey, but none as meaty as what must have been 3000+ pages on LBJ.  The good news:  What a fascinating read.  LBJ was probably (with the possible exception of Jefferson) the most complex character to ever hold the office.  Also, I’d say that both Volumes 3 and 4 stand alone as interesting books on their own – Volume 3 as a braoder history of the Senate and Civil Rights; Volume 4 as a slice of time around Kennedy’s assassination and Johnson’s assumption of power.  The bad news:  I got to the end of Vol 4 and realized that there’s a Vol 5 that isn’t even published yet.

That’s it for summer reading…now back to school!

My dad (one of my main CEO/entrepreneur role models) and I team-teach a business school class in entrepreneurial leadership every year at USD where a friend of his is the professor.  Sometimes I go in person, usually I just do it by video.  We did this a few weeks ago, and my dad talked through a decision-making framework that I’d never heard him mention before.

I sketched it out and really like it and am already using it internally, so I thought I would share it here as well:

To walk through it, delegating decision-making to someone on your team can be as simple as understanding where a decision falls along two different spectrums.  On the vertical axis is “How familiar is the person with this type of decision?” – meaning, has the person seen and made this kind of decision before?  This could be something like firing an employee, signing a contract, negotiating a vendor agreement.  On the horizontal axis is “What are the consequences of getting the decision wrong?” – which is really self explanatory…how big a deal is this?

The primary, upper right quadrant of “The person has made this decision before, and it’s not a huge deal” is an easy one – delegate the decision-making authority.  The two middle quadrants of “big deal, but familiar with the decision” and “never seen this before, but not a big deal” are ripe for the old adage of ask forgiveness later, not permission first, meaning it’s ok to delegate decision-making authority, but hold the person accountable for letting you know about decisions like that so you can be on the lookout for potential required clean-up.

But what I love most is the way my dad framed the final quadrant (lower left here), which is “high stakes decision, never seen this situation before.”  It can be tempting for a senior manager or CEO to just take this quadrant over and remove decision-making authority from a team member.  But it’s also a perfect teaching/coaching moment.  So the rule of thumb for this quadrant is “make the decision with me, but please come to me with a proposal on it.”

And that’s why my dad is such a great business mentor!

I love the concept of Servant Leadership.  From the source, the definition is:

While servant leadership is a timeless concept, the phrase “servant leadership” was coined by Robert K. Greenleaf in The Servant as Leader, an essay that he first published in 1970. In that essay, Greenleaf said:

“The servant-leader is servant first… It begins with the natural feeling that one wants to serve, to serve first. Then conscious choice brings one to aspire to lead. That person is sharply different from one who is leader first, perhaps because of the need to assuage an unusual power drive or to acquire material possessions…The leader-first and the servant-first are two extreme types. Between them there are shadings and blends that are part of the infinite variety of human nature.

“The difference manifests itself in the care taken by the servant-first to make sure that other people’s highest priority needs are being served. The best test, and difficult to administer, is: Do those served grow as persons? Do they, while being served, become healthier, wiser, freer, more autonomous, more likely themselves to become servants? And, what is the effect on the least privileged in society? Will they benefit or at least not be further deprived?“

A servant-leader focuses primarily on the growth and well-being of people and the communities to which they belong. While traditional leadership generally involves the accumulation and exercise of power by one at the “top of the pyramid,” servant leadership is different. The servant-leader shares power, puts the needs of others first and helps people develop and perform as highly as possible.

This is a very broad societal definition, but it’s fairly easy to apply to a more narrow corporate, or even startup environment.  Are you as a CEO oriented primarily towards your people, or towards other stakeholders like customers or shareholders?  By the way, trying to do right by all three stakeholders is NOT a problem in a world of being oriented towards one.  It’s just a philosophy around which comes first, and why.  Our People First philosophy at Return Path is fair clear that at the end of the day, all three stakeholders win IF you do right by employees, so they do the best possible work for customers, so you build a healthy and profitable and growing business.

CEOs who practice Servant Leadership aren’t necessarily focused on power dynamics, or on helping those least privileged in society (at least not as part of their job)…but they are focused on making sure that their employees most important needs are met — both in the moment, as in making sure employees are empowered and not blocked or bottlenecked, and over the long haul, as in making sure employees have opportunities to learn, grow, advance their careers, make an impact, and have the ability to live a well balanced life.

I was in a meeting a couple weeks back with another leader and a few people on his team.  He *seemed* to practice Servant Leadership the way he was speaking to his team members.  But he wasn’t, really.  He was doing something I refer to as Sucking Down.  He was telling them things they clearly wanted to hear.  He was lavishing praise on them for minor accomplishments.  He was smiling and saying yes, when what he really meant was no.  He was practicing the art of Sucking Up, only to people on his team, not to a boss.  I got a sense that something wasn’t right during the meeting, and then post meeting, he actually fessed up to me — even bragged about it — that he was being disingenuous to get what he wanted out of his people.

There’s a clear difference between Servant Leadership and Sucking Down in the long run.  The danger comes in the moment.  Just as managers need to build good detection skills to sniff out evidence of someone on their team Sucking Up, employees need to be able to understand that clear difference in their managers’ behavior as they think about how to manage their careers, and even where to work.

I love that the FTC just banned non-competes, as everyone expected they would. Normally, I’m in favor of small government and fewer regulations, but this is one where I think the government has a legitimate interest in setting up guardrails to a free market.

We started off at Return Path years ago with a standard and fairly benign non-compete because they were standard. But once California banned them and then we started doing business internationally in countries where they were illegal or not customary, we realized it was unfair to treat some employees different than others, so we got rid of them entirely and reverted to the common denominator. We don’t have them at Bolster.

Restricting employees in terms of where they can go work when they leave you is unfair and immoral, in my view. Just because you train an employee and invest in them doesn’t mean you own them. That investment was an exchange for the work that person did for you. There is no such thing as indentured servitude in this country. If you want to keep your employees from leaving you, treat them well and pay them well.

The pendulum has swung way too far on this one, and it was high time for a correction. When the Wall Street Journal says that “Sales staff, engineers, doctors and salon workers are among the most common types of workers affected by litigation of noncompete clauses…in 2022” that makes me sick to my stomach.

Making sure former employees can’t specifically harm you after they leave is a different story.

Some restrictive covenants for a limited period of time for former employees are totally fair. Customer and employee non-solicits for a year – no problem. Non-disclosure of confidential information, trade secrets, and know-how – gotcha. But “you can’t go work at that company because they compete with us” doesn’t work for me.

There are some limited circumstances where non-competes are fair, moral, and make sense. They are more or less relegated to very senior and/or highly specialized people who make a ton of money and large equity stakes in companies who can’t to go to competitor and perform any job at their level without pulling over customer relationships, employee relationships, and know-how and trade secrets. That’s why people at hedge funds and investment banks have “garden leave” where the incoming firm has to pay them to sit on the sidelines for a year before joining. Hopefully those exclusions will remain allowable when all is said and done here.

But by and large, I say good riddance to non-competes. They’re about as American as the metric system and hereditary dictatorships.

The Value of a Break

I’ve written before about our sabbatical policy as well as my experience with my first sabbatical five years ago.

I just got back from another sabbatical. This one wasn’t 100% work-free, which breaks our rule, but after a few false starts with it, when I realized a few weeks before it started in January that I either needed to postpone it again or work on a couple of things while I was on a break, I opted for the latter.  The time off was great. Nothing special or too exotic. A couple short trips, and lots of quality time with Mariquita and the kids.

Re-reading my post from my last sabbatical now, I realize I have re-learned those same three lessons again — that I love my job, my colleagues, and what we are working on.

But I also recognized, in three different ways, the value of a break this time around maybe more than last time.  Maybe it’s that I’m five years older or that I’ve been doing the job for five more years.  Maybe it’s because the last couple of years at work have been incredibly intense and both physically and mentally taxing.  But regardless of cause, the outcome is the same — I return to work today rested, healthy, a little tanner, a few pounds lighter, and with more clarity, resolve, and ideas for work than I’ve had in a long time.

Not only did I recognize this with Return Path on my sabbatical, but during my sabbatical, I also reengaged with two organizations (Princeton and the Direct Marketing Association) where I sit on boards and used to be extremely active but have been pretty dormant for a couple of years. The perspective I gained from that dormant time not only gave me new energy for both, but I think very focused and creative energy that I hadn’t seen in a couple of years.

Even with a little work sprinkled in, 6 weeks off and disconnected from emails, the office, and regular meetings is a blessing that I hope everyone gets to experience at some point in his or her career.

I gave a presentation to a few hundred Return Path employees in January at an all-hands conference we did called “How to Manager Your Career.”

The presentation has three sections — The Three Phases of a Career, How to Get Promoted, and How to Wow Your Manager.

While it’s not as good without the voiceover and interactivity, I thought I’d post it here…see the presentation on Slideshare.

As I said to my audience, if there’s one thing to take away from the topic, it’s this:

Managing your career is up to one, and only one person – you. 

It doesn’t matter how great a corporate culture you have, or how supportive your manager is.  You’re the only person who cares 100% of the time about your career, and you’re the only person with a longitudinal view of what you love, what you’re great at, where you’ve been, and where you want to go.

The Rumors of Email’s Demise Have Been Greatly Exaggerated, Part IV

This one could also be entitled “What Are The Bloggers Smoking?”

Reports from last week’s Blog Business Summit like this one are starting to filter in (pun slightly intended).  This one gets a big yawn from me, even more so than the other times I’ve posted on this subject, here, here, and here.  I’m as much of a blogger and a believer in blogs and RSS as the next guy — maybe even more so — but honestly, people, blogs are going to replace email?

I’d like to address a few critical points here head on, although a large part of me doesn’t even want to dignify yet another empty “email is dead” quote with a response.

Basic error #1. The article seems to confuse blogs with RSS feeds.  RSS feeds are data streams coming into an RSS reader application.  Blogs are web sites.  Hello?!?

Fallacy #1. Because blogs/RSS are interesting new media, email will go away.  To paraphrase my colleague Mike Mayor, why is it that whenever something new comes along, its proponents have to bash the current paradigm to make their thing seem more important?  Let’s go through this one — TV came along, and people said radio would go away.  Cable came along, and everyone said the networks were toast.  The fax machine came along, and FedEx was said to be relegated to legal documents that needed to be signed personally.  The Internet came along, and people said everything else was insignificant (newspapers, TV, radio, snail mail).  So yes, new media do arrive on the scene and perhaps make a dent in all prior media, but I’m having a hard time thinking of that one comes in and clocks another one mano a mano.

Fallacy #2. Spam has made email more difficult, therefore email will go away.  There’s a whole industry out there fighting spam.  I know, I know, just because we want the problem to go away doesn’t mean that we can will it away — but filters are working better by the day (did everyone catch this posting about Postini this week?), false positives can be managed down by vigilant clients working with vendors like Return Path, and whitelists, whenever they start really working and charging money to clients to guarantee delivery, will still leave email as the cheapest medium for targeted commercial messaging out there.

Naive belief #1. Spam has harmed email, but blogs/RSS are immune to the same problems.  I’m sorry, do you think the bad guys, or as Fred always calls it, the Internet Axis of Evil (spam, viruses, spyware, DNS hacking, phishing, and the like) are going to leave blogs and RSS feeds alone?  Not a chance.  The bad guys are already hard at work expanding their Axis of Evil.  There’s already comment spam for blogs (or blam, as some call it).  People have and can hijack RSS feeds (no cool name yet).  There’s Instant Messenger spam (spim).  Last week, I heard about a new one that blew me away, which is that someone figured out how to hijack a Voice Over IP phone call and insert an audio ad/porn into the call (spip).

Naive belief #2. Blogs are truly interactive.  Other than a couple of very popular blogs during the height of last fall’s election, I just don’t think this is true for the mainstream.  There are certainly some people who have a little too much time on their hands who spend hours every day blogging, but most people skim most blogs as one-way communication.   While there are mechanisms for commenting, there aren’t ready mechanisms for publishing comments back to the blog audience (thank goodness), so this medium hasn’t turned out nearly as interactive as people had hoped at the onset.  RSS feeds, in case the writer/speaker was confused in this argument, are completely non-interactive.

Naive belief #3. People will read blogs with an agenda of marketing specific products and services.  The beauty of the blog is that it’s not corporate, and it doesn’t have marketing spin on it.  Blogs are much more journals and publishing tools than marketing vehicles.  Who the heck is going to read a blog on Coke?  Or Nike?  Or Microsoft?  Sure, I might read Howard Shultz’s blog if he had one (his book was good enough), but that’s very different than reading the Starbucks official blog.  Why bother?  Where’s the value there?

Ok, I’m done with today’s rant.  As I said, I love blogging as much as the next guy, but puh-lease!  And for the record, I do believe that RSS feeds and maybe even IM from marketers/publishers will supplement email and in some cases maybe even replace it, but email just isn’t going away any time soon.

Book short:  Proto Gladwell

I’m sure author Robert Cialdini would blanch if he read this comparison, but then again, I can’t be the first person to make it, either.  His book, Influence:  The Psychology of Persuasion, is an outstanding read for any marketing or sales professional, but boy does it remind me of Malcolm Gladwell’s The Tipping Point and Blink (book; blog post).  Of course, Cialdini’s book came out a decade before Gladwell’s!  Anyway, Influence is a great social science look at the psychology that makes sales and marketing work.

Cialdini talks about sales and marketing professionals as “compliance practitioners,” which is a great way to think about them, quite frankly.  He boils down the things that make sales and marketing work to six core factors: consistency, reciprocation, social proof, authority, liking, and scarcity.

Reciprocation – we hate being in a state of being beholden so much that we might even be willing to do a larger favor than the one done for us in order to remove the state.  Think about “free gifts” in merchandising as an example of this, or being in a negotiation where someone trying to make a cold sale on you offers a fallback, smaller sale.  For example, you don’t want to buy anything from the boy scout, but after you say no to the $5 raffle ticket and he asks about the $1 candy bar, you feel more obligated to buy the $1 candy bar because the boy scout has “given” on his initial request.

Consistency – once we have made a choice, personal and interpersonal pressures force us to back it up and justify our earlier decision – even more so when in writing or when declared to others.  This is why marketers love getting testimonials from customers; the testimonial locks the customer in emotionally, as well as encouraging others to buy the product.

Social proof – if others think it’s correct, it must be correct, especially if those other people are like us.  There are some scary examples in the book here, such as Reverand Jim Jones and The People’s Temple mass suicides.  Gripping, but creepy.

Liking – we listen to people we like, and we like people to whom we’re similar or who are physically attractive.  This section was especially reminiscent of Blink, but with different and more marketer-focused examples.

Authority – we have an extreme willingness to listen to authority, even when the authority isn’t quite relevant.  This is why celebrity endorsements work so well.

Scarcity – we have a extreme motivation of fear of loss, either or something, or of the opportunity to have something.  Who doesn’t like to keep doors open as long as possible?

The one place the book falls down a little bit is in the sections at the end of each chapter talking about how to resist that particular technique through jujitsu – the art of “turning the enemy’s strength to your advantage.”  While nice in theory, Cialdini’s examples aren’t super helpful beyond saying “when you think you’re getting suckered, stop — and then say no.”

Overally, though, the book is well written and choc full of examples.  Thanks to marketer Mallory Kates for sending me this great book!

How Much Marketing Is Too Much Marketing?

It seems like a busy holiday season is already underway for marketers, and hopefully for the economy, shoppers as well.  Just for kicks, I thought I’d take a rough count of how many marketing messages I was exposed to in a given day.  Here’s what the day looked like:

5:30 a.m. – alarm clock goes off with 1010 WINS news radio in the middle of an ad cycle – 2 ads total.  Nice start to the day.

5:45-6:30 – in the gym, watching Today In New York News on NBC for 30 minutes, approximately 6 ad pods, 6 ads per pod – 36 ads total.  So we’re at 38, and it’s still dark out.

7:00 – walk to subway and take train to work, then walk to office from subway.  Probably see 6 outdoor ads of various kinds on either walk, then about 8 more on the subway within clear eyeshot – 20 ads total.

7:30 – quick scan of My Yahoo – 2 ads total.

7:32 – read Wall St. Journal online, 15 page views, 3 ads per page – 45 ads total.

7:40 – Catch up on RSS feeds and blogs, probably about 100 pages total, only 50% have ads – 50 ads total (plus another 25 during the rest of the day).

7:50 – Sift through email – even forgetting the spam and other crap I delete – 10 ads total (plus another 10 during the rest of the day).

8:00-noon – basically an ad free work zone, but some incidental online page views are generated in the course of work – 25 ads total, plus a ton of Google paid search ads along the way.

Noon-1 p.m. – walk out to get lunch and come back to office, so some outdoor ads along the path – 12 ads total.

1-7 p.m. – same work zone as before – 25 ads total, plus lots of Google.

7 p.m. – walk to Madison Square Garden to see the Knicks get clobbered by Milwaukee, see lots of outdoor ads along the way – 20 ads total.

7:30-9:30 – at the Garden for the Knicks game, bombarded by ads on the scoreboards, courtside, sponsorship announcements, etc.  Approximately 100 ads total (and that’s probably being exceptionally generous).

9:30 – subway ride and walk home – 14 ads total.

10:00 – blitz through episodes of The Daily Show and West Wing in TiVo.  8 minutes of :30 advertising per half hour, or 48 ads total, fortunately can skip most of them with TiVo.

11:00 – flip through issue of The New Yorker before bed – 50 ads total.

Total: 492 ads.

I’m sure I missed some along the way, and to be fair, I am counting the ads I skipped with TiVo — but hey, I’m also not counting all the ads I saw on Google, so those two should wash each other out.  On the other hand, if I drove to and from work in California, I’d have seen an extra 100 billboards, and if I read the New York Times print edition, I’d have seen an extra 100 print ads.

Approximate cost paid to reach me as a consumer today (assuming an average CPM of $10): just under $5.  Sanity check on that — $5/day*200 million Americans who are “ad seers”*365 days is a $365 billion advertising industry, which is probably in the right ballpark.

What are the two ads I consciously acted on?  An offer from LL Bean through email (I’m on their list) for a new fleece I’ve been meaning to get, and a click on one of the Google paid search results.  No doubt, I subconsciously logged some good feelings or future purchase intentions for any number of the other ads.  Or at least so hope all of the advertisers who tried to reach me.

What’s the message here?  A very Seth Godin-like one.  Nearly all of the marketing thrown at me during the day (Seth would call it interrupt marketing) — on the subway, at the Garden, on the sidebar of web pages — is just noise to me.  The ones I paid attention to were the ones I WANTED to see:  the email newsletter I signed up for from a merchant I know and love; and a relevant ad that came up when I did a search on Google.

Brand advertising certainly has a role in life, but permission and relevance rule the day for marketers.  Always.

Book Short:  Underdog Victorious

The Underdog Advantage, by David Morey and Scott Miller, was a worthwhile read, though not a great book.  It was a little shallow, and although I enjoyed its case studies (who doesn’t love hearing about Ben & Jerry’s, Southwest, JetBlue, Starbucks?), I didn’t feel like the authors did enough to tie the details of the success of the case study companies back to the points they made in the book.

That said, the book had some great reminders in it for companies of all sizes and stages.  The main point was that successful companies always think of themselves as the underdog, the insurgent, and never get complacent.  They run themselves like a political campaign, needing to win an election every single day.  A lot of the tactics suggested are timeless and good to remember…things like never declare victory, always play offense, always respond to attacks, remember to communicate from the inside out, and remember to sell employees on a mision and purpose in order to make them your main ambassadors.  The laundry list of tactics is the book’s greatest strength.