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

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university.  You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation.  Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years?   Fit matters mostly around values.  It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours.  Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level  Find someone with the right experience set that you can learn from RIGHT NOW.  Or at least this year.  Maybe the person is the right mentor next year, maybe not.  Depends on what you need.  For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm. 

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different.  I got lucky in my selection of a CEO Coach almost 20 years ago.  My board member Fred Wilson told me I needed to work with one, I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my Board better,” and for some reason, he decided to take the assignment.  I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.  

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally.  CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end.  The former can be incredibly helpful — just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions.  The latter can be helpful as well — just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit.  There is no right or wrong universal answer here to what makes someone the right choice for you.  For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.  

Therapy and coaching are different, though.  A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be.  A 1 is going to help you discover and drive to your leadership style.  A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges.  Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s.  A good CEO Coach is someone you can work with literally forever.   

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is.  How do they typically start engagements.  How structured or unstructured are they in their work?  Check references and ask some of their other CEO clients what it’s been like to work with them.  This is all true to a much lesser extent with Mentors.  In both cases, you should probably do a test session or two before signing up for a longer-term engagement.  You wouldn’t buy a car without taking it for a test drive.  This is an even more consequential decision.  

And in both cases, there should be no ego in the process.  You should never feel like you’re being sold by a CEO Coach or CEO Mentor.  And they shouldn’t feel hurt by you picking someone else, either.  Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming:  How to get the most out of working with a CEO Mentor or CEO Coach 

We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.

Episode 1: 3 Tips to Scale Your Culture with Nick Mehta

Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many? Nick and I discussed what happens to company culture when you achieve your scaling and growth goals.

Episode 2: Managing Up with Cristina Miller

Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Cristina Miller—a seasoned, results-driven executive and board member (including on Bolster’s board!) with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.

Episode 3: Common Mistakes Founders Make with Fred Wilson

Fred Wilson has been a venture capitalist since 1987 and has worked with me for over 20 years now—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. Listen to this episode to learn how to recognize and avoid those mistakes for yourself.

Episode 4: Cultivating Talent to Promote Internally with Nick Francis

In this episode, Nick Francis—co-founder and CEO of Help Scout—joins me to discuss what it takes to cultivate in-house talent and embody organizational values. I talk about my playbook for building effective teams and developing leaders with a growth mentality as part of this.

Episode 5: Deep Dive with Jeff Epstein

Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator (and one of my former board members) Jeff Epstein joined me for an extended episode about the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. Tune in to follow the shifts in Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.”

Episode 6: Hallmarks of Successful Founders with David Cohen

David Cohen, Founder and Chairman at Techstars, shares the top three signs he looks for that differentiate successful founders—things that are nearly impossible to fake. Either you have them, or you don’t. This one is awesome.

Episode 7: Success as a Fractional Exec with Courtney Graeber

If you know anything about Bolster, you know we’re a champion for fractional executives. As an Interim Chief People Officer, HR Executive Consultant, and trusted mentor to executive teams, Courtney Graeber provides feedback and recommendations that enhance organizational culture and attract, develop, and retain top talent. Many of her clients are navigating transitional periods—and that’s where Courtney’s expertise comes in. Listen in to learn what it’s like to be (or work with) a fractional head of people.

Episode 8: 3 Ways VCs Say “No” Without Saying “No” with Jenny Fielding

It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says one of NYC’s top pre-seed investors Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either.  Here, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.

Episode 9: Building a Strong Culture with Jailany Thiaw

Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines, joins me to discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.

Episode 10: Deep Dive with Brad Feld

Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur who I’ve also worked with for more than two decades. In this episode, he and I take a deep dive into how startups and venture capital have changed over the past 25 years—and what has stayed the same.  They also discuss the dynamics of startup boards, along with common characteristics that make founders or companies successful at scale.

Episode 11: The Value of Podcasting with Lindsay Tjepkema

This episode is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers.  She and I dive into the reasons why podcasts are such a great way to get your voice—literally—out into the world. Tune in to hear Lindsay’s tips for starting a podcast as a CEO, setting expectations, asking meaningful questions, and creating human connection. We’ve loved partnering with Lindsay and her team so far on The Daily Bolster!

Episode 12: Interviewing for “Culture Fit” with Rory Verrett

What does it mean to interview for culture fit? How should CEOs and leaders go about doing it—and is there a better way? Rory Verrett is the founder and managing partner of Protégé Search, the leading retained search and leadership advisory firm focused on diverse talent, and is also on Bolster’s Board of Directors. He and I discuss why CEOs are not always the best arbiters of company culture, then we dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.

The Daily Bolster is for people in the startup world want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed. Instead, we’re getting straight to the point with mostly 5-minute episodes. Any and all feedback welcome!

This is the second post in the series…. the first one When to hire your first Chief People Officer is here).

While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything illegal, discriminatory, or harassing, you’ll end up in legal trouble and you’ll lose—big time. So, it’s not enough, if you’re expanding rapidly, to “just get a Chief People Officer,” you need to hire a great Chief People Officer and I have found that great Chief People Officers do three things particularly well:

The most important characteristic or attribute of a great Chief People Officer is that they believe their function is strategic. In Startup CXO Chief People Officer Cathy Hawtrey wrote about the ways in which HR/People can be a strategic function and not just a tactical corporate function.  It’s true of most functions, but for whatever reason, (likely past experience), HR leaders frequently don’t view themselves or their functions as strategic, which is not only a huge missed opportunity but maybe says something more important about the confidence level of the Chief People Officer.  If that’s their frame of reference, then they will likely be tactical managers, they’ll keep the trains running on time, but you won’t be able to anticipate the changing talent landscape, much less be strategic about it.  If they believe they can move the needle on the business by improving engagement and productivity and efficiency, if they believe they can make the executive team more effective by helping you with team facilitation and coaching…they can do anything.

A second important characteristic of the Chief People Officer is courage—they have the courage to call you (you, the CEO) out on things directly and firmly when they see you doing or saying anything that is a bit off. It could be around language, inclusion, values, authenticity, or anything else, but they don’t let it slide or ignore it. The CPO, along with you, are the principal stewards of the company’s values and culture.  Even the best CEOs benefit from having a watchdog from time to time.

A third critical trait of a great Chief People Officer is that they think about investment in People in terms of ROI.  It’s one thing to run a killer recruiting function and fill seats efficiently, with high quality, as asked.  It’s an entirely different thing to start the recruiting process by asking if the role is needed, at that level and compensation band, or whether there are other people, fractional people, contractors, or shifts in lower value activities that could be put to work instead.  Only heads of People with deep understandings of the business can transform the function from a gatekeeper/”no” role into a business accelerator.

A great Chief People Officer is all of these things—strategic, courageous, and financially astute. Above all, great Chief people Officers know that they are the role model within a company and that their behavior, their language, their inclusiveness is setting the tone and providing a template for others to follow. 

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

This was a big week for Return Path.  First we announced a $35mm financing led by an exceptional private equity firm that I’d never heard of before the middle of the fundraising process a few months ago.  We are happy to have them join our very strong board and syndicate and even happier to have additional investment capital to accelerate our growth, especially in newer businesses for us like Email Fraud Protection and our overall data and analytic capabilities.

But in some ways even more important, or at least more sentimentally important news this week is that tomorrow, December 6, marks the 15th anniversary of Return Path’s founding.  A decade and a half with probably over 800 employees in total over time in a dozen locations and several thousand clients worldwide.  We’ve “served” over 30 million consumers, including some of our legacy businesses like ECOA, Postmaster Direct, and Authentic Response, as well as our current panel.  Preparing for our annual year-end all-hands meetings over the next couple weeks was a fun exercise this week in pulling up, diving into lessons learned from this past year (and more), and trying to crisply articulate our vision for the next few years.

The next leg of our journey is going to be interesting and quite different from the past in many ways, though of course some things, like our values and spirit, won’t change.  Lots of aspects of our jobs will.  But that’s a good thing.  I’m not sure I could have ever done the same job for 15 years, and even though my title and company haven’t changed since 1999, the substance of my job has changed every few years.  I have loved every minute of every day of this journey (even the not-so-good ones) and am privileged to work with such an amazingly talented executive team, staff, and board.  I won’t say “here’s to the next 15,” because I can’t count that high, but here’s to Return Path!

And to celebrate #15, my colleague Tom Sather assembled this fun infographic that has some fun stats and is a bit of walk through history.

The Best Place to Work, Part 7: Create a Thankful Atmosphere

My final installment of this long series on Creating the best place to work (no hierarchy intended by the order) is about Creating a thankful atmosphere.

What does creating a thankful atmosphere get you?  It gets you great work, in the form of people doing their all to get the job done.  We humans – all of us, absolutely including CEOs – appreciate being recognized when they do good work.  Honestly, I love what I do and would do it without any feedback, but nothing resonates with me more than a moment of thanks from someone on my exec team or my Board.  Why should anyone else in the organization be any different?

This is not about giving everyone a nod in all-hands by doing shout-outs.  That’s not sustainable as the company grows.  And not everyone does great work every week or month!  And it’s not about remembering to thank people in staff meetings, either, although that’s never bad and easier to contain and equalize.

It is about informal, regular pats on the back.  To some extent inspired by the great Ken Blanchard book Whale Done, and as I’ve written about before here, it’s about enabling the organization to be thankful, and optimizing your own thankfulness.

Years ago we created a peer award system on our company Intranet/Wiki at Return Path.  We enable Peer Recognition through this.  As of late, with about 350 employees, we probably have 30-40 of these every week.  They typically carry a $25 gift card award, although most employees tell me that they don’t care about the gift card as much as the public recognition.  Anyone can nominate anyone for one of the following awards, which are unique to us and relevant to our culture:

• EE (Everyday Excellence) -is designed for us to recognize those who demonstrate excellence and pride in their daily work.
• ABCD (Above and Beyond the Call of Duty) -is designed for us to recognize the outstanding work of our colleagues who go Above and Beyond their duties and exemplify exactly what Return Path is about
• WOOT (Working Out Of Title) -is designed for us to recognize those who offer assistance that is not part of their job responsibilities.
• OTB (On The Business)-is about pulling ourselves out of day-to-day tasks and ensuring we are continually aligned with the long-term, strategic direction of the business.  We make sure we’re not just optimizing our current tasks and processes but that we’re also thinking about whether or not we should even be doing those things.  We stop to think outside of the “box” and about the interrelationship between what we are doing and everything else in the organization.  In doing so, we connect the leaves, the branches, the trunk, the roots and soil of the tree to the hundreds of other trees in the forest.  We step back to look at the big picture
• TLAO ( Think Like An Owner)-means that every one of us holds a piece of the Company’s future and is empowered to use good judgment and act on behalf of Return Path.  In our day-to-day jobs we take personal responsibility for our products, services and interactions.  We spend like it’s our own money and we think ahead.  We are trusted to handle situations like we own the business because we are smart people who do the right thing.  We notice the things happening around us that aren’t in our day-to-day and take action as needed even if we’re not directly responsible
• Blue Light Special  is designed for us to recognize anyone who comes up with a clever way to save the company money)
• Coy Joy Award is in memory of Jen Coy who was positive, optimistic and able to persevere through the most difficult of circumstances.  This award is designed to recognize individuals who exemplify the RP values and spread joy through the workplace.  This can be by going above and beyond to welcome new employees, by showing a high degree of care and consideration for another person at RP, by being a positive and uplifting influence, and/or making another person laugh-out-loud.
• Human Firewall is awarded if you catch a colleague taking extra care around security or privacy in some way, maybe a suggestion in a meeting, a feature in a product, a suggestion around policy or practice in the office.

In the early days, we read these out each week at All-Hands meetings.  Today at our scale, we announce these awards each week on the Wiki and via email.  And I and other leaders of the business regularly read the awards list to see who is doing what good work and needs to be separately thanked on top of the peer award.

Beyond institutionalizing thanks…in terms of you as an individual person, there are lots of ways to give thanks that are meaningful.  Some are about maximizing Moments of Truth.  Another thing I do from time to time is write handwritten thank you notes to people and mail them to their homes, not to work.  But there are lots of ways to spend the time and mental energy to appreciate individuals in your company in ways that are genuine and will be noticed and appreciated.  To some extent, this paragraph (maybe this whole post) could be labeled “It’s the little things.”

That’s it for this series…again, the final roundup for the full series of Creating the Best Place to Work is here and individual posts are here:

1. Surround yourself with the best and brightest
2. Create an environment of trust
3. Manage yourself very, very well
4. Be the consummate host
5. Be the ultimate enabler
6. Let people be people
7. Create a thankful atmosphere

Anyone have any other techniques I should write about for Creating the Best Place to Work?

Building the Company vs. Building the Business

I was being interviewed recently for a book someone is writing on entrepreneurship, which focused on identifying the elements of my “playbook” for entrepreneurial success at Return Path.  I’m not sure I’ve ever had a full playbook, though I’ve certainly documented pieces of it in this blog over the years.  One of the conversations we had in the interview was around the topic of building the company vs. building the business.

The classic entrepreneur builds the business — quite frankly, he or she probably just builds the product for a long time first, then the business.  In the course of the interview, I realized that I’ve spent at least as much energy over the years building the company concurrently with the product/business.  In fact, in many ways, I probably spent more time building the company in the early years than the business warranted given its size and stage.  This is probably related to my theme from a few months ago about building Return Path “Backwards.”

What do I mean by building the company as opposed to building the business?

• Building the business means obsessing over things like product features, getting traction with early clients, competition, and generating buzz
• Building the company means obsessing over things like HR policies, company values and culture, long-term strategy, and investor reporting

In the early years, I did some things that now seem crazy for a brand new, 25-person company, like designing a sabbatical policy that wouldn’t kick in until an employee’s 7th anniversary.  But I don’t regret doing them, and I don’t think they were wasted effort in the long run, even if they were a little wasted in the short run.  I think working on company-building early on paid benefits in two ways for us:

1. They helped lay the groundwork for scaling – what we’re finding now as we are trying to rapidly scale up the business, and even over the last few years since we’ve been scaling at a moderate pace, is that we are doing so on a very solid foundation
2. The company didn’t die when the product and business died – because we had built a good company, when our original ECOA business basically proved to be a loser back in 2002, it was a fairly obvious decision (on the part of both the management team and the venture syndicate) to keep the business going but pivot the business, more than once

Starting about four years ago, for the first time, I felt like we had a great business to match our great company.  Now that those two things are in sync, we are zooming forward at an amazing pace, and we’re doing it perhaps more gracefully than we would be doing it if we hadn’t focused on building the company along the way.

I’m not saying that there’s a right path or a wrong path here when you compare business building with company building, although as I wrote this post, my #2 conclusion above is a particularly poignant one, that without a strong company, we wouldn’t be here 12 years later.  Of course, you could always argue that if I’d spent more time building the business and less time building the company, we might have succeeded sooner.  In the end, a good CEO and management team must be concerned about getting both elements right if they want to build an enduring stand-alone company.

If you’ve been reading this blog for a long time (amazingly, it is over 16 years old now!), you know that my company and main professional life’s work up to this point, Return Path, was a 1999 vintage email technology company that we sold last year.  I then had a couple other interim leadership roles, first as interim CEO of another tech company in New York, then in March as the founder and interim leader of Colorado’s COVID-19 Innovation Response Team, which I wrote a series of blog posts about (this is the final post in the series, which links to the whole series).

I’ve generally been quiet on OnlyOnce since last year, but I will be picking up the pace of writing in the weeks ahead for a couple of reasons.

First, I’ve teamed up with a few former Return Path colleagues and some amazing investors and partners to start a new company.  We’re still in quasi-stealth mode, so I’m sorry I can’t talk about it much yet, but I will as soon as we publicly launch sometime after Labor Day.  It’s a cool business in a totally different space from Return Path and plays to our team’s interests and skills around people, values, culture, leadership development, and team scalability. I won’t rename this blog OnlyTwice, but there’s definitely a lot to be said for being a second-time founder.

Related to that, I have also been working on a Second Edition to my book from 2013, Startup CEO: A Field Guide to Scaling Up Your Business, which is coming out in a week or two from Wiley & Sons, and which is available for pre-order now.  I will write a series of posts in the coming weeks that talk about the new material in the second edition.  Our team at the new company is also working on a sequel to that book – more to come on that as well.

For now, I am doing great, enjoying life as a brand new Startup CEO once again, and feeling quite privileged and a little guilty for it by being in this weird bubble of my nice home and yard and feeling safely isolated from the pandemic, from economic dislocation, from social protests, and from having to lead a scaled organization through all of that turmoil.

Why Email Stamps Are a Bad Idea

(also posted on the Return Path blog)

Rich Gingras, CEO of Goodmail is an incredibly smart and stand-up professional.  I’ve always liked him personally and had a tremendous amount of respect for him.  However, the introduction of the email stamp model by Goodmail is a radical departure from the current email ecosystem, and while I’m all for change and believe the spam problem is still real, I don’t think stamps are the answer.  Rich has laid out some of his arguments here in the DMNews blog, so I’ll respond to those arguments as well as add some others in this posting.  I will also comment on the DMNews blog site itself, but this posting will be more comprehensive and will include everything that’s in the other posting.

It seems that Goodmail’s main argument in favor of stamps is that whitelists don’t work.  While he clearly does understand ISPs (he used to work at one), he doesn’t seem to understand the world of publishers and marketers.  His solution is fundamentally hostile to the way they do business.  I’m happy to have a constructive debate with him about the relative merits of different approaches to solving the false positive problem for mailers and then let the market be the ultimate judge, as it should be.

First, whitelists are in fact working.  I know — Return Path runs one called Bonded Sender.  We have documented several places that Bonded Senders have a 21% lift on their inbox delivery rates over non-Bonded Senders.  It’s hard to see how that translates into “bad for senders” as Rich asserts.  When the average inbox deliverability rate is in the 70s, and a whitelist — or, by the way, organic improvements to reputation — can move the needle up to the 90s, isn’t that good?

Second, why, as Goodmail asserts, should marketers pay ISPs for spam-fighting costs?  Consumers pay for the email boxes with dollars (at AOL) or with ads (at Google/Yahoo/Hotmail).  Good marketers have permission to mail their customers.  Why should they have to pay the freight to keep the bad guys away?  And for that matter, why is the cost “necessary?”  What about those who can’t afford it?  We’ve always allowed non-profits and educational institutions to use Bonded Sender at no cost.  But beyond that, one thing that’s really problematic for mailers about the Goodmail stamp model is that different for-profit mailers have radically different costs and values per email they send.

For example, maybe a retailer generates an average of $0.10 per email based on sales and proit.  So the economics of a $0.003 Goodmail stamp would work.  However, they’re only paying $0.001 to deliver that email, and now Goodmail is asserting that they “only” need to pay $0.003 for the stamp.  But what about publishers who only generate a token amount per individual email to someone who receives a daily newsletter based on serving a single ad banner?  What’s their value per email?  Probably closer to $0.005 at most.  Stamps sound like they’re going to cost $0.003.  It’s hard to see how that model will work for content delivery — and content delivery is one of the best and highest uses of permission-based email.

Next, Rich’s assertion that IP-based whitelists are bad for ISPs and consumers because IP-based solutions have inherent technology flaws that allow senders to behave badly doesn’t make sense.  A cryptographically based solution is certainly more sophisticated technology — I’ve never doubted that.

In terms of the practical application, though, I’m not sure there’s a huge difference.  Either type of system (IP or crypto) can be breached, either one is trackable, and either one can shut a mailer out of the system immediately — the only difference is that one form of breach would be trackable at the individual email level and the other would only be trackable in terms of the pipeline or IP.  I’m not sure either one is more likely to be breached than the other — a malicious or errant spammy email can either be digitally signed or not, and an IP address can’t be hijacked or spoofed much like a digital signature can’t be spoofed.

It’s a little bit like saying your house in the suburbs is more secure with a moat and barbed wire fence around it than with locks on the doors and an alarm system.  It’s an accurate statement, but who cares?

I’m not saying that Return Path will never consider cryptographic-based solutions.  We absolutely will consider them, and there are some things around Domain Keys (DKIM) that are particularly appealing as a broad-based standard.  But the notion that ONLY a cryptographic solution works is silly, and the development of a proprietary technology for authentication and crypotgraphy when the rest of the world is trying desparately to standardize around open source solutions like DKIM is an understandable business strategy, but disappointing to everyone else who is trying to cooperate on standards for the good of the industry.  I won’t even get into the costs and time and difficulty that mailers and ISPs alike will have to incur to implement the Goodmail stamp system, which are real.  Now mailers are being told they need to implement Sender ID or SPF as an IP-based authentication protocol — and DKIM as a crypto-based protocol — and also Goodmail as a different, competing crypto-based protocol.  Oy vey!

Email stamps also do feel like they put the world on a slippery slope towards paid spam — towards saying that money matters more than reputation.  I’m very pleased to hear Goodmail clarify in the last couple of days that they are now considering implementing reputation standards around who qualifies for certified mail as well, since that wasn’t their original model.  That bodes well for their program and certainly removes the appearance of being a paid spam model.  However, I have heard some of the proposed standards that Goodmail is planning on using in industry groups, and the standards seem to be much looser than AOL’s current standards, which, if true, is incredibly disappointing to say the least.

Jupiter analyst David Daniels also makes a good point, which is that stamps do cost money, and money on the line will force mailers to be more cautious about “overmailing” their consumers.  But that brings me to my final point about organic deliverability.  The mailers who have the best reputations get delivered through most filtering systems.  Reputations are based largely on consumer complaints and unknown user rates.  So the mailers who do the best job of keeping their lists clean (not overmailing) and only sending out relevant, requested mail (not overmailing) are the ones that will naturally rise to the top in the world of organic deliverability.  The stamp model can claim one more forcing function here, but it’s only an incremental step beyond the forcing function of “fear of being filtered” and not worth the difficulty of adopting it, or the costs, or the risks associated with it.

Rich, I hope to continue to dialog with you, and as noted in my prior posting, I think separating the issues here is healthy.

Fig Wasp #879

I have 7 categories of books in my somewhat regular reading rotation:  Business (the only one I usually blog about), American History with a focus on the founding period, Humor, Fiction with a focus on trash, Classics I’ve Missed, Architecture and Urban Planning (my major), and Evolutionary Biology.  I’m sure that statement says a lot about me, though I am happy to not figure it out until later in life.  Anyway, I just finished another fascinating Richard Dawkins book about evolution, and while I usually don’t blog about non-business books, this one had an incredibly rich metaphor with several business lessons stemming from it, plus, evolution is running rampant in our household this week, so I figured, what the heck?

The Dawkins books I’ve read are The Selfish Gene (the shortest, most succinct, and best one to start with), The Blind Watchmaker (more detail than the first), Climbing Mount Improbable (more detail than the second, including a fascinating explanation of how the eye evolved “in an evolutionary instant”), The Ancestor’s Tale (very different style – and a great journey back in time to see each fork in the evolutionary road on the journey from bacteria to humanity), and The God Delusion (a very different book expounding on Dawkins’ theory of atheism).  All are great and fairly easy to read, given the topic.  I’d start with either The Selfish Gene or maybe The Ancestor’s Tale if you’re interested in taking him for a spin.

So on to the tale of Fig Wasp #879, from this week’s read, Climbing Mount Improbable.  Here’s the thing.  There are over 900 kinds of fig trees in the world.  Who knew?  I was dimly aware there was such a thing as a fig tree, although quite frankly I’m most familiar with the fig in its Newton format.  Some species reproduce wildly inefficiently — like wild grasses, whose pollen get spread through the air, and with a lot of luck, 1 in 1 billion (with a “b”) land in the right place at the right time to propagate.  At the opposite end of the spectrum stands the fig tree.  Not only do fig trees reproduce by relying on the collaboration of fig wasps to transport their pollen from one to the next, but it turns out that not only are there over 900 different kinds of fig trees on earth, there are over 900 different kinds of fig wasps — one per tree species.  The two have evolved together over thousands of millenia, and while we humans might take the callous and uninformed view that a fig tree is a fig tree, clearly the fig wasps have figured out how to swiftly and instinctively differentiate one speices from another.

So what the heck does this have to do with business?  Three quick lessons come mind.  I’m sure there are scores more.

1. Collboration only works when each party benefits selfishly from it.  Fig wasps don’t cross-pollenate fig trees bcause the fig trees ask nicely or will fire them if they don’t.  They do their job because their job is independently fulfilling.  If they don’t — they probably die of starvation.  They’re just programmed with a very specific type of fig pollen as their primary input and output.  We should all think about collaboration this way at work.  I wrote a series of posts a couple years back on the topic of Collboration Being Hard, and while all the points I make in those posts are valid, I think this one trumps all.  Quite frankly, it calls on the core principle from the Harvard Project on Negotiation, which is that collaboration requires a rethinking of the pie, so that you can expand the pie.  That’s what the fig trees and fig wasps have done, unwittingly.  Each one gets what it needs far more so than if it had ever consulted directly with the other.  The lesson:  Be selfish, but do it in a way that benefits your company.

2. Incredibly similar companies can have incredibly distinct cultures.  900+ types of fig tree, each one attracting one and only one type of fig wasp.  Could there be anything less obvious to the untrained human eye?  I assume that not only would most of us not be able to discern one tree or wasp type from another, but that we wouldn’t be able to disdcern discern any of the 900+ types of trees or wasps from thousands or hundreds of thousands or millions (in the case or urbanites) types of trees or bugs in general!  But here’s the thing.  I know hundreds of internet companies.  Heck, I know dozens of email companies.  And I can tell you within 5 minutes of walking around the place or meeting an executive which ones I’d be able to work for, and which ones I wouldn’t.  And the older/bigger the company, the more distinct and deeply rooted its culture becomes.  The lessons:  don’t go to work for a company where you’d even remotely uncomfortable in the interview environment; cultivate your company’s culture with same level of care and attention to detail that you would your family — regardless of your role or level in the company!

3. Leadership is irrelevant when the operating system is tight.  You think fig wasps have a CEO?  Or a division president who reports into the CEO that oversees both fig wasps and fig trees, making sure they all cross-pollenate before the end of the quarter?  Bah.  While as a CEO, you may be the most important person in the organization sometimes, or in some ways, I can easily construct the argument that you’re the least important person in the shop as well.  If you do your job and create an organization where everyone knows the mission, the agenda, the goal, the values, the BHAG, whatever you want to call it — withoutit needing to be spelled out every day — you’ve done your job, because you’ve made a company where people rock ‘n’ roll all night and every day without you needing to be in the middle of what they’re doing. 

I’m sure there are other business lessons from evolutionary biology…send them along if you have good thoughts to share!

No Recession at Return Path

I know, I know.  I shouldn’t jinx us.  But we’re growing like mad at the moment, so much so that we have well almost 50 open positions now across all divisions of the company.  If you want to come join one of the fastest growing, most innovative, and just plain coolest places to work in the industry, we’d love to talk to you.

What’s driving the growth? 

• All our operating units have open positions.  Sender Score (deliverability/whitelisting) has the most openings and is growing explosively.  But Authentic Response (market research) and Postmaster (lead generation) both have openings as well
• Geographic expansion.  We have a bunch of openings in Europe as well as in the U.S.  Other parts of the world…stay tuned for later in the year (or let us know now that you are interested once we get to your corner of the globe)
• The power of email.  Parts of the economy may be a bit choppy now, but online marketing, and email in particular, are going strong.  Clients are finding the e-channels to be more and more effective and efficient ways of driving sales and customer loyalty

Visit the careers page at our web site to have a look — all the new jobs probably aren’t posted yet, but many are, and the rest are on the way shortly.  This is a fun and exciting and rewarding place to work.  Trust me.  I’m completely unbiased.  No, really.  Come join the team, or refer others!

How to Quit Your Job

I sent an email out to ALL at Return Path a few years ago with that as the subject line.  A couple people suggested it would make a good blog post in and of itself.  So here’s the full text of it:

ALL –

This may be one of the weirdest emails you’ll see me (or any CEO write)…but it’s an important message that I want to make sure everyone hears consistently.  If nothing else, the subject line will probably generate a high open rate.  🙂

First off, I hope no one here wants to leave Return Path.  I am realistic enough to know that’s not possible, but as you know, employee engagement, retention, and growth & development are incredibly important to us.

But alas, there will be times when for whatever reason, some of you may decide it’s time to move on.  I have always maintained that there’s more than a Right Way and a Wrong Way to leave a job.  For me, there’s a Return Path Way.

I suppose the Right Way is the standard out there in the world of two weeks’ notice and an orderly documentation and transition of responsibilities.  The Wrong Way is anything less.

So what’s the Return Path Way?

It starts with open dialog.  If you are contemplating looking around for something else, you should let someone know at the thinking stage.  Ideally that would be your manager, but if you’re not comfortable starting the conversation there, find someone else — your department head, someone in HR, me.  Let someone who is in a position to do something about it know that you’re considering other options and why.  The worst thing that will happen is that the company isn’t able to come up with a solution to whatever issues you have.  I PROMISE you that no one here in any management position will ever think less of you or treat you differently or serve up any kind of retribution for this kind of conversation.

After the open dialog and any next steps that come out of it, if you are still convinced that leaving is the right thing for you, tell your manager and whoever you spoke to at the beginning of your search process, not at the end of it.  That hopefully gives the company enough lead time to find a replacement and provide for enough overlap between you and the new hire so that you can train your replacement and hand things off.

Why do we feel so strongly about this?

We invest heavily in our people.  I know we’re not perfect — no company is — but we do our best to take good care with everyone who works here.  Hopefully you know that.  And hiring great people is difficult, as you also know.  Losing a well trained employee is VERY PAINFUL for the company.  It slows our momentum and causes at least a minor level of chaos in the system.  And as shareholders or future shareholders (even if you leave – you can exercise your vested stock options), I’d hope that’s something none of you want to do.

I realize the Return Path Way that I am outlining here is unconventional (and potentially uncomfortable).  But Return Path is an unconventional place to work in a lot of ways.

As I said up front, I hope none of you wants to leave…but if you do, please take this request and advice to heart.

Thank you!

-Matt

Now…I sent this out when the company was a lot smaller, when losing a single employee was losing a real percentage of our workforce!  But I stand by every word in the email, even at a larger size.  This kind of dialog is, as I note in the email, both unconventional and uncomfortable.  But just as one of my management mantras here is “no one should ever be surprised to be fired,” another is “we should never be surprised when someone resigns.”  Ultimately, it’s up to each individual manager to set the right tone with his or her team, and also be in tune enough with each of his or her team members, to foster this.