Context
I wrote a post in 2013 entitled Debunking the Myth of Hiring for Domain Expertise vs. Functional Expertise. In it, I talk about how in hiring senior executives, sometimes you can’t get both functional expertise (great Head of X) and great domain expertise (subject matter expert in X), but that in scaling businesses, there’s another important vector to consider, which is that if your principal business challenge is scaling, then a critical thing to look for in a potential executive is experience with scaling businesses, or at least experience working at businesses of different sizes/stages.
Today’s post is about a fourth vector beyond functional expertise, domain expertise, and scaling expertise: Context, an important vector to consider as well. When I first had this thought, I was having trouble distinguishing it from domain expertise. Now a few months later, I think I am clear on the distinction.
I worked for a while as an interim executive at a company that had giant companies for clients – very, very large companies. Tens and Hundreds of Thousands of employees. And the scope of services we provided was very internal to our clients, meaning our services touch 100% of employees. Early in my career, I worked as a management consultant and did spend the bulk of two years working in very large companies, frequently onsite for several months at a time. Most of my career, though, I have worked in startups/small companies, and while the clients I’ve worked with often included some very large companies, we’ve typically served very small, externally-oriented teams at large companies. So my personal context for this job is somewhat limited.
Why is that relevant? It’s different to work in a small, well lit, high energy, open plan, newly designed urban office than it is to work in a massive footprint office filled with high-wall cubicles and no windows in a suburban office park. It’s different to work in an environment where there are 5+ layers of management between someone and a department head. It’s different to work in a place where career paths are largely vertical (or involve switching business units) as opposed to what I’m used to, which is careers that can Scale Horizontally. And on and on. All these things are important Context for how our clients consume our services. And they’re all different from what I’m used to.
There is no substitute for actually working years on end in large companies, just as there is no substitute for working years in the startup context. Having said that, I think context can be learned about as quickly as subject matter, and about at the same depth.
Grit
I was honored this week to be in a small group “fireside chat” with Angela Duckworth, author of the book Grit: The Power of Passion and Perseverance, and to meet her and ask a question.
I want to hit on one theme here from the book and dialog, but I’ll start by sharing a 2×2 matrix (remember, I’m an ex-consultant, I think in frameworks) that we’ve used at home with our kids periodically. For the most part, we use it to talk to them about why they should work harder on math homework, but it’s had other use cases as well. Hopefully it makes sense on the face of it…

…but essentially the framework teaches that if you are talented AND work hard at something, you can achieve great things. If you have talent and slack off, you can get by perfectly fine. If you have no talent but work your butt off, you can get there…but it’s hard. And if there’s an area of life where you have no talent and don’t work at it, so be it, but you’re punting on that whole thing.
In the book, Duckworth takes this to a whole new level by adding a simultaneous second equation:
- Talent x Effort = Skill
- Skill x Effort = Achievement
This makes the statement that “your first bit of talent, combined with effort increases your skill level. Your increasing skill, multiplied by effort, leads to achievement. That means effort counts twice. Once for skill and once for achievement. But that doesn’t mean it’s twice as important. If you substitute the skill equation into the achievement equation, you end up with
- Talent x Effort x Effort = Achievement, which means that
- Talent x Effort² = Achievement.
Or in other words, “Your effort is exponentially more important than how talented you are.”
All I have to say is that while I won’t create a second graphical explanation of this and probably won’t go back and amend my 2×2 for my kids, I think Duckworth is right, with one caveat. If you don’t have a certain baseline of talent in a certain area, it just doesn’t matter how much effort you apply – your achievement has some kind of natural governor to it. When I was a kid, I would dearly have loved to be the shortstop for the San Diego Padres, but between being a lefty, a kid, and not what you would call overly athletic, it wouldn’t have mattered if I spent every waking hour of a decade working at it…I never would have gotten there. Having said that, those cases may be edge cases, and again, I find that the emphasis on effort on top of my framework is a very worth application.
But go read Grit. It’s much better and more detailed than this blog post!
What Job is Your Customer Hiring You to Do?
My friend George, one of our co-founders at Return Path (according to him, the best looking of the three), has a wonderful and simple framing question for thinking about product strategy: what job is your customer hiring you to do? No matter what I’m working on, I am finding George’s wisdom as relevant as ever, maybe even more so since I am still learning the new context.
Why is this a useful question to ask? It seems really simple – maybe even too simple to drive strategy, doesn’t it?
It’s very easy in technology and content businesses (maybe other spaces too) to get caught up in a landslide of features and topics. In a dynamic world of competition and feature parity, product roadmaps can easily get cluttered. They can also get cluttered by product teams who have their own view of what should be the next feature, module, or content widget. Sometimes looking at product usage data is helpful, but sometimes it produces more noise than signal because it can easily miss the “why” or change day to day.
And once a product is mature, it can be very difficult to understand which of its many elements — even if they are all used — are the ones truly driving the most value for customers. It’s easy to assume it’s the newest, the slickest, the ones that are generating the most buzz. It’s even easier to assume that when it comes to content. But sometimes it’s now. Sometimes it’s the legacy part of the product. Sometimes it’s a small side feature you don’t focus on. Sometimes it’s something you used to do but don’t really do any more!
By asking customers the simple question — what are you hiring us to do for you? — you can start to get to the heart of the matter, the heart of what your strategy should be. Peeling the onion once you understand that and getting into the specifics of the different tasks or jobs your customer does that derive from your main point of value, as George would say, “jobs to be done,” is much more straightforward. When defining a Job to Be Done:
- Focus on a functional job (not an emotional one, e.g, “I need to look smart to the boss”)
- Try to ensure that you are looking at the whole job, not just a piece of the job. It’s easy to get too narrow in your definition
- Make sure it is the customer’s definition of the job, not yours
There’s always a role and a need for innovative product owners to help define a space, define value, demonstrate it for customers. This framework is meant to be additive to a high functioning product owner’s job, it can never replace it.
(As a small post-script, Friday December 6 marks 20 years since we started Return Path…a fitting day to post a bit of a tribute to George!)
Book Short – You’re in Charge – Now What?
Thanks to my friend and long-time former Board member Jeff Epstein, I recently downed a new book, You’re in Charge – Now What?, by Thomas Neff and James Citrin. I’m glad I read it. But it was one of those business books that probably should have just been a Harvard Business Review article. It’s best skimmed, with helpful short summaries at the end of every chapter that you could blow through quickly instead of hanging on every word.
The authors’ 8-step plan is laid out as:
- Prepare yourself during the countdown
- Align expectations
- Shape your management team
- Craft your strategic agenda
- Start transforming culture
- Manage your board/boss
- Communicate
- Avoid common pitfalls
Ok fine, those make sense on the surface. Here are three things that really stood out for me from the book:
First, “working” before you’re officially working – the countdown period. I tried hard NOT to do this when I was between things, but I’m glad I did the things I did, and now, I wish I had done more. The most poignant phrase in the book is “scarce time available during your first hundred days.” That is an understatement. As my “to read” pile grows and grows and grows with no end in sight…I wish I had done more pre-work.
Second, remember that in every interaction, you are being evaluated as much as you are evaluating. And note that for many people, they will be thinking very critically, things like “do I want to work with this person…is he/she showing signs that he/she wants to work with me?” Yes, we all know as leaders, we live in a fishbowl. But I think that may be even more true during the first couple months on the job.
Finally, this phrase stood out for me: “Acknowledging and in some cases embracing your predecessor can sustain a sense of continuity within the organization and instill a sense of connectivity with employees’ shared past.” There is frequently a temptation to focus on things that need change, which invariably there are…and which invariably you will hear from people who are happy to find a willing new ear to listen to them. But this posture of acknowledge/embrace is especially true in my case, where my predecessor is the founder and 25-year CEO who continues on as our active chairman.
I know there are a ton of books like this on the market, and while I’ve only read this one, I’d say that if you’re starting a new CEO or executive-level job, this is a good one to at least skim to get some ideas.
The Nachos Don’t Have Enough Beef in Them!
(This is an excerpt from Chapter 23 of Startup CEO, “Collecting Data,” in which I write about the importance of observing and learning from customers and friends of the firm, as well as employees.)
Here’s a story for you that happened 10+ years ago. I’m sitting at the bar of Sam Snead’s Tavern in Port St. Lucie, Florida, having dinner solo while I wait for my friend Karl to arrive. I ask the bartender where he’s from, since he has an accent. Nice conversation about how life is rough in Belfast and thank goodness for the American dream. I ask him what to order for dinner and tell him a couple of menu items I’m contemplating. He says, “I don’t know why they don’t listen to me. I keep telling them that all the people here say that the nachos aren’t good because they don’t have enough beef in them.”
I order something else.
Five minutes later, someone else pounds his hand on the bar and barks out, “Give me a Heineken and a plate of nachos.”
The bartender enters the order into the point-of-sale system.
What’s the lesson? Listen to your front-line employees—in fact, make them your customer research team. I have seen and heard this time and again. Employees deal with unhappy customers, then roll their eyes, knowing full well about all the problems the customers are encountering and also believing that management either knows already or doesn’t care. There’s no reason for this! At a minimum, you should always listen to your customer-facing employees, internalize the feedback and act on it. They hear and see it all. Next best prize: ask them questions. Better yet: get them to actively solicit customer feedback
OnlyOnce, Part XX
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!
Sometimes a Good Loss is Better than a Bad Win
I just said this to a fellow little league coach, and it’s certainly true for baseball. I’ve coached games with sloppy and/or blowout wins in the past. You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game. And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run. You are sad about the L, but at least you left it all out on the field.
Is that statement true in business?
What’s an example of a “bad” win? Let’s say you close a piece of business with a new client…but you did it by telling the client some things that aren’t true about your competition. Your win might not be sustainable, and you’ve put your reputation at risk. Or what about a case where you release a new feature, but you know you’ve taken some shortcuts to launch it on time that will cause downstream support problems? Or you negotiate the highest possible valuation from a new lead investor, only to discover that new lead investor, now on your Board, expects you to triple it in four years and is way out of alignment with the rest of your cap table.
On the other side, what’s an example of a “good” loss? We’ve lost accounts before where the loss was painful, but it taught us something absolutely critical that we needed to fix about our product or service model. Or same goes for getting a “pass” from a desirable investor in a financing round but at least understanding why and getting a key to fixing something problematic about your business model or management team.
What it comes down to is that both examples – little league and business – have humans at the center. And while most humans do value winning and success, they are also intrinsically motivated by other things like happiness, growth, and truth. So yes, even in business, sometimes a good loss is better than a bad win.
How to Get Laid Off
How to Get Laid Off – an Employee’s Perspective
One of my colleagues at Return Path saw my post about How to Quit Your Job about 5 years ago and was inspired to share this story with me. Don’t read anything into this post, team! There is no other meaning behind my posting it at this time, or any time, other than thinking it’s a very good way of approaching a very difficult situation, especially coming from an employee.
In 2009 I was working at a software security start up in the Silicon Valley. Times were exceedingly tough, there were several rounds of layoffs that year, and in May I was finally on the list. I was informed on a Tuesday that my last day was that Friday. It was a horrible time to be without a job (and benefits), there was almost no hiring at all that year, one of the worst economic down turns on record. While it was a hard message, I knew that it was not personal, I was just caught up on a bad math problem.
After calling home to share the bad news, I went back to my desk and kept working. I had never been laid off and was not sure what to do, but I was pretty sure I would have plenty of free time in the short term, so I set about figuring out how to wrap things up there. Later that day the founder of the company came by, asked why I had not gone home, and I replied that I would be fine with working till the end of the week if he was okay with it. He thanked me.
Later that week, in a meeting where we reviewed and prioritized the projects I was working on, we discussed who would take on the top three that were quite important to the future of the company. A few names were mentioned of who could keep them alive, but they were people who I knew would not focus on them at all. So I suggested they have me continue to work on them, that got an funny look but when he thought about it , it made sense, they could 1099 me one day a week. The next day we set it up. I made more money than I could of on unemployment, but even better I kept my laptop and work email, so I looked employed which paid off later.
That one day later became two days and then three, however, I eventually found other full time work in 2010. Layoffs are hard, but it is not a time to burn bridges. In fact one of the execs of that company is a reference and has offered me other opportunities for employment.
Response to the Journal
(This post is running concurrently on the Return Path blog.)
It is now widely understood that the Internet runs on data. I first blogged about this in 2004—14 years ago!— here. People have come to expect a robust—and free!—online experience. Whether it’s a shopping app or a social media platform like Instagram, these free experiences provide a valuable service. And like most businesses, the companies that provide these experiences need to make money somehow. Consumers are coming to understand and appreciate that the real cost of a “free” internet lies in advertising and data collection.
Today, the Wall Street Journal ran an article exploring the data privacy practices of Google and some of the third party developers who utilize their G Suite ecosystem. Return Path was among the companies mentioned in this article. We worked closely with the journalist on this piece and shared a great deal of information about the inner workings of Return Path, because we feel it’s important to be completely transparent when it comes to matters of privacy. Unfortunately, the reporter was extremely and somewhat carelessly selective in terms of what information he chose to use from us — as well as listing a number of vague sources who claimed to be “in the know” about the inner workings of Return Path. We know that he reached out to dozens of former employees via LinkedIn, for example, many of whom haven’t worked here in years.
While the article does not uncover any wrongdoings on our part (in fact, it does mention that we have first-party relationships with and consent from our consumers), it does raise a larger privacy and security concern against Google for allowing developer access to Gmail’s API to create email apps. The article goes on to explain that computers scan this data, and in some rare cases, the data is reviewed by actual people. The article mentions a specific incident at Return Path where approximately 8,000 emails were manually reviewed for classification. As anyone who knows anything about software knows, humans program software – artificial intelligence comes directly from human intelligence. Any time our engineers or data scientists personally review emails in our panel (which again, is completely consistent with our policies), we take great care to limit who has access to the data, supervise all access to the data, deploying a Virtual Safety Room, where data cannot leave this VSR and all data is destroyed after the work is completed.
I want to reaffirm that Return Path is absolutely committed to data security and consumer data privacy. Since our founding in 1999, we’ve kept consumer choice, permission, and transparency at the center of our business. To this end, we go above and beyond what’s legally required and take abundant care to make sure that:
- Our privacy policy is prominently displayed and written in plain English;
- The user must actively agree to its terms (no pre-checked boxes); and
- A summary of its main points is shown to every user at signup without the need to click a link
While a privacy expert quoted in the article (and someone we’ve known and respected for years) says that he believes consumers would want to know that humans, not only computers, might have access to data, we understand that unfortunately, most consumers don’t pay attention to privacy policies and statements, which is precisely why we developed succinct and plain-English “just-in-time” policies years before GDPR required them. When filling out a form people may not think about the impact that providing the information will have at a later date. Just-in-time notices work by appearing on the individual’s screen at the point where they input personal data, providing a brief message explaining how the information they are about to provide will be used, for example:

It’s disappointing to say the least that the reporter called this a “dirty secret.” It looks pretty much the opposite of a secret to me.
In addition to our own policies and practices, Return Path is deeply involved in ongoing industry work related to privacy. We lead many of these efforts, and maintain long-term trusted relationships with numerous privacy associations. Our business runs on data, and keeping that data secure is our top priority.
Further, I want to address the scare tactics employed by this journalist, and many others, in addressing the topics of data collection, data security, and who has access to data. It’s common these days to see articles that highlight the dangers that can accompany everyday online activities like downloading an app or browsing a retail website. And while consumers certainly have a responsibility to protect themselves through education, it’s also important to understand the importance of data sharing, open ecosystems, and third party developers. And more than that, it’s important to draw distinctions between companies who have direct relationships with and consent from consumers and ones who do not.
While they may not be top of mind, open ecosystems that allow for third-party innovation are an essential part of how the internet functions. Big players like Facebook and Google provide core platforms, but without APIs and independent developers, innovation and usability would be limited to big companies with significant market power and budgets—to the detriment of consumers. Think about it—would Facebook have become as wildly popular without the in-app phenomenon that was Farmville? Probably, but you get the point: third party applications add a new level of value and usefulness that a platform alone can’t provide.
Consumers often fall into the trap of believing that the solution to all of their online worries is to deny access to their data. But the reality is that, if they take steps like opting out of online tracking, the quality of their online experience will deteriorate dramatically. Rather than being served relevant ads and content that relates to their browsing behaviors and online preferences, they’ll see random ads from the highest bidder. Unfortunately some companies take personalization to an extreme, but an online experience devoid of personalization would feel oddly generic to the average consumer.
There’s been a lot of attention in the media lately—and rightfully so—about privacy policies and data privacy practices, specifically as they relate to data collection and access by third parties. The new GDPR regulations in the EU have driven much of this discussion, as has the potential misuse of private information about millions of Facebook users.
One of Return Path’s core values is transparency, including how we collect, access and use data. Our situation and relationship with consumers is different from those of other companies. If anyone has additional questions, please reach out.
Feedback Overload and Confusion – a Guide for Commenting on Employee Surveys
We run a massive employee survey every year or so called The Loop, which is powered by Culture Amp. We are big fans of Culture Amp, as they provide not only a great survey tool but benchmarks of relevant peer companies so our results can be placed in external context as well as internal context.
The survey is anonymous and only really rolled up to large employee groups (big teams, departments, offices, etc.), and we take the results very seriously. Every year we run it, we create an Organization Development Plan out of the results that steers a lot of the work of our Leadership team and People team for the coming year.
I just read every single comment that employees took the time to write out in addition to their checkbox or rating responses. This year, that amounted to over 1,200 verbatim comments. I am struggling to process all of them, for a bunch of reasons you’d expect. Next year we may give employees some examples of comments that are hard to process so they understand what it’s like to read all of them…and we may reduce the number of places where employees can make comments so we try to get only the most important (and more detailed) comments from people to keep the volume a little more manageable.
But I thought it might be useful to give some general advice to people who write comments on anonymous surveys. Your company may have every good intention of following up on every last comment in an employee survey (we do!), but it’s difficult to do so when:
- The comment is not actionable. For example, “The best thing about working at Return Path is…’I can afford to live nearby.'” That doesn’t do much for us!
- The comment is too vague. For example, “I’m not the engineer I was a year ago” – we have no idea what that means. Is it a plus or a minus? What is behind it?
- The comment is likely to be in conflict with other comments and doesn’t give enough detail to help resolve conflicts. 40 positive comments about the lunch program in an office and 40 negative comments about the lunch program in the same office kind of get washed out, but “Lunches are good, but please have more gluten-free options” is super helpful.
- The comment lacks context. When the answer to the question “What would be the one thing we could do right away to make RP a better place to work?” is “Investing in some systems,” that doesn’t give us a starting point for a next step.
- The commenter disqualifies him or herself. Things like “Take everything I’m saying with a grain of salt…I’m just an engineer and have no real idea of what I’m doing” that punctuate a comment are challenging to process.
- The commenter forgets that the comments are anonymous. “I have serious problems with my manager and often think of leaving the company” is a total bummer to hear, but there’s not a lot we can do with it. I hope with something like this that you are also having a discussion with someone on the People team or your manager’s manager!
We’re doing everything employees would expect us to do – reading the ratings and comments, looking at trends over time, breaking them down by office and department, and creating a solid Organizational Development Plan that we’ll present publicly and follow up on…but hopefully this is useful for our company and others in the future as a guide to more actionable commenting in employee surveys.
There’s a word or two missing from the English language
In my personal life, I have acquaintances, I have friends, and I have good/close friends.
In my work life, I have colleagues – the professional equivalent of acquaintances.
But what comes after that professionally? We spend over half our waking life at work. Of course we are going to build important relationships. Some of them will cross over to personal and become legitimate “friends” or “good friends.” I always feel some sense of honor when a colleague introduces me to someone as a true friend.
But for those that don’t cross that chasm – for those who are truly just professional relationships but ones with increasing closeness – what are we supposed to call them?
I guess in a pinch we could call the next level up “work friends,” although that sounds odd and a bit impersonal. But what about the level after that? What is a “work good friend” or even a “good work friend”? Those sound even weirder. And yet, “work good friends” abound! I can probably think of 5 or 10 “work friends” or “work good friends” for every true friend or good friend in the workplace.
Has anyone found a good word or phrase for this yet?



