Several years ago, I blogged about the training program we created for entry-level employees at Return Path, including an embedded presentation that we used to use (which I hope still works on the blog after all these years).

My brother Michael, who is an experienced manager and leader in the digital marketing space, recently sent me this email that I thought I’d share along the same lines to colleagues who are new to the working world. Enjoy!

I signed up to give advice on LinkedIn, and had someone just starting her first job reach out to me asking for general advice. I came up with the attached, and thought it might make for a good blog post on Only Once. If you decide not to publish it, I’m totally cool with that, but thought I would share it. After all, you’re only a brand new employee once too 🙂

1) Listen as much as possible. One of my mentors was fond of reminding me, “God gave you two ears and one mouth!” You should listen at least twice as much as you talk. Get to know your environment and the people around you. Take notes. Observe as much as possible. Learn how others are able to provide value to the organization. Start to anticipate little things that need to be done, and then do them before your manager asks you to. Then bit by bit, use your creativity to start to develop bigger hypotheses about how you can provide even greater value. 

2) “In business, the best story wins.” That’s another quote from a former manager of mine that I have found to be universally true. People in business respond to many things: numbers, bullet points, graphs and visualizations. But they respond to all of those things better when they are wrapped in stories. A great book you can read about storytelling is not about business at all. It’s called “Story” by Robert McKee, and it’s about screenwriting. Despite its apparent lack of applicability, I assure you it will help you think about characters, goals, antagonists, drama, obstacles, and structure — all the elements that go into a good story. When you can present your hypotheses in the context of a story, about your business, your customers, what you want to achieve, how you will do it, and why it matters, you will build consensus and show leadership. Another great book you can read here, again, not about business at all, is “Sapiens” by Yuval Noah Harari. It really opened my eyes about how so much of human history and behavior is really just based on stories. 

3) Be lean. There is another book you should read, called “The Lean Startup”, by Eric Ries. This one is actually about business :). As you think about your hypotheses, think of them in the context of how you can get to market quickly and inexpensively. How you can easily perform experiments that will test your hypotheses. Some of your experiments will not achieve your desired result, but it’s not a failure if you can learn something that helps you pivot towards success. Learnings enable you to adjust and refine your hypotheses as you try to find more value for your organization. 

4) “Objections are requirements” and a corollary “ask questions, don’t make statements.” These two gems are from that first mentor in item number one. Even if you can tell great stories, and even if you can devise and execute lean experiments that achieve business results or provide validated learnings, sometimes “haters gonna hate.” There will always be inhibitors to your bold ideas, with reasons not to proceed with your experiments. Inertia is part of human nature. But don’t fear! When an inhibitor comes along, the first thing you do is start to ask questions. “Why do you object to x?” “Oh,” they’ll say, “because of y and z.” Then ask another question “So if we can resolve y and z, then can we proceed with x?” Rather than repeating yourself and making more statements, by asking questions you’ve just turned their objections into requirements. That inhibitor no longer has their reasons not to proceed with your bold idea. You’ve turned them from antagonists into allies. This kind of creative problem solving is critical to getting your experiments into market, and building consensus and showing your leadership without alienating anyone. 

5) Ok I know I said four, but this one is optional (albeit important). Have fun! Do not take yourself or your role too seriously. Show your personality. Be yourself. That sort of general approach to work and life will draw people to you. They will be relaxed and comfortable around you. They will look forward to meetings with you. You will be successful if you are a good listener, a creative thinker with bold ideas, a fantastic storyteller, an agile experiment developer, and a leader who can build consensus and drive value. But if you are all those things, and you’re fun to be around? Then you will be unstoppable.

Thank you, Michael, for the contribution!

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around Preparing Your Company for an Exit.  That’s pretty different than Preparing Yourself (last week’s post).  

This chapter really focuses on two things.  One is how to think about who within your company knows about the possible deal, which conversations you keep private and which you have more in public.  I’ll save the details on that one for the book.

But there’s a second topic that’s important as well.  And it’s about due diligence and disclosure schedules.  What fun!  I call it “Begin with the end in mind.”  The advice in this section of the book, which is “get a full and complete due diligence checklist from your lawyer before you start a sale process” is something I wish I had done the day I started the company, not the day I started the sale process. 

Knowing what things buyers will want to see, in what form, and how well organized, would have influenced me and my CFO to be more orderly about corporate records (things like shareholder votes and board minutes) as well as client contracts. It’s not that we were disorganized, but over 20 years we put things in several different places and didn’t always migrate old records to new systems. When it came time to put together due diligence and load things into the data room, it was a lot more complicated than it needed to be.

As you can imagine, we are doing this very differently at our new company.  Even if you aren’t well organized now at your company, put on your to do list some kind of spring cleaning of corporate records.  The earlier you do it, the better. Besides, when you first startup you won’t have a ton of details to keep track of so it ought to be easy to do. As you scale you’ll have systems and processes in place as well as, hopefully, ONE PLACE where you store all this information. The time NOT to do it is when you’re in the middle of a very time consuming sale process and simultaneously trying to run your business.

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around the sale process itself.  There are some interesting things in it — the arc and timeline of a deal, working with and through advisors vs. principals dealing with each other directly, optimizing for different stakeholders, and a wonderful long sidebar by my friends and advisors Brian Andersen and Mark Greenbaum from Luma Partners on how to think strategically about an exit and how buyers think.  It’s probably worth buying the whole book just for that.

But what I want to write about here is coping with a failed deal – something my team and I unfortunately had to do a couple years before we actually sold the company and something I’ve never written about or discussed publicly.

In 2017, we almost sold Return Path.  You hear people talk about that from time to time, and frequently it just means “we had a good offer but decided not to take it.”  But in this case, I meant it.  We had a good offer.  We talked to a couple other potential buyers in the industry and ended up getting a great offer.  From a great buyer.  We decided to pull the trigger.  It was time.  We got through the entire deal process, I mean EVERYTHING.  Diligence was painful, thorough – and completed.  Both sides had signed off on things many times along the way.  Documents were done, lawyers had signed off on them, our Board had signed off on them, they had been posted to DocuSign, and our signatures were in escrow.  The press release was written and scheduled to go out in less than 48 hours.  Our all-hands meeting was scheduled.  The acquirer had already sent us their swag to hand out.  About 80 people out of 400+ employees at the company knew about it.  In the football analogy, we weren’t inside the red zone.  We were on the 1-yard line.  

Then the call came.  “I can’t believe we have to tell you this, but our CEO just decided to pull the plug on this at the last minute.”  Buh.  Bye.  To say this was a disappointment is the understatement of a career.  

That evening, I was staying over at a friend’s apartment in Manhattan while Mariquita and the kids were away at the beach with her parents.  After the call came in, I grabbed the two other execs who were still in the office, and we went immediately to a bar.  That calmed me down a little bit.  Then I wandered through Central Park up to the apartment and spent about 4 hours on the phone in a series of cathartic phone calls with the rest of the executive team, some of my closest friends and advisors, and Board members.  

The next couple of days were awful.  We had to tell a huge number of employees “Uh sorry, just kidding.  You know all those stock options that were just about to turn into cash?  Sorry.  The new company we were all excited to join?  Psych!”  The worst part was scrambling to turn the already-scheduled all-hands meeting to announce the deal into just another quarterly update.  Everyone in the room for that meeting who knew about the failed deal just looked at each other with disbelief. We were still in shock.

Eventually of course, we bounced back.  I am now an even more ardent believer in the expression, “What doesn’t kill you makes you stronger.”  The company ended up recovering from this and doing a number of things to make us even better in the years that followed, leading to our eventual sale.  But I will say, it was just terrible, and nothing about the recovery was easy.  I talk about some of the specific steps we took in the book.  But mostly, I hope no one ever has to go through anything like this again.  This was too big, too close to the end, and too well known.  Our team will have deep scar tissue from it for a long time.

Call Me

A fine song by Blondie from 1980 and from the soundtrack of the movie American Gigolo.  And also something that reminded me about the importance of not relying too much on email this past month. 

 I had surgery on my left wrist in early March to hopefully fix a nagging tendonitis problem.  And while I could still write and type post-op, I got sore pretty quickly every day, so I tried to keep those activities to a minimum.  As you might imaging, I do an awful lot of email and IM in my line of work.  So what was my short response to a huge number of emails and IMs for a few weeks?  “Call me.”

 My communications, especially with remote employees, not only didn’t suffer while I couldn’t type a lot – they were stronger than ever.  Even short, two-minute phone conversations – the remote equivalent of someone sticking their head in my office – are preferable to IM or email in many cases.  There’s nothing like the sound of someone’s voice to add real texture to a dialog and to avoid misunderstandings.

Why CEOs Shouldn’t Mess with Engineers

I went to the Vasa Royal Warship Museum in Stockholm the other day, which was amazing – it had a breathtakingly massive 17^th century wooden warship, which had been submerged for over 300 years, nearly intact as its centerpiece.  It’s worth a visit if you’re ever there.

The sad story of its sinking seems to have several potential causes, but one is noteworthy both in terms of engineering and leadership.  The ship set sail in 1628 as the pride of the Swedish navy during a war with Poland.  It was the pride of King Gustavus Adolphus II, who took a keen personal interest in it.  But the ship sank literally minutes after setting sail.

How could that be?  While the king was quick to blame the architect and shipbuilder, later forensics proved both to be mostly blameless.

Likely cause #1:  after the ship was designed and construction was under way, the King overruled the engineers and added much heavier cannons on the upper armament deck.  The ship became top-heavy and much less stable as a result, and while the engineers tried to compensate with more ballast below, it wasn’t enough.

Likely cause #2:  the King cut short the captain’s usual stability testing routines because he wanted to get the ship sailing towards the enemy sooner.

Let’s translate these two causes of failure into Internet-speak.  #1:  In the middle of product development, CEO rewrites the specs (no doubt verbally), overruling the product managers and the engineers, and forces mid-stream changes in code architecture.  #2:  In order to get to market sooner, the CEO orders short-cuts on QA.  I’m sure you’ll agree the results here aren’t likely to be pretty.

So product-oriented leaders everywhere…remember the tale of Gustavus Adolphus and the Vasa Royal Warship and mind the meddling with the engineers!

Transparency Rules

I think each and every one of our 13 core values at Return Path is important to our culture and to our success.  And I generally don’t rank them.  But if I did, People First is a leading contender to be at the top of the list. The other leading contender would be this last one in the series:

We believe in being transparent and direct

The big Inc. Magazine story about us last year talked a lot about our commitment to transparency and some of the challenges that come with being transparent and direct with people. I’d like to highlight here some of the benefits of being transparent, and the benefits of being direct (sometimes those two things are the same, sometimes they are different).

Transparency’s benefits are so numerous that it’s hard to pick just one or two themes to write about, but my favorite benefit is empowerment.  Especially in a world where information is increasingly available and free, hoarding it comes at a high cost.

• If everyone in the company knows that you’re short of plan and disappointed about that, the majority of people will exercise hawkish judgment about expenses.  The opposite is true as well.  If people know you’re running ahead of plan, they will be more willing to take risks and make investments. Without transparency of financials, people are just more in the dark and looking for all answers and judgment to come from above
• If everyone on your staff understands the process you went through to make a tough call about an element of your strategy, they are not only more likely to understand and support the decision, but they learn from you how to make decisions in the first place
• If your Board knows you’re having a tough quarter from the get go, they’re not surprised at the quarterly meeting and don’t force you to spend painful and precious minutes in the meeting On the firing line reporting on the details. Instead, they can spend time leading up to the meeting thinking about the details of the problems and how they can help or what insights they can bring to bear

Transparency does have some limits, even today.  There are three main limits we run into. One is compensation — still too touchy and wrapped up in people’s self esteem to post on the wall (though I have heard about a couple companies that do that, believe it or not). Another is terminations. Although you might want to tell the company that you fired Sally because she wasn’t carrying her weight, the long term value you derive from dignity and kindness trump any short term value you might derive from such a statement (plus, people know when Sally isn’t carrying her weight, anyway). The third limit to transparency is around half-baked ideas. Although you might sometimes want to try ideas on for size publicly, you have to be careful not to send people scurrying off in the wrong direction just because you blurted something out in a meeting.

The second half of this value statement is about being direct.  Being direct mostly has benefits in terms of efficiency. You can be direct and still be polite and kind.  But being direct means not beating around the bush, being political, or being conflict avoidant.  It means nipping problems in the bud and saving yourself time or money in the long run.

• If you are direct with an employee who is not performing well with data to back it up, the employee has a much better shot at improving than if you delegate the feedback to HR, wait for the next annual performance review, or go passive and skip the feedback entirely
• If you are direct with a boss who you think is treating you unfairly, your odds of fixing the situation go way up
• If there’s bad news to deliver, be direct about it — look the other person in the eye, deliver the news crisply and succinctly, and as quickly as you can after finding it out or deciding on it yourself

Avoid euphemisms at all cost. Telling someone you “might have to rethink things” is not the same as saying “I will have to fire you if xyz don’t happen in the next 30 days.” Saying “xyz would be good for you to do” is not the same as saying “the way for you to get promoted is to consistently do xyz.”

Being transparent and direct are increasingly table stakes for successful companies full of knowledge workers who want to be empowered and clear on where they stand.

I’ve really enjoyed writing all of these values out in living color. I will do a wrap up post shortly.

Why I Love My Board, Part III

My prophesy is starting to come true.  In Part I of this series four years ago, I asserted that

Fred may be the only one of my directors who has done something this dorky, this publicly, but quite frankly, I could see any of us in the same position.

Now, Brad Feld is no shrinking violet.  As far as I’m concerned, he made his film debut in the memorable “Munch on Your Bones” video (short, worth a watch if you’re a Feld groupie) something like 6 or 7 years ago for an all-hands meeting I ran.  But his newest short feature film, “I’m a VC,” made with his three partners, Jason, Ryan, and Seth, is a must-see for anyone in the entrepreneur-VC set and puts him up there with Fred in the pantheon of “this dorky, this publicly.”

Short of declaring failure and shutting down your company, laying off employees is the worst thing you may have to do as a startup CEO. I’ve had to lay people off on three separate occasions. It was difficult and emotional—those days were the worst of my career, and probably rank in the top 10 worst days of my life, period. This isn’t firing for cause—employees aren’t being asked to leave because of their own failings. They’re being asked to leave because the company can no longer afford to keep them. It’s not their fault.

It’s a truly awful process. Some CEOs will fall into the trap of thinking that because it’s invariably messy, it doesn’t matter how you do it. I couldn’t disagree more. Layoffs are bad, but how you handle them makes all the difference in the world. Here are a few best and worst practices for orchestrating layoffs.

Best Practices

1. Cut earlier and deeper than you have to. You really, really don’t want to go through this a second time. Assume you have less runway than you anticipate, and cut early. Cut more employees than you think you need to in order to reduce the risk of a second round of layoffs. Things are always worse than they look, even when the situation is bad enough to consider layoffs. Financing will take longer than expected to come through, receivables will dry up, and so on. 

2. Remove poor performers. You have no choice but to remove people if their positions are being cut altogether, regardless of performance. However, you can also take this as an opportunity for some major house cleaning. Just be sure to work with someone (a lawyer) who can help you navigate the legalities—particularly if you’re dealing with employees outside the US. 

3. Plan your talking points in advance of meetings. When I’m planning all-hands meetings, I tend to write bullet-point notes and talk freely instead of scripting my comments—but not for this. A round of layoffs is likely to be one of the most emotional moments of your career, and when you face your employees to deliver the news, you won’t be in your usual headspace. Don’t wing it. Plan everything you’re going to say—both to the individuals being let go and to your team as a whole—in advance. How you handle these meetings will depend on the size of your company and how many layoffs you’re doing. Regardless, you want to communicate respect for and appreciation of your employees throughout the process. 

4. Follow layoffs with an all-hands meeting. Layoffs are emotional for the entire team. Follow up with an all-hands meeting to explain what happened, why you made the choices you did—preferably with metrics to back up your decisions—what’s next for the company, and whether people who weren’t laid off are at risk in the future. (Be honest!) Ideally, the people you’re laying off should be included, too. You want to honor and thank them in as public a forum as possible. For those who remain, it’s important to cultivate security and trust. However you’re communicating with your employees, you’ll need to increase your efforts, and clarity is always better. Let them in on the state of the business, financials, and expectations. You don’t want to skip over the pain that comes with layoffs, but you do need to be prepared to move forward effectively. 

5. Treat employees who were laid off with dignity and honor the work they did. This will come into play when we talk about what not to do, but it’s important to remember that they’re being laid off for no fault of their own. One meaningful thing you can do is help people find their next step. Promoting the profiles of your former employees on job boards, portfolio lists, etc., offering your own connections if it’s relevant, or giving excellent referrals when you can are all great places to start. Severance is also key. Be sure to consult your board and follow your company policies, if you have them, then be as generous as you can afford to be. If you can offer a safety net or bridge, do so. 

These folks will still be alumni of your company, so the way you handle them personally will impact how they talk about the organization, rate you on Glassdoor, and refer to you as a leader. Every step of the process matters—whether it’s how you broke the news, how public things were, how helpful your team was, how much you paid—and will impact your company’s brand as an employer and your own reputation as a CEO. 

Worst Practices 

1. (Per above) Do not assume, because layoffs are awful and messy no matter what, that it doesn’t matter how you do it. It absolutely matters. 

2. Do not treat the people you fire like criminals. Don’t hire security guards or bring boxes into the office before breaking the news. Think very carefully about what systems you need to restrict access to, when, and whether there are any loopholes. Sure, you don’t want someone to be able to download a whole list of contacts from HubSpot. But do you really want them to be cut off from their email, calendar, and personal contacts? Shouldn’t you work with them to set up an autoresponder or figure out what happens to their email?

3. Do not promise this will never happen again. You can’t predict the future. You can say “we made the best decision possible, so that hopefully we won’t have to do this again.” Offer reassurance through facts and transparency rather than empty promises. 

4. Do not delegate the responsibility for deciding to lay off employees. As the CEO, this decision is yours to own. Also, do not blame someone else or the economy. Circumstances contribute, but at the end of the day, the buck stops with you, and again, you’re the one making the decision. 

5. Do not make mistakes about who is on which meeting invitation list or which employment list. Double check the list yourself, then have someone else check it. 

FAQs

I held a webinar recently with about 20 CEOs on this topic, and there were a number of questions that came up with interesting crowdsourced answers. Here are some snippets of some of them:

Q: How much severance is the right amount?

A: This is impossible to generalize—if you’re really out of cash, you may have your hands tied. If you can stick to your normal policies, you should. Companies represented on the call tended to give 1-2 weeks per year of service. Other thoughts that came up were: (a) offering a long post-termination exercise period for vested options, (b) accelerating some vesting, (c) creating a Salary Bridge program, which we did once at Return Path. The Salary Bridge program offered people an additional X weeks of continuing severance beyond the standard package if they still hadn’t found a job (but were trying and could show us they were trying) after their severance ran out. Very few people needed this, but the goodwill from offering it was huge.

Q: Have you ever considered salary cuts?

A: Yes. Usually a big layoff will come with some kind of salary cut for those who are staying, even if it’s just executives or just you as the CEO (which is more symbolic than anything else, but symbolism matters). Companies also had experience with doing salary cuts and reinstating the salaries as soon as the economic situation improved. One company talked about doing a 5% salary cut but then offering everyone a 10% bonus based on company financial milestones. In situations like this, it’s also a good idea to share metrics. How many jobs are you preserving by making cuts? 

Q: Do voluntary termination programs work? 

A: They might make you feel better, but be wary of doing them lest you lose key people you don’t want to lose!

Q: Can I expect additional employee attrition after a layoff?

A: Almost certainly. Any time you jolt the system, you’ll produce some unintended consequences. People will feel less stable in their role. Do your best to reassure key employees—even to the point of bringing a couple of them into the know immediately ahead of a layoff—so you don’t lose more people you don’t want to lose. Be wary of offering additional compensation or bonuses for them to stay, unless you are promoting them into expanded responsibilities (which can make sense if you’re consolidating things). Offering some people a raise “for no reason” while you’re letting other people go isn’t a great look.

Q: What about customer communications?

A: Our group was very mixed on whether or not you should do proactive external communications about a layoff. If you run a B2B organization, being a little more transparent with customers shows them you care about them—and gives you an opportunity to talk to them about any changes that might affect them, their service team, or their service levels. In a B2C organization, you’re likely either going to do something public like a short, empathetic blog post, or nothing at all. In all cases, please make sure you have a well developed internal FAQ and clear policies about who can and can’t talk externally as a company representative before doing a layoff so you’re not caught flat-footed.

Layoffs are messy and unfortunate, but you can still handle them artfully as a leader. How you handle layoffs will impact how your company recovers, it’ll impact your reputation as a CEO, and most importantly, it’ll impact the lives of the employees you laid off. I talk a lot about having a people first culture. One of the things I’ve learned about building companies with this in mind is that it’s got to be true all the way through. Even when you resort to layoffs, the people come first. 

(This post also appeared on the Bolster blog.)

As part of the new section on Exits in the Second Edition of the book (order here), there’s a specific chapter around handling the post-sale transition and integration process.  

No two transitions are exactly the same.  If the buyer is a financial sponsor, you may have the same job the day after the deal closes that you had the day before, just with a new owner and new rules for you.  Sometimes you’ll stay on with a strategic buyer as the head of a division, or the head of your product.  Sometimes you leave on Day 1.  Sometimes you leave later.  

But the most important thing you can do is remember that once the deal is over, it’s over.  That’s why an honest answer to the question, “Are you ready to let go?” that I posed in an early post is so important. You may or may not be the CEO, but now you definitely have a new boss, and in many cases, a boss for the first time in years. And you are no longer in charge.

“Even though the deal was called a merger,” I once heard Ted Leonsis tell the Moviefone founders a while after AOL acquired Moviefone, “please remember that you have been acquired.” Your job is to figure out how best to set your team and products up for success in the new environment, regardless of how long or short you plan to stay at the new company. 

We tried to focus our transition at Return Path to Validity in a few ways:

• For employees, we spent most of our energy and our capital setting things up in the deal documents before closing, recognizing we’d have no control of things after the deal was signed.  Things like how much severance people would get if they were let go, and for how long post-deal, how much their comp could change, whether they could be required to move – those are all things you can negotiate into a deal
• For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years.  Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO.  Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack.  This was a really important way we all got closure on this chapter in our lives
• For the new owners of the business, our objective was to be of service to them, knowing they’d want to run it differently.  So, for example, every time our new owners from Validity asked me a question (“Should we do X or Y,” or “Should we keep person A or person B?”), my answer was never simple. It was always, “What’s your strategy with regard to Z?” and then my advice could be in context, as opposed to thinking about what I would do in the prior context.

There are more details on this in the new section on exits in Startup CEO:  A Field Guide to Scaling Up Your Business.

One of the new sections in the Second Edition (order here) that I’m excited to share is a deep dive with several chapters on selling your company.  The next few blog posts will share some of my thinking on the subjects as they’re arranged into chapters in the book.  For many startup CEOs the culmination of their life’s work is an exit of some kind (other than being fired!). Personally, there were a range of emotions surging through me when we got to the point of a sale and while the financial reward can be enticing, there are a lot of things that you start to think about, like all the things you created, all the offsites with your team, the good and bad times and, especially, the deep relationships you’ve developed over the years.

If you’re a founder entrepreneur who has led your company for several years, the odds are you have a significant amount of emotional investment in your company, too.  For many entrepreneurs, the company is a deeply embedded part of their identities as a human – right or wrong, for better or for worse. 

I said in the First Edition that entrepreneurship is full of extreme highs and lows and the most difficult thing to accept is when they happen at the same time. Nothing describes the process of selling your company more accurately than that saying because you’re gaining some financial reward, but you’re losing your life’s work. You’re also creating some chaos and uncertainty for all your employees.

One of the most important questions you can ask yourself is, “Am I ready to let go?” For me I used a simple litmus test to help answer that question and I used the answers to these four questions to figure out the sell-don’t sell dilemma:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

You can turn these questions into a scale if you want to be more sophisticated but there are two important points: one, you have to do it and two, you have to look at all four questions as really just providing one piece of information. If I walked into an executive team meeting and said, “I’m not having fun at work,” my team would probably look at me and say (or think to themselves), “Hey, buddy, suck it up.” They’d be right, but if you have low scores on all four questions, that tells a different story. 

So how do you know when it’s time to sell? Usually there’s an inflection point of some kind–either positive or negative. On the positive side, you can receive an out-of-the-blue inbound offer, something you never expected and believe me, that will get the juices flowing! Or maybe when you look two years out you realize that your company is at its highwater mark in valuation, so it becomes a timing issue. Sometimes you can have a major internal problem related to the cap table–a founder with a lot of stock needs liquidity or you need to push this person out of the company. Institutional investors can require liquidity too, and while it’s possible to buy out shareholders or create a debt / equity financing, you might think about selling the company instead.

Other points on selling your company that I make in the Second Edition revolve around who you sell to (financial buyer, strategic buyer) and what the likely outcome of those types of sales are for you and your employees. You’ll need to brace yourself, your team, and your company, and your family for a major impact–the sales process is disruptive, non-linear, and intense and it’s not done until the final agreement is signed. 

Above all else, There is no right or wrong answer here about selling your company.  But there probably is a right or wrong answer for YOU.  That’s the most important thing to think through, deeply, at the early stages of working on selling your company.

Today marks Return Path’s 16^th anniversary.  I am incredibly proud of so many things we have accomplished here and am brimming with optimism about the road ahead. While we are still a bit of an awkward teenager as a company continuing to scale, 16 is much less of an awkward teen year than 13, both metaphorically and actually. Hey – we are going to head off for college in two short years!

In honor of 16 Candles, one of my favorite movies that came out when I was a teenager, I thought I’d mark this occasion by drawing the more obvious comparisons between us and some of the main characters from the movie.  My apologies to those who may have missed this movie along the way.

Why we are like Samantha (Molly Ringwald):  No, no one borrowed our underpants. But we can’t believe that people forgot our birthday either.

Why we are like Farmer Ted / The Geek (Anthony Michael Hall):  Meet my co-founder, George Bilbrey. I mean that with love.

Why we are like Jake (Michael Schoeffling):  Meet my other co-founder, Jack Sinclair. The shy, good looking one.

Why we are like Long Duk Dong (Gedde Watanabe):  We have only been in our newest business, Consumer Insight, for five minutes, but we already have a whole bunch of dates.

Why we are like Grandpa Fred (Max Showalter):  We’ve been around long enough to know the ways of the world, not to mention all the good wisecracks in the book.

There you have it. Year 17, here we come!