Why do I do what I do? I could quote Ozymandias or the story about the Businessman and the Fisherman. Instead, here’s this tweet from Andrew Wilkinson.

What a stark difference from self indulgent “How to be Successful” twitter nonsense threads from SV luminaries yet, still, too prescriptive and infused with unacknowledged privilege. It’s not that he’s wrong; it’s the distinct “welcome to everyone else’s life” vibe, the discovery of the joy of fishing once you’ve built the business rather than just enjoying fishing in the first place, that I both strongly identify with and feel is, at the same time, incredibly ridiculous.

I don’t have any aspirations to tell others what to do. The past decade has been insanely good to me, through a combination of luck and hard work. Coming into this decade, and starting the fifth decade of my life, I’d like to remember that the Big Things we think matter, really don’t that much. That I matter a lot to a few people and I don’t matter all that much to most people, and that’s just how life is. That after satisfying my basic needs it’s more important to think whether I should do something rather than whether I can. I will continue making mistakes, but maybe less. I hope to enjoy the journey more. Most of all, I hope to not take myself too seriously.

A few years ago one of my HR people suggested that I start having small CEO dinners with teams as a way to get to know people, talk about the company, and create another forum to exchange ideas. I liked the idea immediately. Earlier this year I also ran across this story about Greg Popovich and how he uses dinners for team building. It all made sense: eating is a communal activity and connecting around a shared meal is human nature (though we go to a reasonably priced tapas place in SF, not a Michelin-starred restaurant).

Since I’m not much of a smalltalk aficionado I had to find a structure that worked for me, and I settled on personal histories. Each participant (these are usually very small events of up to 6 people including me) spends some time talking about their personal history, in as much detail as they would like, and answer questions from others if they’re open to them. I’ve listened to some incredible life stories and perspectives this way and even more than they helped my team connect with me, CEO dinners helped me connect with my team beyond the 150 person point, one that have I never crossed before as CEO.

I found that most people have a really hard time talking about themselves, even if they desperately want to share. I also found the people’s stories change as they attend more dinners, either because they highlight different aspects of who they are, or because they’re more comfortable sharing. I’ve had to learn to ask questions in a non-intrusive and empathetic, genuinely curious way, to get people to open up. It helps that I really like these people but it didn’t happen by itself. Naturally I also put my foot in my mouth several times with ill-timed questions. It’s a process.

Having small-forum CEO dinners that people choose to attend, and learning how to ask people questions became an important way for me to connect with my team, especially as it is growing. I recommend you try it. Just don’t take my usual table at [restaurant name redacted].

A few weeks ago I made a silly Twitter joke about starting a fund that invests $300 to make you a unicorn. 99.99% of the readers got it. A couple dozen people who showed up in my DMs and pitched me seriously did not. At some point I even asked what they’d do with $300 and one guy said “maybe buy a ticket to an investor meeting”.

This isn’t good. Not only because it reeks of desperation, but because it signifies a fundamental misunderstanding of venture capital funding and how to use it. I see two reasons for this misunderstanding: founders internalizing the constructed narrative around VC funding as the panacea for tech startups, and VC partners’ branding as enlightened king makers. Both are wrong.

Not enough people talk about VC funding being a tool in a tool box, and those who do often talk their niche position rather than make a general argument on how companies can grow. Companies flush with cash also tend to make a lot of noise (then mostly die with a whimper) on “tech blogs”, the startup world’s Instagram. In addition, many founders have been mostly in school, where you study in a constrained system and get graded by someone, so the North Star metric of funds raised seems appealing.

This is insane. It creates crazy situations. I don’t talk to many early stage founders and I’ve already come across people who are trying to raise millions to fund products that 1000 users could pay for. A two-digit team with only one developer and no one else even learning to code. A team of “business founders” unable to recruit a single developer, raising money to employ contractors. If this sounds like your company, stop raising right now. You’re already failing, and if by miracle you manage to raise funding you’ll just fail slower.

The other issue is the VC narrative. Most VC partners are smart and talented people who mean well and try to do right by everyone. They are also virtually indistinguishable; much like buyout firms correctly think every technology company tastes like chicken (Robert Smith WSJ story here), most VC funds are commoditized agents, pulling money from common resources and deploying it into an undifferentiated deal flow. As commoditized agents do, they invest a lot of time in branding, focusing on outsized successes (infrequent) and conveniently tucking away failures (the norm). Founders fall in that trap like many others do, and hope to be the next anointed genius, talking about “investors who can help us” with starry eyed devotion. It doesn’t last. VCs usually can’t really help you. It is not the VC’s fault and they’re not the bad people here. It’s just reality.

If you’re starting a company, especially if doing so for the first time, you owe it to yourself to understand all the tools available to you. You have to think clearly what success means, and plan accordingly. See yourself, investors, customers and other players for what they are – imperfect players playing a game. Don’t lose yourself in it.

I have a chief of staff at TrueAccord as of 2019 and I had one at Klarna. I see people hiring for chief of staff who don’t really have any staff, which is interesting. I think CoS became a fancy term for an executive/personal assistant or a stand in for ops manager, and that’s unfortunate especially for people who take this mislabeled role and then try to get hired as a CoS under someone who knows what to expect.

So by elimination, what a CoS is not: they are not in charge of the exec’s calendar, other than for meetings that really manage staff (e.g. staff weekly operating meeting, KPI dashboard, monthly and quarterly planning, etc.) They shouldn’t be doing your expenses or getting lunch when you’re in back to back meetings. There’s a place for an assistant but a CoS isn’t it. A CoS isn’t an operating executive either. You hire an executive to do a job you’re currently doing, only better than you. They are often a subject matter expert (even if that expertise is people or general management) and they take on operational responsibilities and manage to goals through others. While in a big enough company the CoS may manage the office of the executive (including the assistant, for example), they are not operating independently of the executive.

A chief of staff is an extension of the executive. They often have some overlap in interest, capabilities, and responsibility areas with them. Other than operating cadence for the exec’s staff, they mostly work on ephemeral projects aimed at progressing the exec’s tactical interests: solve a tactical issue, pressure the organization to progress on a specific task, and so on. While they represent the exec they are not them, so they can act with similar authority but not be as intimidating which is helpful when putting the pressure on lower levels of the organization. At TrueAccord, my CoS facilitates weekly leadership meetings, supports budgeting and board meeting prep, and then works on a variety of tactical projects, spending time with analytics, client success, accounting, or sales as needed. There is a lot to be gained from hiring the right person to be your CoS to do the right type of work. It’s a waste to do so to make yourself feel important.

It happens that a man is born into a foreign land.

It happens that although he has a father and a mother, brothers and sisters, a language and culture – he is actually from someplace else, and he doesn’t know that he is. He agonizes his whole life, until he realizes it, and starts his journey back to his homeland, one he never visited and no one can guarantee even exists.

This man is born into hell, and initially he doesn’t know that it is hell that he was born into.

He goes on to live his life, stumbling over and over, and only after a long while something happens: a moment of grace, when he gets to see – if only for a fleeting moment – his own place in the world. A torn postcard from his place, let’s say. Or someone who’s from there that passes by and smiles – a moment that changes his life, because he suddenly realizes that that place exists. That he isn’t dreaming. That there is a better life than the one he’s living now. And, of course, at the same moment he realizes that he’s living in hell.

(Uzi Weil, originally in Hebrew. The bad translation is mine.)

***

I was standing in the middle of the dance floor, suited up. The speakers were blaring pop music from the stage above the DJ, where one of the country’s most popular singers gave a full performance. I was surrounded by tall, beautiful, extremely trendy people drinking cocktails and yelling over the music, or taking a photo of the singer on their phones.

This launch of a new European investment fund was wrong on so many levels.

***

I fell in love with Silicon Valley on my first visit. It wasn’t nature or the weather. It was the people. So charmingly approachable, and enthusiastic, and authentically interested in technology. So awkward and obviously using well rehearsed communication protocols that they reverse engineered. It was geekdom. I was hooked.

It took me two and a half years to get my Green Card. When it was time to prove my vaccination history for the application process I just re-took all of them, because it was much shorter. My corporate-appointed immigration lawyer asked me to stop pushing her to handle the process faster. I was obsessed. I was going to be a part of the action. Silicon Valley was my place.  

***

Every attempt I’ve seen to replicate the Valley misses by a long shot. It happens when you focus on appearance instead of essence, and forget history. It’s easy to focus on Elon Musk, the guy with the perfect hair who was dating that actress or singer. Who cares. Elon Musk who started PayPal was a geeky, balding guy who teamed up with a crazy hedge fund manager who wanted to overthrow the government with a new currency, and fought him tooth and nail until they both became rich. Microsoft is this software behemoth and Bill Gates is a billionaire but he’s also the world’s worst dad dancer who forgot to eat if he got into an argument, and destroyed his opponents without making eye contact.

Try to observe what makes this place tick. Listen. Don’t fixate on the end condition. Don’t fixate on the glamour and survivorship bias. Silicon Valley is what it is because geeks built it and geeks maintain it. That’s the one thing those other ecosystems get wrong. They have lunch meetings and take five-week vacations. They won’t help unless you give them equity. They promote within their well-defined cliques. They try to get a project funded with a part time CEO and a 20% “chairman of the board”. They invite models and pop stars to launch parties and think the deal flow will just reveal itself. That’s missing the point.

***

Popular culture looks at the Valley’s successes and misgivings and weaves a narrative. Sure, it’s over funded, and over hyped, and over the top in many ways. It has a ton of problems. It’s starting to crack under the hype and abusive behavior by people who don’t get it. Silicon Valley is counter culture, even if what it counters varies and changes. It always tries to oppose, and sometimes forgets to lead. It is also a source of aspiration and inspiration to everyone in tech. It sets a tone.

Welcome, everyone, to our annual Holiday party. I’m so happy to see so many faces, people who’ve joined us this last year and people who’ve been part of the team for a few years now.

We’ve grown in so many ways as a company, and I want to take this time to thank all of you for your hard work.

I also want to tell you a story.

Lately I’ve been binge watching Chef’s Table on Netflix. I get inspired by people talking about their passion, so even though I’m not much of a cook, I love hearing others talk about cooking.

I watched it for a while and started noticing that there were episodes that left me inspired and ones that didn’t. And after some reflection, I realized the ones that didn’t inspire me were the ones with a glitzy success story focused on one lone genius figuring it all out on his own.

The chefs that inspired me were the ones who faced adversity. They experienced grief. They took time to figure things out. Their episodes showed their family, and friends, and coworkers —of people spending time, together.

Because it does take a village to build something great—a great restaurant, a great company. It takes a community. And the stories we tell about how we got here and what’s coming next matter. A lot.

When we started this journey five years ago, we had a simple story. We wanted to use technology to change debt collection.

Over the years, we grew. We added more people. We added more voices. Our story changed with the people who joined, because each person has added his or her own perspective.

With time, we realized that we have a bigger role to play than we first thought. We are not just about a great customer experience. We do much more than that.

We meet people at some of the worst times of their lives and we offer them a different story about debt, one that doesn’t rely on shame and guilt to collect.

We lead with empathy. We listen. We respect who they are, and where they come from. This is as important, if not more, as giving them the payment plan they were looking for.

What you do here, at our company, makes a difference to those people. We are entering 2019 with almost [redacted] consumers in our system. We [redacted] in a single year.

Everyone’s noticing. We even inspire traditional collectors to do things differently, from using our language to using new technologies.

Most of all, our customers are noticing—like [redacted], who wrote to us, saying “Your emails and messages were kind, understanding and indicative of the truth—which is that I’m a good person who fell on hard times, and was too scared, afraid and stuck to know what to do… You never gave up on me, and so when I could, I did everything I could to create a way to work with you to pay back my debt.”

We are writing this story together as we go, rewriting pain into hope and despair into inspiration.

Which leads me to you. To all of us.

I started having dinners this year because I was trying to figure out what makes a company great to work at after the first hundred people have joined—what attracts the type of people that makes work enjoyable.

This question led me back to empathy and our ability to listen to one another. To weave our stories together as we build something great.

All of us: those who had to grow up fast and those who took time to figure things out. Those who had sheltered lives and those who had to literally fight for their lives.

Those that faced rejection. Those that struggled to be accepted. Those who overcame adversity. Those who have failed, and yet still get up. And those who won. All of us.

Look around you. This is your team. This is your company. This is your story. What you choose to add to it may forever alter its nature.

The recent graduates thinking about their career paths. The seasoned veterans who joined to make us even greater. Everyone in between. It does take a village to build what we’ve built.

Now, I don’t know what the future holds. I think 2019 is going to be a great year. I think we’re going to continue to face adversity and win, again. I think we are going to expand our reach like never before.

No matter what we do, it’s going to be a great story. I can’t wait to hear your part of it as the year unfolds.

To where we’ve been, and where we’re going—together! Cheers to 2019.

I love learning from other CEOs, but it’s difficult. Most conversations with CEOs are disingenuous because they are always posturing, and contrary to what I used to think, honesty doesn’t always help them open up. Especially not in the distributed corporate that is Silicon Valley. Whenever I do get some authentic interactions, my favourite type of CEOs are those who founded and run companies that used to be hot, but aren’t anymore.

Note, not failed companies. Most of them run companies that are bigger and/or have higher top line than TrueAccord or ones that were acquired. They used to be hot because they operated in a hot segment and VCs were throwing money at them and their competitors. They raised a bunch because you eat when you’re fed. Some of them are running 300-500 person organizations with deputies with incredible pedigrees and well oiled sales machines. By all accounts they should be on the top of the world.

Like everything else, though, it’s not always the case. Interests aren’t as aligned once you’re not hot. Reasonable acquisitions are rejected, sometimes undermined, because investors think they can get a bigger number to put on Twitter. Founder comp doesn’t get updated as fast as their needs. The push for growth creates unprofitable behemoths that have to continue to raise from an ever shrinking pool of organizations (each managing more money than ever, for sure) and getting profitable seems like an ever elusive dream. Struggles for control are common and if founders are not, say, geographically removed or otherwise protected they face imminent risks to their role. Most of all, they are tired. The 5 year mark is a real thing, and yet these founders don’t feel like they can rest; sometimes they don’t even feel like they can hire a second in command because they fear a VC implant that will undermine them.

I learn a lot from these founders because they are grizzled veterans by now. They’ve seen a lot. Most of them will continue to succeed and the majority of their days and weeks are on a high note. It just serves as a constant reminder for me that there is life after being hot and the strings you agreed to when you thought this wave will never break create a pretty mean entanglement. It’s one of the most crucial issues we don’t spend time thinking about early on that comes back to haunt us later.

The rise of Silicon Valley and its financial success also initiated the rise of its mercenary class. These are smart, capable, well spoken people who spend more time building their career trajectory than making the teams they are a part of succeed. They have social media presence and impeccable resumes (of course). They expect people to talk a certain way, behave a certain way, care about a certain type of visibility.

Mercenaries want to work with me. Not all of them and not all the time but I do check the boxes for mercenaries. Exits, expertise, “serial entrepreneur” (please). I talk in that fast, cutting style and use SV vernacular because I’ve done most of my professional speaking in SV. In their limited pattern recognition I’m a strong positive.

Only I’m a false positive, because I won’t work with mercenaries. I curated TrueAccord’s culture to resist and repel mercenaries. The company is driven by a literally disruptive mission. Investors are curated because they have to believe in our long term plan. Employees are curated because I’m experienced enough to hire for talent and not for pedigree. There’s no elbow rubbing in the biggest DreamForce reception or getting on TechCrunch or writing up you “Three Tips To Giving Feedback” on First Review. These are distractions and the people who don’t get that need not apply.

As organizations grow they start to trade agility for scale and repeatable process. It’s mostly a healthy trade off but there are many instances in the early hyper-growth stage where the standard operating procedures they teach you in B School fail miserably. Executives can reverse the trend but they have to be both attuned to those failures as they happen and willing to make fast and tough decisions. Both of these behaviors can be perceived as impatience and not letting things “play out”. I’ve yet to see a bad situation solved with just patience, though. The ability to make tough decisions and cut through red tape is what separates greats executives from good ones.

There are three tools I’ve seen work, from the mildest to most extreme.

Resetting KPIs helps since what gets measured gets improved. Many times merely asking for a number (e.g. SLA) to be presented transparently will drive some change. Then, you have to reset priorities (can’t do everything at the same time) and get a time commitment to hit a goal (i.e. I will reach 90% SLA within two weeks). Change will still take some time because large teams work on building momentum, so this isn’t a good tool for a new type of problem, a systematic problem, or one that needs immediate change (not all problems do).

Hiring and reorganizing is more extreme but should be used more often in mid stage organizations. When transitioning from early to growth stage it’s often easy to forget that you have more managers, a better organizational backbone, and the budget to solve some problems with hiring. So instead of doing the above, executives add more responsibilities to an existing team. It used to work early on but when growing fast it’s hard to even maintain your current responsibility and the existing team will likely not give this new area enough attention. Identifying a problem then hiring someone (often more than one) to manage it is often the right solution.

Doing it on your own. As a founder CEO I love getting my hands dirty and it’s often not the right decision. However, as organizations grow they rely more on momentum and complex processes than thinking from first principles. Two years into TrueAccord I once asked the staff why we gave team updates in the order that we did. Not many remembered it was the result of me randomly ordering Trello boards when we started. Random decisions become gospel due to momentum and it’s often up to the executives to tackle a hairy problem, make it their top priority for a short while, create the way to handle it and then hand it off. This way you’re not only solving some of the problem, you’re also setting your team up for success and are more likely to hire an expert to build on your early iteration (while constantly criticizing it. Try to not take it personally).

These tools are effective and mishandling pressing issues can kill your business just as it hits scale. Don’t fret too much about people complaining about misalignment and the definition of success changing. As Tuckman’s model for team dynamic shows us, it takes time for teams to realign around a change in prioritize or structure even in the best of situations. As long as you don’t do it too often the teams will figure out a way to work. Having a problem and not measuring it or setting a goal to solve it is worse. Cut through the noise when you have to.

I was talking to an early stage CEO on the cusp of a pivot and last minute round extension, dovetailing on losing a co-founder. On one hand sounds pretty bad, on the other – it’s a day in the office for most early stage CEOs. By the end of the call he asked me if it gets easier over time. I always lose sleep in the first phase of a new role or company, no matter how experienced I am, but I do think it does get easier, in several ways.

Pre product market fit, every threat could kill your company. It’s absolutely possible your whole idea is worth nothing, that your entry point is invalid, that you spent too much. Post PMF and at scale, while the stakes feel higher, you’re not likely to lose the company (someone told me the other day “>$10m ARR companies don’t die” which rings true). Post growth the only thing to compare to is your day dreams and whatever photoshopped merchandise they’re selling on TechCrunch, where everyone is up and to the right and the sun is always shining. It stops being a material risk and starts being about your own psychology.

Once you reach a certain size, you’re also a bit more isolated from day to day swings. It may feel frustrating for founders who’re used to hands on work but it’s mostly good when someone else, often more qualified than you for a specific job, can handle fires. As you grow you have more, not less, issues to deal with and hiring and scaling well helps deal with them without handling too much of the emotional strain. Last month we had some fire at TrueAccord that was extinguished by a team of people, without my involvement, in just a few days. Three years ago the same issue went undetected for a month then took the whole team at least three non stop weeks to fix. I’d call that progress.

The last and probably most important thing is emotional maturity. With time you become more resilient – because you’re literally maturing with the company, because of additional experience, and because you’re starting to realize fires always happen and they must be taken in context and proportion. Mastery of oneself is important and if you reach said mastery, tell me how. I’m still working on this one.