Category Archives: Startups

About finding your place

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.

My talk for TrueAccord’s 2018 Holiday party

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.

What happens after you’re hot

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.

Mercenaries

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.

Solving problems when growing is more complex. Here are some ideas.

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.

Staying on the rollercoaster gets easier over time

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.

Why I’m back to blogging

I haven’t blogged here for quite some time before July 2018. Running a company and having a young family preclude spending much time on anything but. However, as TrueAccord scales I find that writing makes more sense for a few reasons.

Writing helps me organize my thoughts. As I noted in the 50% rule I spend more time thinking about strategy, organizational design, and other topics outside of firefighting. Writing helps solidify my thinking and communicate it effectively.

Writing and podcasting are also better distributed than keeping my thoughts to myself or just sharing with my team. Better distribution of ideas increases the chances of finding like-minded people. If some of them choose to take part in TrueAccord’s journey, we all gain.

Finally, the supply of content for growth stage companies, which is the stage I’m currently interested in, is limited to VCs and semi-retired operators. I think we’re missing the perspective of people who are immersed in the day to day of it.

So, short blog posts written whenever I have time, discussing a top of mind topic, hopefully edited for brevity and clarity. Thanks for reading.

Subprime Blindness is holding back the next big break in fintech

In December 2017 Bloomberg posted this infuriating story about a man who was hounded by phantom debt, and how his crusade took down a Bad Guy (recently sentenced to almost 17 years in prison). It’s a captivating story with a happy ending, but one quote really caught my eye:

Therrien says he paid back the debt promptly. He was offended by the Lakefront woman’s suggestion that he was a deadbeat. “I’m a person who believes in personal friggin’ responsibility,” Therrien tells me. “I signed an agreement. And I fulfilled my obligation.”

This quote demonstrates one of several key misperceptions of consumers in debt. It’s something I like to call “subprime blindness”, a deep seated lack of understanding of and empathy for the consumer’s experience, motivations, and psyche, and it has wide ranging effects on our ability to start, fund, and scale solutions for the debilitating debt problem in developed markets.

Subprime blindness usually takes one of two forms: on one hand the condescending “it would never happen to me” approach, looking down on people in debt. This group thinks of debtors as morally inferior, deficient people choosing to remain in debt. The other is complete disregard of the reason most people are in debt, assuming everyone can afford to pay their debts if they were only afforded a convenient way to do so. Many investors I talk to have a story about debt, usually missed copay or some lingering internet subscription. To the well off it’s clear that they, and everyone they know, would pay if they just got a polite message.

Neither approach is correct. The majority of consumers end up in debt because they lost a job, had a medical emergency, or experienced another significant life event. These are not careless spenders or malicious consumers who couldn’t care less about their debt. They are often trapped and are doing the best they can given dire circumstances. Subprime blindness stigmatizes being in debt and hampers any ability to offer long term solutions that improve financial health and build equity.

This is what TrueAccord is solving. Radically changing debt collection is just step one. Our product relies on a radical—yet simple—alternative to Subprime Blindness: that consumers in debt are experiencing a temporary difficulty, and treating them like valuable customers will not only lead to better debt collection results, but will also help them build equity to eventually exit the cycle of debt.

Power doesn’t corrupt.

People say that power corrupts and I take issue with the simplification. “Power” (i.e. the ability to influence another’s life, in this instance) in itself doesn’t corrupt, but the realities that come with it sometimes do. Influence distances you from others (this is often worded as “it’s lonely at the top”), the distance creates alienation, and if you’re not careful, it erodes empathy. That’s the danger zone.

We’re sold on the role of the leader or power broker and how amazing it is to be in control. I love being CEO but there are elements of the job that are grating and problematic and must be managed. One of the most problematic elements is people management at scale. Early teams may be bound by personal relationships and a shared sense of mission but scaling cannot (and shouldn’t) create a homogenous team. By your 100th employee you have a decent chance of hiring someone who grows to dislike you, someone who’s a “coaster”, maybe a psychopath. You’ll hire a bunch of people who have different motivations, are in a different spot in their career, or are just different than you. You’ll need to fire people. You’ll face criticism that may feel deeply unfair. You’ll also hire amazing people that will do incredible things but for type-A people who become CEOs it’s the criticism that registers the most.

All in all pretty stressful if you can’t handle it.

Some try to deal by referring to their team as a “family”. That’s deeply wrong because the word “family” implies a level of commitment that doesn’t exist in companies. You don’t fire a family member and they don’t leave you. You don’t negotiate base pay with your uncle. Thinking of your team as a family creates unreasonable expectations that are bound to disappoint.

The more common way is to be jaded, feel betrayed, decide that employees “just don’t get it.” That’s the alienation that leads to eroded empathy. Thinking of people like chess pieces. It’s arguably a natural response based on research telling us that our frame of human reference can hardly encompass more than 50 people, but it’s also the wrong sentiment and must be resisted vigorously.

We have to hold on to empathy. You can partly manage this issue by thinking of your public self as a separate persona (I sometimes do) but at the end of the day you must accept that having influence over others opens you up to be influenced by them. It’s a two way street. My old martial arts Sensei used to say that people think of strength as not being dependent on anyone, but “We weaken ourselves by accepting our dependency on others and their dependency on us. That is true power.” I like this sentiment. Holding on to empathy is crucial. It’s also easier when you take care of yourself and have a support network that keeps you grounded.

The 50% rule

Talking to first time CEOs and executives in high growth companies, the thing that overwhelms them the most is the nagging feeling that they have to actively operate the business or everything falls apart. This often leads to exhaustion, mental first and then physical, which in turn hurts their ability to do their actual job.

Like most other things, I had to learn this the hard way and was forced to hire lieutenants during my first stint as a senior manager. Steve Jobs was once quoted that about 50% of his time is unstructured (can’t find the quote now). I think that’s roughly true. Spending time away from tactical responsibilities allows you to:

  1. Think strategically. One CEO told me how the first time he took a vacation after 4 years in the trenches led to deeper thinking and an acquisition by a public company. Worrying about tactical issues drains that capacity for strategic thought.
  2. Fix major issues. As a senior exec you’re going to get involved to steady the ship, right a wrong, save a major relationship. This is especially common in enterprise startups where you’re often fodder for the client’s senior execs to chew on to protect your team. This is both stressful and humbling and cannot be done if you’re exhausted.
  3. Convince. Once you reach a certain size it’s not about just fight or flight anymore. You have a large team of opinionated people and you need to inspire, convince, and direct them instead of practicing battlefield command and control.

The amount of time I spend thinking, talking, and writing about the business rather than creating anything will surprise anyone and stands in complete contrast to the “creator” myth that startupland loves so much. As a growth CEO it’s my job to become an ideas merchant, not a builder. Staying at the right level of abstraction and leaving a lot of unstructured time is critical.