Justin Samuel of EarlyDog: Five Things You Need To Create A Highly Successful Startup

An Interview With Paul Moss

…Purpose. This isn’t the same as perspective. Perspective is having the ability to wake up. Purpose is who you are when you wake up. You need to deeply know why you’re doing a startup. Most of us aren’t trying to get humanity to Mars. We’re just trying to improve the lives of people we love, make good use of the opportunities we have, live by our values, be happy, and generally be the best person we can be. Your company is going to be a major sacrifice for the next ten years of your life. If running your business doesn’t give you purpose or isn’t helping you figure out what gives you purpose, then you’ll run out of steam which in turn means your company will run out of steam.

Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup. I had the pleasure of interviewing Justin Samuel.

Justin Samuel is CTO of EarlyDog, a highly personalized managed hosting service setting the new standard for enterprise customer experience in managed AWS and Google Cloud. Together with co-founder and CEO Allison Samuel, they’re building an organization with a culture based on trust, learning, and growth. Before founding their company in 2012, Justin’s work as a security researcher included identifying major vulnerabilities in Linux package managers and designing secure software update systems. Justin earned a B.S. in Computer Science from the University of Arizona and an M.S. in Computer Science from UC Berkeley. Before EarlyDog, Allison ran a medical case management company specializing in complicated work injuries and, for over a decade prior to that, taught high school AP Chemistry while advancing science education reform. In addition to being a registered nurse, Allison earned a B.S. in Biochemistry and a B.A. in Philosophy from the University of Washington and a Master’s in Education from Antioch University.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

For many years, Allison and I wanted to run a business together. Since we met at the University of Washington in 1997, we’ve known great things can happen when we combine our skills. Not only are we massively impactful as a team, but we also love working together. I’m a specialist. Allison’s a generalist. I understand how to apply technology to solve problems. Allison understands how to organize people to solve problems.

After grad school, I launched ServerPilot, the first SaaS hosting control panel. ServerPilot was the right solution at the right time. I got serious about creating a new generation of automation tools for the hosting industry in 2011. For ten years before that, I’d been doing server administration and security management for hosting companies and digital agencies. At the time, cloud server adoption had only recently started to take off. People were still trying to use the old software from the shared hosting industry to manage cloud servers. I took a fresh look at the problem, not just what people expected at the time, and made ServerPilot. The timing was perfect as DigitalOcean launched around the same time, opening the floodgates of developers self-hosting on unmanaged cloud servers. The problems those developers face are exactly what ServerPilot solves. ServerPilot’s success allowed us to build an amazing team and think bigger.

I’d been dreaming of solving more fundamental problems in managed hosting well before ServerPilot. However, I didn’t have a vision for how to do the customer experience or company culture side of a service-based business 10x better than what currently existed. Technology innovation is in my wheelhouse, but the best managed service providers aren’t differentiated by technology. Even when I was working on the MVP for ServerPilot while in AngelPad, the startup accelerator, Thomas Korte pressed me on why I wasn’t creating a new type of hosting company as I knew it was a huge market in desperate need of innovation. At the time, I only wanted to focus on smaller problems where I had a clear vision. Years later, when Allison and I not only had the bigger vision but also a great team and revenue from our software products, it was a memorable life experience to be telling Thomas we were finally ready to change the managed hosting industry.

What allowed us to develop a vision for a 10x better managed hosting experience was Allison taking the driver’s seat. I started out as CEO and kept the focus on what I understood best, which was software. Allison had a nurse case management business at the time I started working on ServerPilot. Her business funded ServerPilot in the early days and she helped me navigate running the software company, but she didn’t have time to be fully involved. So, even though we dreamed of building a great company together, we waited until the software business was far enough along. In the meantime, we evolved our thinking as the industry changed. When we launched ServerPilot in 2013, Rackspace still dominated managed services but was almost a decade into their losing battle with AWS over cloud infrastructure. That created a growing innovation gap between what the major player in managed services was doing and everything that was becoming possible.

When Allison took over as CEO, her vision for tailoring the managed cloud experience to each business combined with her ability to create an organization where people who want to grow could thrive transformed our company from good to great. My dad’s known Allison since we were college students. When I told my dad that Allison was taking over as CEO, he told me it was the best business decision I ever made. In his career, he’d been an engineer, managed engineering and product teams, and was an executive in technology companies. He’s worked with great CEOs and he’s worked with CEOs that weren’t. He understands the huge opportunity we have is only possible with the right leadership.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

We did a thought experiment: “If we outsourced cloud operations for ServerPilot and our other SaaS applications, what would we want as the customer?” That put us on the right track.

If we outsourced our own cloud operations, we’d still want to feel like we were communicating with our own team who deeply understood us, our business, our goals, and our concerns. We’d want to interact with the same people regularly and develop meaningful, professional relationships with the individuals we worked with so we could have truly great and efficient communication. Any interaction where we were just another customer would mean we’d lost something important by not running operations in-house.

The clarity about wanting to feel like we were interacting with our own team helped us take new approaches when creating all parts of our UX, from how our customers and their developers communicate with us to rethinking the primary purpose of our user interface. We’d still want to communicate with our operations team by Slack, Zoom, and Google Groups, not through clunky support ticket systems and annoying chat boxes. We approached our user interface from a similar perspective by asking ourselves, “What information would give us confidence, save us time, make clear if there’d been communication failures on either our side or theirs, and make it easy for our developers to be highly productive?”

Allison’s always loved and admired great product experiences. A long time ago, I was focussed on using Linux on the desktop. Allison, on the other hand, started using an iMac back in the 90s. When Allison took over as CEO, she immediately turned her focus to bringing unexpectedly great experiences to managed services. From there, the biggest challenge was finding new ways to think about the problems we’re solving for our customers so we could root out hidden assumptions tied to traditional approaches.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Dallas Kashuba, cofounder of DreamHost, was one of those important people early in our journey. While in AngelPad working on ServerPilot, I cold emailed Dallas as a potential advisor and investor.

I’d known about DreamHost for years. Essentially from the beginning of shared hosting, they’d had the strongest reputation in the industry as a good business run by good people. Well before investing in us, Dallas was generous and helpful. He let us have free office space, made introductions, gave me insights into the industry you’d only be able to get from his unique perspective, and asked hard questions.

Certainly, Dallas was helpful as an investor and advisor. But Dallas also had an impact on me personally. Like me, Dallas came from a technical background, not a business background. There I was, in my 30s, lacking sleep, just left the PhD program to do a startup, no business experience, dreaming of the financial freedom that would allow Allison and I to solve bigger problems together. There he was, 15 years into his company with the financial freedom to do otherwise but still enjoying being involved on a daily basis.

Until around that point in life, Allison and I hadn’t prioritized financial freedom through making money but instead through living simply. Around the same time for each of us, some switches flipped in our heads. For me it happened while in grad school and thinking about what I’d do next. I realized how privileged I was with my technical capabilities and that few people were in a situation like mine where they could create wealth with software. I wanted to make use of that privilege to create the life for us I dreamed of, so I began an exciting but extremely stressful startup adventure where I immersed myself in entrepreneurial life which isn’t always conducive to happiness. Dallas was a great counterbalance to the startup world and a bit like a light at the end of the tunnel. I laughed about it then and still do now, but even though we’re about the same age and just took different paths in life, Dallas felt like a summer camp big brother to me.

What do you think makes your company stand out? Can you share a story?

We like to interact with and work with real people. That also influences who wants to work with us. It causes us to take the long view on relationships. When we come across great people or companies, we don’t take it for granted. We keep them in mind and look for the right opportunities to work together. And we know they’re doing the same with us.

Strengthening these long-term customer relationships over years through our software products made launching EarlyDog not just easier but vastly more successful and meaningful. Your first customer with any service has a huge impact on your team and your business priorities. The deeper that customer relationship, the better the mutual understanding and communication. That means more learning and more certainty you’re putting energy in the right things.

We had the privilege of EarlyDog’s first customer being an appointment scheduling app, Resurva, that had relied on our software products for almost ten years. Resurva told us long ago they’d switch to us for managed services if they could. There’s no other first customer that could have been more meaningful to us. Or more sobering. We knew them well and cared about their business. We’d seen how much they’d sacrificed to make it successful. We understood the impact of our service on their lives and families. Having real insight into the individuals putting their trust in us was exactly what we needed to set the right priorities while developing our service.

Being focused on creating a company culture where we each get personal value from working with one another has also helped us attract amazing people. Building a truly great organization requires convincing truly great people to join you. Just like you, they only get one shot at the next years of their life. Why should they spend a good chunk of their very finite life working with you? Our sincere focus on meaningful work, learning, and honesty comes through to people we’re recruiting to join our team.

How have you used your success to bring goodness to the world?

So much of the experience of being on the internet nowadays is not positive. But we at least have control over the content we create. We’ve come up with the following question to ask when creating content: would I want my family and friends to spend their time looking at this?

We want to have a positive impact on anyone who interacts with our site, with our writing, with the videos we create, with the interviews we do, with everything we add to the internet. That’s what caused us to engage a design agency like Fell Swoop to help us create the EarlyDog site. Even if we only impact a tiny part of someone’s day when they come to our site, we want that impact to be positive. Those little experiences throughout a day have a huge cumulative effect.

We carry that same focus on creating positive experiences to our Zoom calls. In the age of working from home, team meetings and sales calls are opportunities to make the mundane aspects of a work call interesting for the people involved. Why not pay attention to lighting, image quality, and what’s in the camera frame? By embracing the fact that we’re individuals working from home even though we’re representing our company, we also build trust and relationships faster which leads to better communication.

We also think creating a very personalized service in the way we’ve done it brings its own goodness to the world. The operative words there are “in the way we’ve done it.” Personalization has been abused in marketing, but I’m not talking about personalized marketing. The personalization we’re focused on is in how our customers interact with us and how our service feels to them. Internally, one of our guiding principles is, “How will we make each EarlyDog customer feel like they are the one and only?” Anything that exists in our customers’ dashboard or in the ways they communicate with us that feels impersonal, that makes them feel like just another nameless customer, that makes them feel like we didn’t build the service just for them, we work hard to identify and fix. Whether it’s a button in our dashboard that’s irrelevant to their use case or how we name their Slack channels, every way we can instill confidence and prevent uncertainty saves them time and energy. That saved energy allows them to be more effective, relaxed, and confident in their work lives as well as their personal lives.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The first was determination rooted in confidence in myself to persevere. I knew I was fully capable of being successful but that I had a lot to learn and learning those things was likely going to be more painful at times than I could imagine. Privileged as I am in many ways, I’m not a stranger to pain. I deeply believe if a young person never has to struggle their own way through hardship, they’re unlikely to end up being a healthy and strong individual, friend, family member, and member of society.

Hand-in-hand with determination was self-awareness. I’ve experienced being determined for the wrong thing before. We all have, that’s part of life. I’d gotten to a place in life where I knew myself pretty well. Or, at least, I’m appropriately self-critical. What that leads to is honesty with yourself. Honesty about your capabilities, your limits, your weaknesses, what you’re good at, what you need to learn, and where you find meaning in life. Knowing which situations set you up for happiness and success and which situations set you up for frustration and failure. When I make plans, I consider the situations I’ll be putting myself in and the varying levels and types of stresses I’ll face. I know many areas where I need to grow as a person, but I also know I’m not a superhero. For example, I try not to put myself in situations where success hinges on quickly overcoming character flaws, ego problems, or communication difficulties I haven’t sorted out in life yet. I love sorting out my issues, but putting yourself in situations where success hinges on suddenly fixing things you’ve been working on for years is not setting yourself up for success.

A third character trait I think was instrumental in my success was being a nuanced thinker. As a first-time CEO, there was so much I didn’t know but I constantly had to commit to decisions where there was uncertainty. In those situations, it’s tempting to delude yourself about your own level of certainty. Having thankfully gotten to a point in life where I don’t see things in black and white anymore, where I know there are many reasonable interpretations of any situation, made it hard to fall into traps of simplistic, narrow, blindered thinking even when mentally worn out. There’s a Richard Feynman quote I like about the difference between prejudice and bias. “As long as you are only biased it does not make any difference, because if your bias is wrong a perpetual accumulation of experiments will perpetually annoy you until they cannot be disregarded any longer. They can only be disregarded if you are absolutely sure ahead of time of some precondition.”

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I was never in a situation where advice I received was of higher weight than what my gut ultimately told me. It wouldn’t necessarily have been wrong had that been the case, but I can’t remember that happening. I certainly took advice into account and, depending on who was giving me the advice, how much they knew of my situation and the particular advice they were giving, what I knew about their view of the world and their priorities, how nuanced of a thinker they were, how much I felt I understood my own situation, and what other concerns and motivations I had that they weren’t aware of, I’d give their advice more or less weight.

That said, there is some generic advice — not specific advice from one individual to another — that’s bandied about in the startup community in ways that are harmful to many founders. To me, the most notable piece of oversimplified, overapplied, misunderstood, misrepresented, and harmfully hyped advice is that startups should be making data-driven decisions.

There are a lot of problems with the blanket idea that startups should be making data-driven decisions. Those problems include the fact that there are wildly different stages of startups, vastly different types of startups, hugely varied levels of statistics comprehension among founders, and painfully varied levels of statistics comprehension among the people giving advice in the startup community. When you combine those problems and many others with understandably uncertain first-time founders who don’t know what they don’t know, the result is often more than wasted time, energy, and money. Improperly making decisions based on data is a recipe for founders going in wrong directions at very early stages where they end up building a faster horse, at best.

Maybe you should be looking at data from day one, or maybe you shouldn’t for all of year one and year two. Maybe someone else running your business would benefit from looking at data but it would distract or derail you to look at the same data. No matter how or when data analysis will be valuable to your company, if you’re being influenced by small, biased data sets, you’re doing something wrong.

Can you tell us a story about the hard times that you faced when you first started your journey?

I deal with depression as a recurring part of my life. I’ve come a long way in understanding my brain better, but — to paraphrase Emo Philips — look who’s telling me this.

Winters are hard for me. When the sun goes away, so do the happy chemicals. And calling them the happy chemicals is an oversimplification, of course. And so is calling it depression. It’s ultimately mental health issues, with some physiological components and some psychological components. When you combine gray skies and short days with winter sunlight’s shallow angle of incidence, the winter is rough if your wiring is dependent on a lot of light.

During the times where you’re starting off in a difficult mental state, communication gets harder in ways you can never completely anticipate. There’s never ideal communication in startups in the first place as there isn’t enough time. That constant busyness makes it hard to notice when communication is getting worse, not just temporarily decreased. And the isolation that comes from failing communication can easily create a downward spiral.

Thankfully, I’ve always come out the other side of depression a stronger person. One thing I have on my side is that winter doesn’t last forever. Some people aren’t as lucky as me, their battles with depression aren’t seasonal.

Talking about this publicly is a major step for me. But it’s also a privileged one. When I first started this journey ten years ago, didn’t have employees, didn’t have a product, didn’t have revenue, didn’t have customers, didn’t have investors, didn’t have business experience, talking about mental health issues wasn’t exactly a way to instill confidence in the many people who needed to know I could handle what was ahead of me. And I don’t think that’s fundamentally wrong. Starting a company isn’t a game. People are trusting you with their livelihoods, their businesses, their money, their careers, their family’s security. It’s completely rational and healthy for people to look for signs of weakness in others they rely on. I’m just glad I get to pay it forward by talking about this now as I’ve had the benefit of years of reading about other founders’ experiences with depression.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

The main thing that allowed me to continue despite hard times was having a relationship that gave me so much purpose. I want to have meaningful experiences with Allison in this short time we get to be alive. Building this company together is one of those immensely meaningful experiences we want in life, and that includes the difficult parts as adversity is so much of what makes life rich. So, I have a perspective that doesn’t make me want to avoid the hard times altogether.

We aren’t people who would enjoy spending the rest of our lives on a beach. We want to overcome challenges together. We want to grow together. We want to have adventures together. We want to build things together.

The deep understanding that we want challenges in our lives gives us a lot of perspective on how to think about this company. Of course, you never know how you might change, but based on what we’ve known about ourselves for a long time, our ideal outcome has always been to create a company we both want to stay involved in for a long, long time. For that to happen, our work has to continually help us grow as people. What’s amazing right now is we not only get to create the company culture we want to stay involved in, we also get to experience the challenges of creating it together.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

For me, the most important part of navigating the emotional highs and lows — and when I say that I mostly mean the lows — of being a founder is having a deeper perspective of life and why you’re doing the things you’re doing. You can’t keep that in your mind every second, but hopefully every day you have some chance to see life as bigger than the mountain you’re currently climbing. A moment of perspective won’t suddenly fix your low feeling, but it can allow negative experiences to be more manageable and sometimes even valuable.

There are also risks from the emotional highs, even though it might sound funny and the highs are a blast. First, you can be pulled down a specific life path because of the highs and you might end up somewhere that doesn’t make you happy. Second, you can be set up for lower lows when the source of the highs comes crashing down. The preventative medicine is having something that grounds you, something that reminds you your business ambitions are shallow relative to what’s really important in your life.

Let’s imagine that a young founder comes to you and asks your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

The first question I’d ask is: what do you absolutely need to come out of the next few years of your life? What’s non-negotiable five years from now? If what you absolutely need is a functioning company that pays its own bills even if that company is just one person, then bootstrapping is the right choice. It doesn’t mean you can’t choose to take money later when the company is self-sustaining and you’re not feeling desperate.

If you want control over your life and it’s not an option for you to start over or work for someone else down the road, you have to maintain full control over your company. Take angel money if you need. Take friends and family money if they’d be fine losing it and they acknowledge that’s likely. But understand each investor’s rights and make sure the company’s direction can still revolve around your life until it no longer needs you and you no longer need it.

Venture capital should be thought of as rocket fuel. Think really hard before you put rocket fuel in the tank. You don’t want to get back on the road and realize you’ve put rocket fuel in your Subaru. The money will spend itself. You probably won’t like where you end up.

So, if the young founder believes a) they’re looking at a prototype rocket not a Subaru Outback, b) they’re ok with what life looks like if the company fails in a few years, and c) they’re able to convince reputable VCs to invest in them, then the founder should consider involving VCs in their company.

Ok super. Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.

The first thing most people need to create a successful startup is the ability to push themselves to think bigger and do bigger. In some cases, that means bigger than you’re comfortable with, bigger than what seems sane. In other cases, it means bigger than you’ve been doing in the practical period leading up to launch. It really is true that the amount of time and energy and pain required is approximately the same to create any size of successful startup. If you focus on something small, what you’re going to learn is small and what you’re going to create is small. Successfully executing a small idea will hurt just the same as if you were learning something big and creating something big.

The second thing you need is honesty with yourself. You of course have to maintain optimism to stay motivated when you have doubts, which will be all of the time. To maintain optimism, part of you has to fully believe in what you’re doing. But you can’t go all-in on self-deception when you’re tired of living with doubt, which you will be. If you stop being honest with yourself, you won’t notice quickly enough when you need to change course.

Number three, clarity. As much clarity in any given situation as you can muster. Your world will be constantly changing, so you’ll be constantly chasing clarity. But that’s actually your job: continuously identifying the most important problems while everything keeps changing.

Number four, perspective. Perspective on what’s important and what is truly worth being unhappy or stressed about. You’ll be unhappy plenty of times about plenty of things in your company. You don’t need to become the Buddha to get through it, but you do need to be able to recognize how silly you’re being when business stress causes you to neglect family and friends. If you found out tomorrow a loved one has cancer, you’ll get perspective very quickly. Try not to wait for that. You need your brain to be able to regain perspective on its own. You need to be able to wake up from your startup sleepwalk before life kicks you in the head. There are plenty of balls you can and should drop when deciding work priorities. You can’t drop the ball on relationships without harming those relationships.

And number five, purpose. This isn’t the same as perspective. Perspective is having the ability to wake up. Purpose is who you are when you wake up. You need to deeply know why you’re doing a startup. Most of us aren’t trying to get humanity to Mars. We’re just trying to improve the lives of people we love, make good use of the opportunities we have, live by our values, be happy, and generally be the best person we can be. Your company is going to be a major sacrifice for the next ten years of your life. If running your business doesn’t give you purpose or isn’t helping you figure out what gives you purpose, then you’ll run out of steam which in turn means your company will run out of steam.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

The most common mistake I’ve seen founders make is internalizing that same bad advice about data: thinking there’s some data they’re supposed to collect that’s going to tell them what to do.

If you’re a founder who’s not a data scientist, and honestly even if you are one, the key to not letting data take you down the wrong path is frighteningly simple: trusting your vision. That includes trusting your vision even if your vision is still being formed.

In the early stages of your company, the only thing you have that others don’t is your vision. That vision will change, but it should be driving your decisions when you don’t have significant revenue. If your company direction could be determined from the behavior and desires of a relatively small set of people who visited your site, someone else would have already solved the problem. Your job is to take your unique experiences, background, knowledge, and insights and use those to identify a problem you believe exists but that few others can see in the same way you can.

Understanding the relative value of your vision compared to small data sets will also serve you well when you get your first users. Your initial users won’t be representative of the majority of users you’ll have in the next few years. Your initial users came from very specific sources where you got a little bit of attention. What they need and ask for is important, but you have to train yourself to interpret their feedback the same as you would if you had 100 times as many users where very few others were asking for the same features. You’re the one who knows your vision and what you’re creating. It will actually benefit your early users if you keep your vision in sight so your company can be successful. It won’t do your first customers any good if you end up creating a mediocre company.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

To keep from burning out, you have to know what you yourself need to survive. It really is about the individual. You need to know what makes you happy and healthy and vibrant. For people like Allison, her happiness requires that she exercise and feel like she’s taking care of her body. That has nothing to do with being a CEO. That’s who she is. She understands that and prioritizes her physical health. Endurance sports are her mediation and revitalization. She needs it.

Each of our brains are different, though. Sure, if you’re not taking care of your body, you’ll burn out faster than otherwise. But if physical activity, for example, has never been your source of sanity, it probably isn’t now. Absolutely make yourself exercise once in a while regardless of whether you’re a founder, but don’t deceive yourself into thinking you can solve your happiness problems by finding more willpower than you’ve ever had and that you’ll do that while running a company.

Whatever gives you strength and refills your cup this week, in practice not in theory, that’s what you need to do. If it’s something you’re proud of, that’s awesome. If it’s purely for pleasure, that’s cool, too. Take it easy on yourself and pay attention to your own needs in the little time you have to reflect.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Allison and I like to talk about things like this over dinner. We like to dream and be creative together. It’s a sign we’re really on fire when we’re doing that regularly.

It’d be wonderful if nuanced thinking was culturally valued much more deeply. We all have biases and see the world differently than others. But when people have black-and-white views, it makes them easy to manipulate which is a big and arguably existential problem for societies to have in the age of the internet.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Definitely Ben Horowitz.

In terms of the insights and experiences of others that truly helped me over the years, his essays and his book, The Hard Thing About Hard Things, are at the top. He doesn’t pretend he has answers. He instead goes deep on real topics and painful situations, deep enough and real enough that others can find aspects relevant to their own situations.

When Allison took over from me as CEO, my favorite essay of Ben’s quickly became one of Allison’s favorites, too. That’s his essay about the most difficult skill of the CEO is managing your own psychology. I recommend that essay to all CEOs.

How can our readers further follow your work online?

The best place is the EarlyDog journal. For EarlyDog, rather than having a blog, we decided to keep a journal. We really value that we can go deeper on topics in work and life than one would normally find in a company’s blog. Making decisions like that is part of what’s great about having your own company and being able to intentionally create the culture you want to work in. Just like Allison and I continue to learn from each other after many years, we’re creating a company culture around learning and personal growth.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!