I wish there were a way to communicate it such that people could really feel it without going through it — but it is just so bleeping hard. It’s not classically, gruelling hard. There are so many professions that are harder physically and some that are even hard psychologically. But what I think makes starting a company so uniquely hard is how unexpectedly and completely it can collapse your work and self. The default path of a startup founder is to completely collapse how you evaluate your self-worth into how the company is doing.
As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Matt Martin.
Matt Martin is CEO and Co-founder of Clockwise. Before Clockwise he helped build RelateIQ, a company acquired by Salesforce for $390 million. He has previously been a front-end software engineer, a civil litigator, and a founder of a variety of software startups. He holds a B.A. from Dartmouth and a J.D. from UPenn in Philadelphia.
Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?
In elementary school I made hyper card stacks with Mac 2s. I loved the possibility of the computer. In school I developed an affinity for history and desire to impact systems at the highest level. Going to law school and then starting in Big Law, where you measure your time by the six-minute increment, gave me an appreciation for the preciousness of time.
So I left law and pursued a career in software engineering in San Francisco. This brought me to several companies, the most impactful of which was RelateIQ. That’s where I met my Clockwise co-founders.
We shared, and continue to share, a common goal: Giving our users more time for focused work, family, and friends. More time that matters to you.
Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?
I think the first lesson is just being comfortable in your own shoes. There’s just this innate impostor syndrome around not having credibility to lead the team. You start the company with a set of people that you know and have worked with before. But starting a company doesn’t change who you are. The expectation that it should do so is one that’s completely self-created — I think that most people who start on any endeavor create an expectation around, “I should be a leader now. I should be more commanding. I should act more like a leader.”
You compare yourself to leaders you’ve worked with, and that’s just not you. No leader you’ve experienced before is going to lead in the same way that you lead. It was a journey for me to get more comfortable in my shoes. I can’t say that I’m fully there yet. But, the self-acknowledgement that you’re going to lead differently than anybody else, and that’s okay, has been huge. You’ve got to find what works for you and meld that with what works for the company.
Let me give you a very small example: I used to really overthink investor communications. I would ask colleagues to vet drafts of an email to inbound and existing investors. In retrospect, that sounds hilariously overwrought. And it was. It got in the way multiple times because it would delay timelines. Asking three or four people to vet one email draft means it takes three to four cycles to actually send the email. That’s not effective. But it comes from this insecurity and this impostor syndrome around being the leader of the company and wanting to maintain that outward appearance. And once I became comfortable with who I am and my tone of communication I realized that I am more than perfectly capable of emailing investors and giving them responses.
What are some of the factors that you believe led to your eventual success?
I don’t know if you’ll ever really feel like you have full success. Look at Airtable, which has been around for eight years and is finally breaking through in this big way. People are like, “Wow, they really came from nowhere.” But they’ve been at it for eight years. That journey is really long and winding.
And, it’s kind of a meta answer, but the biggest thing that has led to my success so far is the realization that that success is a journey. It sounds really corny, but this is a marathon not a sprint. Your micro perception of where you are in the moment is often very misleading and will often steer you wrong about where you want to go. It’s really easy to focus on this bug that just came in or this customer who said this really awful thing, and you just can’t. You will not only run yourself ragged, but you’ll run your company ragged as well. It’s your job to remind the company of the big picture, stay true to the mission, and drive towards the ultimate destination, which is the realization of your company’s vision.
What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.
Everybody tells you this — and I wish there were a way to communicate it such that people could really feel it without going through it — but it is just so bleeping hard. It’s not classically, gruelling hard. There are so many professions that are harder physically and some that are even hard psychologically. But what I think makes starting a company so uniquely hard is how unexpectedly and completely it can collapse your work and self. The default path of a startup founder is to completely collapse how you evaluate your self-worth into how the company is doing. Doing that creates this exhausting emotional toll, and again, it happens by default; such that you have to thoughtfully work to remind yourself that you have individual value beyond your startup. That is something that is difficult to convey until you go through it.
Number two is related to number one: I wish people had given me a better toolset to manage my own psychology. There are countless blog posts (and some great podcasts: hat tip to Startup Therapy) on this subject, but it’s a very personal journey because it is a reflection of your own strengths, weaknesses, insecurities, and blindspots. Furthermore, it’s a tricky balance because, on one side, the drive that you need, the grit, the perseverance, the blind optimism, they’re required to power through some of the barriers. And yet, those same characteristics can take a nasty turn where you run yourself too thin. It takes a toll on yourself and the company, because you end up optimizing for perceived success rather than what the company needs. You end up going after what will make you feel and look better versus what is going to turn the team toward success.
The third is coaching. I’ve been working with a coach and it’s been really, really valuable. There’s part of me that resisted it. It just feels a little bit… coddled? Founding a company tends to attract people with a lot of grit and perseverance, but that can often translate into a resistance to focusing inward. Personally, I run these little narratives that are related to the above mentioned imposter syndrome: “who the hell am I to need a coach?” But having somebody to force outside perspective on you and guide you through thinking about your needs and how they relate to the business and how they might be the same and how they might be different. I think of it as an accelerant. You can get there on your own if you have the right peer group and the right mentors. But having somebody who just helps you focus through that, I can’t speak highly of it enough.
Fourth, I wish somebody gave me a set of peer founders right at founding. I want some sort of magical, “You’re starting a company” care package. “Here are the five other people who are doing it right now.” I was cognizant of that need and I did an okay job of cultivating some friendships with peers. And they’re just some of the most valuable professional relationships I have. The coach is helpful for giving you personal advice in a way that’s relatively intimate but peers are really helpful for working through contextual situations. Everything from like, “We’re onboarding a new employee for the very first time, what do you guys think about for HR software?” all the way to, “Dang we’re going through a macroeconomic environment related to a pandemic that is totally unforeseen and messed up. How are you guys helping out your employees?” Often as a CEO you’re navigating the unknown and making bets with massive amounts of ambiguity. Having a peer group to at least field those bets off and see how other people are making the bets is just incredibly valuable, all the way from tactical to the more existential.
The last one’s highly personal. Everyone’s got to find their own style of leadership. For me, vulnerability is an asset. You don’t have to pretend like you know everything. You don’t have to pretend you have the answers. You don’t. Your goal as CEO is to build up a team that fills out all the spots where a business needs strength and they don’t need to come from you. And they won’t come from you. And if you try to make them come from you you will massively fail. And so being open and honest about your limitations and where you need help isn’t just valuable, it’s straight-up a requirement. If you want to call that good delegation instead of vulnerability that’s okay. I think vulnerability serves to allow people to raise a hand to say “I wanna help.” I think that’s a much better motivating force than to say, “Hey I need you to do this thing.” However you say it, you can’t do it all yourself.
What advice would you give to your colleagues to help them to thrive and not “burn out”?
Find the ability to separate the short-term wins and losses and long-term wins and losses. If you spend too many emotional cycles down in the nitty gritty you’re just going to wear yourself thin. It gets even more complicated when you attach that emotional connection to it. I think that’s the biggest thing.
Another thing is, you need to make space to feel healthy. If the way you feel healthy is by taking a walk through nature, or by going to the gym and pumping out reps on a cardio machine, or if it’s going for a run or a bike ride, or if it’s just taking a walk and listening to a podcast, physical health, and giving yourself the space to pay attention to that, is really critical. And pay close attention to sleep. The number of people I see give up the long game because they wanna win the short game by not sleeping as much… you’ve got to find your threshold of how much sleep you need and live by it.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?
I’m really lucky in that the person I point to is Steve Laughlin. He’s one of the investors in our seed round and continues to be on our board today. He occupies a special position for me personally, and also the company, because he was a leader at the prior company I worked for. I looked up to him as a leader, I looked up to the guidance he provided. A specific example is hard because there have been so many over the past five or six years.
I’ll never forget walking with him and telling him this idea and him just stopping in his tracks and saying, “You need to go build this company.” It’s obviously very validating to get that feedback from someone you respect. What really stuck with me is the faith that he had that we could do it. By we I mean the founding team, but also that I specifically could do it. That I could lead a company to success. He had faith in my ability to execute and my ability to be a leader. Having been a CEO himself, he’s very founder-centric and very empathetic to the needs of the CEO/Founder. And he’s always been a good coach in my corner. He’ll give me really hard advice. It’s very akin to a coach where he’s not going to pull a punch, but he’s always going to be rooting for us to win.
What are some of the goals you still have and are working to accomplish, both personally and professionally?
We’re at a company that has early product-market fit. The demand for what we have is clear and to some degree the roadmap to what we need to deliver in order to expand the user base and expand the set of customers who can access our product and expand the scope of impact that it has is pretty clear. Now we need to build out the team that’s going to increase the capacity for the company. It’s a different set of thought processes than I’ve really had to engage on in the past. We’re still small enough that you can think about capacity in terms of the individual players on the team. But when thinking about expanding the capacity of the company beyond this stage, it starts to be about whether we have the leaders, functional heads, skill sets, and experiences represented on the team to uplevel the capacity of the company overall to address new challenges. For me, personally and professionally I want to focus on recruiting and retention of that leadership team — watching out for the people who will set the tone of the company overall.
What do you hope to leave as your lasting legacy?
What’s most important for me personally is the people I get to work with. My hope is that everyone who’s part of our journey at Clockwise looks back at this time as really personally rewarding, enjoyable, and valuable in their career. And, if I’ve done my job well, I hope that they look back on me as someone who cared for the outcomes of the team and the company. That’s what I want, really, is for people to have a good place, to be part of a mission that they believe in, and be able to build something with them. It’s not easy. Every single day isn’t always fun — and I’m not going to be loved every day! — but to look back and say Matt cared about the people, the mission, and the company. That’s all I can really ask for.
You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!
There are so many problems in the world that can’t be addressed by software. But, for the sake of the conversation let’s talk about software and where I can make an impact there.
I do think that there is an inevitable reckoning coming with regard to how people choose to spend their lives and how people are asked to spend their time at work. There are a lot of jobs out there that aren’t about self-actualization. But in knowledge work there are a lot of people who do get a lot satisfaction, purpose, and meaning from their jobs. It becomes a big part of who they are. I think that’s true of all workers. What I’ve noticed is that workers often don’t have a lot of control over how their time is spent. If we can help drive a movement that helps people actually decide how to best leverage their time, we can help them live a better day. Whether that’s in a software organization, marketing organization, in a factory — whatever it may be — we can help people have a higher degree of impact in their work life. That changes how you show up, how you feel in the morning, and the satisfaction you get from helping to build something through your work.
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