May 26, 2023

Radicle Health’s Former CEO, Tyler Hoffman on Stumbling Into Leadership and Why Every Great Leader Needs to Fail

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If you ask Tyler Hoffman how he approached an already impressive career at Alpine Investors and ASG, he’ll jokingly tell you he ‘inceptioned’ it. Starting out as an intern on the investing team at Alpine while he was still an undergrad, he’s since held investing, Chief of Staff, CEO, and Group CEO roles creating a track record of both results and fiercely loyal teams. 

As he ends one chapter as Group CEO of ASG’s Radicle Health and preps for the next one leading a soon-to-be-launched Alpine platform, he reflected with us on his career and what he’s learned along the way.

An Interview with former Radicle Health Group CEO, Tyler Hoffman

You’ve worn a lot of different hats during your time with Alpine, ASG, Foothold and Radicle Health — could you take us on a quick tour of your career here?

The headline is that my career has been defined by Alpine. I interned at Alpine on the investing team when I was still in college. When I graduated, I came back and officially joined the investing team for about a year and a half. The people I worked with were fantastic and the work was interesting, but I quickly realized that I had an itch to work in a company on the operating side. 

I was spending all this time interacting with founders and management teams and making pronouncements about their businesses. But I had never worked inside of a business and I felt it was important for my credibility — not just externally, but also with myself — to get experience on the ground. 

Everything aligned when Alpine acquired a business called Foothold in New York City, where my girlfriend — now wife — was living. Alpine offered me an opportunity to join the company, and I took it. 

Over the past five years, I’ve held various roles within Foothold and Radicle Health, the bigger human services software vertical we built on top of Foothold and other related acquisitions like KCare and Link2Feed. 

It's been amazing. I've learned a ton, and it's been equal parts hard and exciting. In short, I was able to scratch the operating itch, and then some.

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We "retired" Tyler's ASG & Radicle Health jersey earlier this year at our annual leadership summit as he preps for a new chapter.

While you’re moving on from Radicle Health, your next chapter will still be with Alpine. What is it that keeps you in the Alpine community?

I’ve built up a tremendous amount of loyalty and gratitude towards Alpine because of their unwavering trust in me, even when I didn't feel like I had earned it. They consistently placed me in positions I didn’t yet deserve because they had faith that I’d figure it out, even if I didn’t always have that faith in myself.

When I transitioned from the investing team to Foothold, I didn't believe I had any business making that leap. I was only 23, fresh out of college, still stumbling and learning along the way. Alpine entrusted me with a significant responsibility. Foothold was the largest ASG business at the time, and — at least in my own head — it seemed like I had the weight of the world on my shoulders.

Tyler Hoffman shares why he chose to launch his software CEO career with Alpine Investors and ASG.

Alpine has made it a core part of their DNA to continually challenge and push individuals within their ecosystem once they have enough confidence in them. It's an exciting environment for me to build my career, knowing that I will have an entire community supporting and pushing me in that way.

Another aspect I deeply appreciate is the quality of people within Alpine. I recently attended a CEO Summit in Austin, and a few weeks before that, we had an ASG operator retreat in San Francisco. 

Every time I'm in a room with fellow Alpine business leaders, it reminds me that we’re all going through similar experiences and everyone is genuinely committed to helping one another. There’s a shared humility and a sincere desire to support others in similar positions. The sense of community makes the job much more manageable and enjoyable. 

What surprised you most in that first leap from an investing role to an operator role when you moved to Foothold? 

There was definitely some strong cultural shock early on. I came in with such a strong emphasis on financial KPIs, metrics, EBITDA, and all the concepts that had been ingrained in my mind on the investing side. 

The problem was that my team didn’t particularly care about those things. They cared about making Foothold an amazing place to work, taking care of our customers and, in our case, helping our customers to take care of the individuals they serve. 

It took me a while to appreciate the "organ rejection," so to speak, of entering a business environment without understanding the language or vocabulary used by the people in that business. 

Eventually, I figured that out and I think I was able to play a valuable role as a translator between the investing side and the operating side. I deeply internalized and understood what Alpine and ASG were trying to achieve, while also grasping the perspectives of the individuals on the ground at Foothold. With some time, I started connecting the dots between those two things for everyone. 

Was there a specific a-ha moment where you realized you needed to flex to that translator role?

It was more a series of moments where I felt like people were looking at me as if I had two heads, in both the Foothold and Alpine settings. 

In the case of Foothold, I was conducting these deep dives into various KPIs early on. I created a mini curriculum to explain the KPIs we would be tracking in the business, how to think about them, and why they were important. 

While some people were genuinely interested, many others struggled to see the connection between those metrics and their daily work, which revolved around improving the lives and experiences of our customers through our software. I wasn’t effectively bridging that gap and illustrating the relevance of those metrics to their work. 

On the other hand, in the Alpine setting, particularly during board meetings, I would provide nuanced context about the history of our customers and the people within the business. In a board setting, these aspects didn't resonate as strongly. It's not that they didn't matter, but I was unable to clearly communicate the big picture amidst all the details. So, in both settings, I found myself not using the appropriate language for the context. 

Through trial and error I began to realize the critical role I needed to play as a value-added translation engine. As the CEO with insights into both contexts, I recognized the importance of ensuring that all stakeholders understood and considered the perspectives and concerns of the others.

Talk to us about the transition period from being CEO of Foothold to launching Radicle Health and taking on the Group CEO role. What were some of the shifts you needed to make between those two roles and mindsets?

The biggest challenge I faced was transitioning from wearing my Foothold hat to wearing my Radicle hat. Part of the difficulty stemmed from the fact that while I was running Radicle, I was also responsible for overseeing Foothold. 

In hindsight, I realize I should have made a more deliberate effort to establish clear boundaries and allocate my time intentionally. The inertia of continuing in my familiar role as the CEO of Foothold was strong, and without actively working to pivot and move in a different direction, it was easy to get caught up in it.

Another stumbling block I encountered was the transition from being a leader of people to being a leader of CEOs. It's a distinct shift in approach, even though it still involves interacting with and managing individuals. 

The experience forced me to prioritize developing my own management and leadership style, though. When you’re managing a group of CEOs you need to be comfortable with less detail. I came to realize the importance of empowering and supporting people to the best of my ability, and holding them accountable for results.

One of the hardest parts of coming into a CEO role is replacing a founder’s passion and sometimes decades of relationships and industry knowledge. What did you learn about that process during your time with Radicle Health, where you oversaw 8 acquisitions?

In my experience at Foothold, I was unbelievably lucky and privileged to have been gifted a founder who was just such a joy in every respect. Marlowe is still a close friend of mine even five years later. 

He was able and willing to put his ego aside and let me come in and basically take over his business. I still can't believe that he was able to do that. I was half his age when I started at Foothold, and I knew absolutely nothing about his business or the industry. But the posture he took was completely supportive of me. He gave me the benefit of the doubt early on and provided me the space to learn and make mistakes. 

It was a two-way street. I made it clear to him that I valued his opinion, and he made it clear to me that he was comfortable with me making decisions on my own. 

On the other end of the spectrum, we also had founders join Radicle who, while they were ready to sell, just had a harder time letting go of the business they built. I empathize with that situation because I’ve experienced it myself while transitioning out of a business I ran for the past few years. It's difficult to let go of what you've built, the team you've assembled, and the sense of importance you associate with it. 

Going through it again recently myself, I constantly remind myself of Marlowe, and it’s helped me keep my ego in check when moving on. 

You were spending more than half of your time in the later years of your role as Group CEO of Radicle looking for the next great business to join the group, and you’ve really defined what a hybrid investor/operator can look like. Are there a few key things you think anyone operating a business needs to know when it comes to M&A?

I wouldn’t frame the lesson here as people needing to spend time on acquisitions, but I think a core part of the CEO's job is to become an expert in their market. It's challenging when you're immersed in the day-to-day operations of your business to step outside of that and truly understand what's happening in your market from various perspectives — customer, competition, future trends, and more. 

Many people, including myself, tend to make the mistake of treating market expertise as an academic exercise. They create flashy slide decks or outline the total addressable market in an Excel spreadsheet. 

I learned and gained a deep understanding of the market by talking to people, particularly founders. The point I'm trying to make is that spending time on inorganic growth isn’t just about buying other businesses. Counterintuitively, it will make you better at running your existing business.

When you comprehend your market, including your position relative to competitors and the direction the market is moving, you can make informed decisions about positioning yourself. It could involve acquiring one of your competitors or another business to enhance your capabilities and competitiveness. Alternatively, it might mean doubling down on your organic efforts and becoming excellent at what you already do.

We talk a lot at ASG and Alpine about IQ, EQ and AQ being three things great leaders need to have. Is there a moment from your time at Radicle Health where you felt you really had to flex in one of those areas? 

Honestly, there were many moments that tested all three for me, with EQ and AQ being particularly important. And that’s not because I’m a genius; it's just that running a business is a deeply human endeavor.

The experience that truly pushed the boundaries of what I was capable of on all those fronts was COVID. I became CEO of Foothold in January of 2020, right before the pandemic hit. At that point, I had been in the business for 14 months and had made significant progress in establishing credibility and trust with the team. But there was still a long way to go. People understandably didn't see me as the leader of the business yet. 

COVID was the moment that allowed me to step into that leadership role by forcing both action and a clear articulation of  how much I cared about the team and our customers. Repeating that communication over and over again expedited the process of being seen as the CEO of the company.

Foothold is based in NYC, as were many of our customers and a large portion of our employee base — including me. In New York in those early months of the pandemic, it truly felt like the world might be ending. One small but tangible thing I did during that time was start an email chain with the subject line "Grateful and Confident" in late March 2020. In these emails, I expressed my gratitude for the team and my confidence in the future of the company.

Every Friday, at the same time, late in the afternoon, I would reply to the email with that week's version of the "Grateful and Confident" message. This continued through the summer. I would get replies from people, saying things like, "These emails really make a difference," or "It's great to know that we have a leader who cares about us and keeps us informed." 

Even though my message was more or less the same each week, and it wasn't particularly complex, it made a significant impact. It reminded people that I genuinely cared and hoped they felt the same way.

Coming out of that period, I truly felt like I was the CEO of the company and that I deserved to be in that position. People were also looking at me in the same way, as someone who deserved to be the CEO, and that created a big shift in my own mindset and confidence in leading.

Your next chapter will be moving back to Alpine to do this all over again with another company. What will you do the same and what will you approach differently?

The Alpine and ASG mantra of “People First" is one that I deeply believe in and care about. Initially, even though I had heard that mantra repeatedly, it seemed to me like you had to do all these People First things to ensure that people are happy, and then focus on what really matters, which is the business's performance. 

Former Radicle Health CEO Tyler Hoffman talks about the PeopleFirst leadership approach at ASG and Alpine Investors and why he believes in it.

However, I've come to realize that (as obvious as it may seem when hearing this) the performance of the business is actually just an outcome of how you show up for your team and customers. If you prioritize those stakeholders first, financial stakeholders will naturally be taken care of. So, People First is something I strongly believe in at my core, rather than just something you have to do. It was my mistake for not fully understanding its significance early on. In my next venture, I’ll approach it with even more intensity and proactiveness.

One thing I would do differently is to more clearly establish and communicate expectations from the beginning. Given the circumstances under which I arrived — being young, stepping in right after an acquisition, and considering the skepticism surrounding private equity and acquisitions in the industry, I was cautious about rocking the boat too much. 

I really leaned on the message that things wouldn't change much. People interpret your words quite literally when you're in a leadership position, though. While the spirit of the message was true, the reality is that things do change. 

We acquired Foothold because we saw its potential and thought we could help them tap into it, which requires making changes. In hindsight, I should have made it clear that we're not changing things just for the sake of shuffling the deck, but rather to improve and grow the business. My role is to listen, learn, and understand what should stay the same, but also what should change. In any business, there are many aspects that are worth changing.

ASG’s CEO, Steve Reardon talks a lot with our leaders about his belief that  ‘the CEO with the best team wins.’ What are some of the things you tried to build or really appreciated in your teams at Foothold and Radicle Health?

The thing that stands out with the Foothold leadership team is that there was a healthy balance of fresh outside perspective and deep-seated company and industry context and expertise. 

We established a cool balance where I could come in and say, "Hey, this might be a terrible idea, but how about this? Should we think about it this way?" 

Nine times out of ten, the company/industry veteran in the room would say, "That is a terrible, terrible idea. If you want to do that, go for it, but let me walk you through the five times we've tried that and explain why it failed. Then you can make your own decision." The perspective of an industry and company veteran saved us a lot of wasted time.

But one time out of ten, that person would react with, "Wow, that's a great idea. Here's what you should keep in mind as we implement it." That dynamic created checks and balances, and it was so fun to work in that environment. 

With the Radicle Health leadership team, we also had an interesting display of checks and balances, but in a different form. Each of us in the Radicle leadership team naturally gravitated towards a particular functional area of the business. Katie gravitated towards product, Alyza towards sales, Emily towards the customer's voice, James towards finance, and I naturally gravitated towards M&A due to my investing background. 

We all had the ability to speak the language of the others, but we were also responsible for educating each other on our area of expertise. This was nice because in a vacuum, each of us might have had some blind spots. Without the others, I might have solely focused on M&A and we could have bought businesses we shouldn't have or spent too much time on M&A instead of organic initiatives. 

The same could be said for everyone in their respective areas. But as a combined leadership team, we were able to operate as if we had strengths in all those areas. It was a strong example of the power of surrounding yourself with people who can address your blind spots by bringing different skills and passions. 

You’re well known in the ASG community for being a very transparent and thoughtful communicator when it comes to your team. Was that a muscle you built over the years, or is that just something that comes naturally to you?

I've always been very direct, maybe to a fault. I think early on, I was inclined to just state a decision and say, “here's what we're doing.” What I've changed in my communication style over the years is that I've become far more transparent about my thought process and the different factors that led to a decision. 

I usually preface it by acknowledging that not everyone may be interested in all the details and that some may disagree with the final decision. But I believe it's important for everyone to understand the thought process and be aware of the various variables we considered. 

Former Radicle Health CEO Tyler Hoffman on balancing directness and transparency in leadership communications.

In addition to helping people understand the context, I think it also helps them see that all of us on a leadership team are just humans. When we articulate that we're just people in a room, discussing different options, it resonates with people who constantly evaluate different choices to make the best decisions in their own lives and work. 

What are you looking forward to most in the next chapter? 

I’m really looking forward to building a culture from scratch. The reality of the situation I found myself in, and that many other ASG leaders find themselves in, is that they are dropped into a business that has existed and thrived for a long time. 

These cultures don't necessarily require significant changes. It's more about making adjustments at the margins. The foundation of the culture at Foothold and other Radicle businesses was already awesome and every new hire we made was an opportunity to propel the culture forward.

Nevertheless, I was placed into a culture that was already there, and I had to adapt myself to it while simultaneously guiding others towards the culture I envisioned for the business. It was a balancing act. 

What I'm really excited about is the possibility of starting from scratch and establishing norms with a small group of people. And then, maybe 20 years from now, when someone else is dropped into that business, they’ll inherit the culture we created. That will be their responsibility and they’ll struggle to reverse all the bad decisions I make! But I want to be the one to initiate and lay the foundation for it.

Sounds like the building phase is one you love?

I do. And that's ultimately what got me very comfortable with transitioning out of Radicle. It's built, the businesses are performing well, and the team is rock solid. 

There's still a lot of work to do and I realized that not only was I not the best person to do that work, but that I was surrounded by a team of people who totally were the best people to do it. My moving on opens up new opportunities for others on my team who have more than earned them.

Any words you’d like to leave us with?

I'll leave you with the same message I shared with the ASG team and CEOs at the retreat a couple months ago! The single most important thing that I'm currently learning, and it's a lifelong process, is that nobody is perfect and it's okay to fail. 

In these challenging positions that have various dimensions, not only is it acceptable to fail, but it's often necessary. You don’t make mistakes on purpose, but you will make them. And when you do and your team witnesses it, own up to the mistake and say, "I'm doing my best here. I thought the decision was right at the time, but it turned out to be wrong. I take responsibility for it, and here's what we can do differently next time." That vulnerability and honesty will help your team see you as just another imperfect, fallible human being doing their best.  For me, that’s been a crucial step in embracing leadership wholeheartedly.


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