5 Keys to Being a Great CEO

Author's Note: I realize self-funded, traditional, long-term hold, and accelerator vehicles each have a unique mixture of investors, natural mentors, banks, and board members. But this article is intended to be equally valid for all search CEOs. The key ingredients for success do not vary, since the central challenges you face are identical, regardless of structure. I am writing this article for all searchers, whether the Stanford Business School grad with all the right institutional backers, or ^redacted‌ in Salem, Oregon who last week wrote: "I'm incredibly proud to share that I've officially closed on my first acquisition The business is now 100% mine, and as of last week, I left my W2 to run it full-time. This took two years of grinding through the learning curve with no business school background, no Ivy League connections, and honestly, I didn't even grow up around business owners. Just me, a lot of late nights studying business fundamentals, analyzing what felt like endless deals, making plenty of mistakes, and refusing to give up. In competitive deals, especially when you don't have an existing business or deep industry connections, 90% effort doesn't cut it. You need 100% relentless execution and follow-up. I mean truly relentless - returning calls within the hour, having answers ready before sellers ask questions, being the person who shows up consistently and does exactly what they say they'll do. That's what ultimately won this deal over other buyers who had better credentials on paper." The world is changing fast, and the search ecosystem with it. Amidst this chaotic ecosystem filled with AI, billions in investment capital, and searches now literally across the globe, here are five keys to success as a search CEO in this environment for every Searcher walking into their first day on the job, from Salvador to all the traditional searchers out there. Aspen Grove on a hike near Sundance, Utah #1 Take Your Mental Fitness Deadly Seriously "What good is it to gain the whole world and lose your soul," one CEO recently told me. Mental Fitness is getting somewhat more attention, but not enough in my opinion. Being a first-time CEO is potentially the hardest thing you will ever do. It is a marathon, not a sprint. To succeed, you have to take your own mental (and physical) health seriously. That means being radically honest with yourself about how you are doing, having emotional support, knowing when to push and when to rest, and maintaining some semblance of balance. What I have observed way too many times is CEOs who gain 25 pounds in their first year on the job, who show up to board meetings looking like they got run over by a truck, and who are falling apart but think they have to white knuckle it, never admitting how close they are to imploding. Do NOT do this. It is not sustainable. It does not improve your chances of long-term success—exactly the opposite. You cannot make good decisions or lead people when you are not taking care of yourself. Everyone is different in this area, but the stress level is universal. Just have a plan before your first day on the job. Know what your non-negotiables are for stress relief (working out is mine, as is meditation). One CEO put it this way: "During tough times in my life, I would tell myself, 'At least I will always have the trees.' I'm most in flow when I'm hiking in the forests & mountains. I go through periods where I don't always follow my own advice, but my mental clarity and sense of perspective is always much better when I take a day each week to hike somewhere hard & beautiful. Since hiking is nearly free and I enjoy it more than anything, it really helps balance any nagging voices about financial collapse that any CEO faces. I think you need something to play this role in your life to counterbalance the risks that every CEO takes. Even if you lose everything, you will still have the trees." Know where your support team is that has nothing to do with your job. This support can include friends from school or your church, mosque, or synagogue, or a therapist if that is useful to you. But have people in your life you can blow off steam with and who care deeply about you, completely independent of how well you are operating as a CEO. Don't expect much sympathy from your board. "Mental health is getting slightly more attention at the board level," a CEO told me. "I genuinely appreciate when board members ask, 'But seriously - how are you doing?' That said, those conversations often stop short of going where they really need to go, quickly reverting to business - targets, budgets, strategy. I don't blame them; it's hard to step outside the shoes and responsibilities of a board member for that conversation." That CEO notes the importance of building honest, ongoing support with mentors and peers who aren't on the board and don't carry the same responsibilities. But he underscores the importance of putting your own oxygen mask on first before you do anything else. Remember that deep humility is a superpower for succeeding as a CEO and staying sane. As a friend who is a repeat CEO put it: "One flaw I probably share with many other CEOs is that I have a natural reflex to present the strongest version of myself to people I perceive as more accomplished. You have to appear impressive to attract investors, convince sellers, and win big customers. Since you start off these relationships from the standpoint of 'fake' strength, it can be hard to transition to a more authentic version of yourself, first, because it's hard to admit to yourself that you actually know very little, and second, because you're revealing that the strong self was a charade all along. I tried to project strength a lot in my first company, even though I didn't know what I was doing most of the time. In retrospect and with the benefit of maturity, I must have looked ridiculous. I can remember instances where my 'strong self' was making commitments to my board/customers, and my 'authentic self' was simultaneously saying in real-time, 'Why are you doing this, you have no idea what you're talking about.' This was a reflexive 'Fake it till you make it' which is so strongly encouraged culturally. I really try hard not to do that now, but I still catch myself occasionally." Over-invest in your mental health even when your brain is telling you don't have time. In the long run, doing so will allow you to perform 1000x better than the CEO who tries to be a hero while pile driving themselves into oblivion. "When I get too busy for personal time, I try to remind myself that Jeff Bezos doesn't take meetings until 10:00 AM and Warren Buffett barely takes meetings at all. If they can do it, so can I," advises a successful search CEO. Brown University Rowing Team (Cole Matlack in #2) #2 It's Always About Your Management Team A Great Team is crucial not only for being a great CEO, but, honestly, the most critical factor in determining your overall success. You are not that smart. Get brutally honest about what you know, and are good at, and what you are not. In most search acquisitions, you will build your team over time through trial and error as you assess what you inherited, gradually figuring out precisely what you need and can afford. But be aggressive. "Being creative and flexible also goes a long way," one CEO recently told me. "I hired the woman who would end up becoming the COO of my company, my most critical hire, when she was seven months pregnant. Most people would have skipped over her." Another successful exited search CEO gave me the following excellent summary of hard-earned wisdom he wanted to pass on to new CEOs about team building: • Early constraints demand creativity. One of the core challenges for search companies is limited resources or company size, which often makes hiring "true" C-suite executives unrealistic early on. That's where creativity matters. The ability to identify and develop athletes, people with the capacity to grow into larger roles, can become a powerful multiplier over time. • Leadership and mental health are tightly linked. A strong leadership team takes real weight and stress off the CEO's shoulders. A great team (like the one I had) feels like partners who fight with you in the trenches for a shared cause, not subordinates. That shared ownership makes the journey not only more effective, but also more sustainable. • Measure performance, but anchor on values. Performance should be measured constantly, but if you want to go far, adherence to core values must be measured with equal rigor. These are non-negotiable behaviors that underpin the company's culture. Sales can fluctuate for reasons outside the team's control, but behavior never does. Values should be the true north for hiring, firing, and performance reviews. • Customer trust is one of your key strategic assets. As CEO, spend as much time as possible with customers, and mentor your leadership team to do the same. Learn their processes, understand their pain points, and invest in delivering the best service you can. Customer-centric organizations are built from the top down, and the returns compound over time. Whether you are a self-funded searcher or a long-term hold founder with an impressive resume, I hear this last point a lot: put away the theoretical playbook and focus on what your team and your customers are telling you in the real world. "MBA Searchers err too far on the side of not really being interested in customer and default to 'strategy' rather than rolling up their sleeves and understanding why the business exists in the first place," another CEO told me. Three or four years in, your success will be determined primarily by the quality of the people who report to you. They need to be better than you are at their respective disciplines. Your role is not to do their jobs for them but largely to stay out of their way and enable their success through providing the vision, building the culture, and leading, not doing. "You need to identify talent that is 'way too good for you' at first and sell them on the dream," CEO ^redacted‌ told me. "Giving them a sense of empowerment and ownership both figuratively and literally (with PShares)." Immature CEOs are threatened by potential members of their management team who are smarter than they are. Great leaders understand their success—the flywheel of this whole thing, which makes it sustainable over long periods of growth into the unknown, is building a great team. The CEO's most important role is to create a culture where the management team loves their jobs, where the team is constantly improving, and through them, the mission and values of the company cascade down the organization. In at least two cases I was personally involved in, the CEO built a team they thought was great, and then faced an unexpected external threat to the company's very existence: in one case a rogue technology outage that took all core platforms down for customers over an extended period and the other COVID which caused a high tech on premise business to have to go remote in an environment with poor internet and power reliability. In both cases, the near-death experience was the turning point in the company's trajectory. A major challenge became a huge opportunity, as the management teams in place were capable of taking heroic measures to save the company. Once things finally returned to normal, they never looked back. "It was the scariest moment of my time at the company," one of those CEOs recently told me. "It genuinely had the potential to kill the business. But the customer-centric approach of our amazing team turned it into an opportunity to deepen trust and strengthen relationships. When shit happens (and it will), have the right people in the room." Offsite in Guatemala with ^redacted‌ and Juan de Dios Aguilar. #3 Belong to a Robust Peer Group. "Having different peer groups where you can share the top 5% and bottom 5% of life has been a huge help both personally and professionally," says successful search CEO ^redacted‌, now head of his ETA holding company, Amplify SG. Do not go it alone. The answers may very well be with the man or woman right next to you in the trenches who faced the same problem you had two weeks ago. Reach out to your peers to ask for help and to give help. Peer support is one of the most powerful positive aspects of the search community. Do not blow off the importance of having a relatively small group of peers (6-8 is ideal) who are going through the same issues and challenges you are. Many search CEOs find a peer group in YPO forums. These forums are great because they foster cross-pollination, helping you get away from the inside baseball of search and exposing you to CEOs across industries. Others build their own peer networks through business school classmates, geography, or industry footprint. "I'm a big fan of YPO," one successful CEO told me. "However, I'll also add a shoutout to EO (entrepreneurs' organization). Depending on the size of the business and the CEO's background, EO could be a better fit. For me, back in 2015, I tried on both and chose EO. I needed to grow personally much more than I needed to talk about generational wealth." Both YPO and EO do a great job of providing structure for meetings, presentations, and retreats. If your peer group is less formal than a YPO forum, invest the time to make it formal. Make it a real thing, not just friends you talk to when the shit hits the fan. Create a regular meeting time, take turns presenting a problem you have to the group, bring in outside speakers, and plan a retreat once or twice a year to get away and bond with time and space to talk through the deepest issues you are facing. One technology search CEO made the point to me that you can have more than one peer group: "Having a few distinct circles has proven to be what worked best for me. My EO forum was the space where I could share the 5%, across both business and personal topics, and receive honest advice from entrepreneurs in entirely different industries. Another circle consisted of search-fund SaaS CEOs, who provided much-needed tactical help and practical best practices drawn from their firsthand daily experience. A third group was made up of fellow search CEOs, offering support on more universal aspects of the journey: board management, investor communication, and the broader challenges that come with the role." These relationships are gold and will vastly increase your probability of success. Board of CCD with ^redacted‌ in Dominican Republic #4 Build a Great Board. "In my previous company, I thought I had built a great board, but it backfired on me. I now strongly prefer self-reliance. Self-funded searchers probably mostly feel the same way about minimizing outside influences with conflicted motivations," was one search participant's take. For sure, a terrible board is worse than no board at all. And there are situations that I have lived through myself where board representation follows the debt or equity capital, and you have to play the cards you are dealt, even if they suck. My point here is simply to be as thoughtful as you possibly can. You have more power than you think. At the end of the day, you control which deal to do, who you take as investors in that deal, and how to pitch to all investors in a way that best positions everyone to succeed. Many investors in the ecosystem are dying because they have too many investments and not enough board representatives. So, if you are strategic about your approach to board composition, everyone involved will respect you. Here are some considerations. • The smaller the better. Focus on quality over quantity. The best board I have been on recently had three members—the more board members, the more complexity, and the greater the chance of free riders. You want everyone deeply engaged. You might not be able to get away with three, but shoot for four, and don't go higher than five outside board members. • Everyone on your board should have a key skill to bring to bear. It could be industry, geography, HR, finance, or sales. But a bunch of generalists will help you the least. The more specific each board member's role is, the more they will be able to help you, and the better they will work together. • Every board should have an alpha dog, the chairperson, even if not in name. You need to know the one person you have to convince to get something done. • Everyone on your board must be deeply committed to your success and have the bandwidth to spend on your company. The more in-person board meetings there are, the better, and the more they get to know your team and your company, the better. • Pick board members you like as humans. This will matter when things get tough. Fighting is okay. But a baseline of trust and admiration is required. They all need to be committed to your development as a CEO. "If someone is difficult at the beginning, there are going to be even more difficult as the relationship progresses, and it's best to avoid them when the stakes are low," a CEO told me. "It's easier to spot the crooks than the cowards," he warns, but the cowards sometimes do even more damage. You may not be able to achieve all five of these board elements, but see how many you can put in place, and I guarantee your probability of success, and your life, will be vastly improved. "It is tough to get investor attention, and the attention you do get is quite limited. The biggest thing I am taking away from the early days of my search is that I need to start thinking now about how I build a board," a searcher recently said on this topic. A recently exited traditional search CEO (I realize that self-funded searchers will have a different dynamic here, often with an SBA-backed bank involved, etc.) had the following twist on my board elements: "I agree that each board member should bring distinct, valuable skills. I look at those skills coupled with a slightly different lens: • An experienced search investor — someone who has seen your exact situation dozens of times before and can help you normalize issues, spot patterns early, and avoid common traps. • A recent operator — close enough to the trenches to provide hands-on support in the early years, with fresh experience in operations, running board meetings, and managing investor communication. • A large, reputable investor — capable of helping move material capital decisions, such as additional fundraising or returning capital to investors. This person often also plays the role you later call an "alpha dog." Obviously, in many cases, there is an overlap between those roles, and together, this mix creates a board that is not only supportive but genuinely useful when it matters most." Climbing 14k Pike's Peak with Tom Macejko #5 Find the Right Guide [Author's Note: of my five keys, this one got the most pushback when I previewed with readers as not being realistic. Yet, to me, it is central to everything. I have collected a wide variety of mentor stories from successful CEOs, from one of the original searchers to the CEO and Co-founder of Skratch Labs, in the appendix below for your consideration. One size does not fit all, but please consider what all these CEOs say on this point.] When ^redacted‌ approached me to invest in his search, I agreed to a coffee because I was skeptical. He answered the questions I fired at him well enough that I decided to try to help. I got Will Thorndike on board and then Pacific Lake. Soon his traditional search was done, and it was time to look for a company in the Dominican Republic as the first Searcher from Yale SOM and the first Searcher of any kind in the DR. A year later, Kalil found a call center business he wanted to buy. I helped him write the memo and raise the money. We met at Yale, where we both spoke on a panel just after the acquisition. Kalil was flush excitement. But a week later, he discovered that our company wasn't making money, it was burning cash. FAST. And our sales backlog was smoke and mirrors. He was presiding over a house on fire and, as a green CEO, had no idea what to do. What followed was panicked phone calls, a weekly flash financial scorecard (with an emphasis on cash to stay alive), and impromptu board calls. All the happy talk had to stop as I guided Kalil on how to build the information systems he needed to reach rock bottom, stop the bleeding, and start rebuilding from scratch. It would take eight years of meetings, phone calls, and 10k emails between the two of us, with numerous near-fatal experiences for our company, before we eventually exited the business for 6.5x the last moment before AI gutted our industry. Kalil ugly cried at the closing dinner. So, did I. I was so proud of him. And our journey meant so much to me. (See: https://www.linkedin.com/pulse/radical-love-board-room-tom-matlack-zzase) Who can you call when you realize you aren't going to make your numbers, you have a disturbing HR situation, or there's a devastating problem in your company (or your life) that you haven't told your board about? I am not talking about your CEO coach, your priest, your AA sponsor, your therapist, or your personal trainer (though you probably should have one of each of those, too). Your mentor is a person who has deep knowledge of search and operations, who is your primary teacher, someone you trust with your life, who you know in your soul can teach you how to be a great CEO, who always tells you the radical truth, who is harder on you than anyone else, and who loves you unconditionally. And who will drop everything to take your call. You can think of it as a river guide to being a CEO, and to your life. "You consistently reference unconditional love in your writing," a CEO told me yesterday, directly challenging my core advice. "I'm also skeptical you can build trust like this with a third party quickly. The only people I would trust at this level are a handful of family members who have proven it over my whole life, but they don't generally have the business chops to mentor a CEO. In my 20s, I trusted that my older business friends too easily and got pretty badly burned." I realize that my harping on unconditional love is unorthodox and may sound unrealistic... it is, in fact, a radical point of view. And yet it has made all the difference in my life. Yes, I spend most of my time mentoring people in business, in recovery from addiction, and my students, in most situations where I have no financial gain. And even when I have had money at stake, frankly, it's the last thing I worry about. My last big fight on a board was at exit because I insisted that the CEO get full economics. In my experience, financial reward is a by-product of love and passion, not the other way around. "How can the average Searcher find a new investor, or just a guide, whom they could trust that they haven't known for their whole lives? Having a mentor is great in theory, but how can you really trust they have your best interests at heart, especially if they've got a financial conflict of interest?" I was asked recently. If there is a financial conflict—if your guide is motivated by greed rather than concern for you—you absolutely have the wrong person. I am talking about someone mature enough, whether they are 30 or 70, that they understand the concept of sympathetic joy, that by helping another human at their moments of most profound need will bring more reward than making a few more bucks themselves (when likely they have enough already anyhow). If you ask the most successful CEOs in our ecosystem, they all talk about the special relationship they had with an investor, coach, boss, board member, professor, or more experienced CEO. To run the gauntlet of learning how to run a company—a gauntlet that becomes exponentially more complex as your company grows—while living your life, is a vast multi-variable problem. Why would you not find someone who has done 95% of what you are trying to accomplish and confide in them? A bad mentor is a shitstorm. A good mentor will change your life, and your family's life. It's worth trying to find one. To be clear, your mentor could be a board member and/or an investor, like I was to Kalil, but they don't have to be. I have played this role for CEOs, both on the board and off (in most cases, it was easier for me off the board). "Sometimes the most impactful mentors aren't always the 'gray-in-the-beard' archetype," CEO ^redacted‌ ‌says. "In my experience, mentors who are just 2-3 years ahead of me in the journey have been incredibly powerful. They've recently navigated the same challenges; their advice is highly relevant, and they still vividly remember what it feels like to be in my shoes. Some of the best 'mentors' blur the line between mentor and peer." Somebody needs to have a 360-degree view of you as a CEO and human being. I admit that finding the right person takes time and effort. But it will absolutely not happen if you aren't willing to trust anyone and are determined, as I was to my great detriment, to tell the world off, trust no one, and figure out every single thing on my own when it would have been so much easier, and in fact more meaningful, if I had allowed myself to have some help. High Camp Hut at 11,000 feet Final Thoughts Being a search CEO is different than any other CEO job in one crucial way: you have never done anything like it before. You are drinking out of the fire hose, learning on the job with investors, employees, maybe a bank, breathing down your neck. These are all strategies to deal with what, for months or perhaps even years, will feel downright impossible. Every Searcher since the beginning of time has felt the same way you will when you walk into your company on the first day as the boss. Being a great search CEO, like anything in life, is seeing opportunity in personal failure—having a growth mindset where the toughest thing you have ever faced can also be the best, most life-affirming, and most profoundly meaningful in terms of personal growth. "I was the young CEO who got thrown in a well and left for dead," a now-leader of a thriving company told me. "You need to believe that you are only in the first act when you experience failure. If I had believed life was just a series of accidents, I would have quit then. You have to have an enormous amount of faith in some meaning in your suffering to keep moving forward." Every successful search CEO I have ever met has gone through the valley of death, when you are handed the keys to the car with no driving instructions whatsoever. Everything I have written here is my, perhaps misguided, attempt to give you a manual before you get behind the wheel. In 2026, it is very easy to feel there are too many searchers out there, that it's near impossible to get the attention of investors, peers, and indeed anyone who might be a mentor. Technology might help you search or even run your company. Still, it also greatly accelerates this process of de-humanizing the experience of being a search CEO in a sea of capital. One CEO who is a thought leader in our ecosystem put it this way: "I've had bad experiences with boards and haven't had any luck finding peer groups or mentors. We spent our first year after business school chasing advisors and mentors that went nowhere, and we only succeeded after moving away from all the noise and just focused on the business and our customers. Sometimes I feel that I'm leaving something on the table, sticking to what is working and what I know. But a bird in the hand is worth two in the bush. And the enemy of great is good. Finding a business and investors is hard enough. I suspect that many CEOs like me see finding a mentor as a distant third priority, like eating more vegetables. Everyone knows they need to do it, but few people take action. Myself included." Sure, I get it. In 2026, in the mass of capital and chaos of AI-generated noise, everything I have said may seem impossible. But I want to double down on its importance. That is not to say you can't go it alone and try to figure out all this stuff on your own. But what you need to learn has been done repeatedly by the people you should have on your board and who you could find as your mentor. Most of what you are struggling with is not new or even that hard; it's just new and challenging to you. Don't get defensive, get help. The biggest mistake I made over my 30 years as a big-company CFO, a venture-firm founder, and a search investor is that I never once asked for help. I never really had a business mentor. When I was the CFO or the managing partner, I inherited dysfunctional boards. The whole reason I have devoted the last decade of my life to being a mentor is that I never had one, and I regret it deeply. Absolutely do NOT do what I did, which was stick my head in the sand and give the world the finger, on some crazy solo mission. Yes, it is harder to do these five things. But my argument is that AI, capital, and chaos make taking care of your own mental health first, then making the face-to-face human connections that will determine your success or failure, that much MORE important. I am with one of the founders of the search ecosystem, who recently told me that not only do great deals compound over long periods of time, but so too do great relationships. And the two things go hand in hand. Or as a first-generation searcher, put it to me: "You need to invest in building these relationships long before you think you 'need' them. Search used to always be first and foremost about building relationships with partners who would support the entrepreneur throughout the journey, with a willingness to deliver all messages that could increase the likelihood of their success (not the "nice" messages). In the current environment, too many searchers start with a transactional mindset, wanting to understand what a partner is willing to do." This approach is the opposite of long-term relationship building. "Building relationships, early and with sincerity, is a fundamental component of what drives success in the search model. Be quick to take feedback and course-correct based on the depth of the relationships you have built. A key to our success way back then was that we had the humility to know that we didn't have any experience doing what we were doing." A new entrepreneur who recently launched his search, perhaps four decades after the first generation, echoed the sentiment: "My prediction is that simply doing a search deal in the second half of the 2020s will not automatically grant you access to the search community; you are going to have to put in real effort to get yourself connected. I personally am going to be more intentional about reaching out to investors on my cap table and the ecosystem in general to try to build better relationships." Amen, brother, amen! Sunrise at High Mountain Hut Appendix: Mentorship Stories "My most significant mentor relationship started when I was 26 and continues today, albeit in a different form as he is mid-70s and we're just good old friends now. He was Chief of Staff to the Governor of Maine, and I was the Governor's Personal Assistant. As a result, there's a ton of overlap, and we became close. He then hired me out of b-school to be controller for a significant energy development project (Atlantic Energy, @ Cianbro). He left, and I stayed, only for him to hire me again to move to CA and take some Mainer-isms there and run the West Coast for his next gig (The Jackson Lab). When I raised a search, he bought a 1/2 unit but didn't invest due to conflicts, as he was on the JAX board. I've been to his parents' funerals, he's been to both my weddings, one wife's funeral, and I've been to all his kids' weddings. He knows me as well as anybody and has seen me do it all, helped me think through getting in and out of search. Mostly, he has the long-term through-line perspective on who I could become, who and how I became what I am. Different than a parent, who's gonna love you pretty much no matter what. The mentor can turn the page quickly in a convo and say, "Remember when you *ucked this up" or point you right back to values. A parent would probably be too soft. Or forget that you forget values even sometimes, too. I'm lucky to have him in my life." -^redacted‌, exited search CEO, now investor "I was working for a long-distance company in Rochester, and one of the founders was intensely bright and understood how their business ran (the nuts and bolts) and where the opportunities within the industry were to exploit and drive margins. I was thirsty to learn, and he was the teacher. He set up a meeting with me for the first time, but he was casual about it; no email to confirm, nothing. I'll see you Wednesday morning when I arrive. I was late, and he was pissed and chewed me out. From that point on, I busted my ass not to disappoint him. He taught me like a grad student. He taught me by example. He taught me by taking risks on me to see if I could solve the problem at hand. He followed my career after I left the company. I hired him as a consultant to help clean up some networks at the new business, at which time he offered me the job of being his number 1 at a company he was starting in NC. I turned him down after just moving my family. That was the biggest swing-and-miss event of my working life. Our relationship continued even though we were competitors at various times." -Kevin O'Hare, Telecom CEO "I don't exactly resonate much with the term mentor - perhaps early in my career - for some reason I don't think of myself as mentoring people or vice versa. I think of mentors as people who teach you a trade. By that definition, one key investor and board member did teach me details of sales - attended and ran our sales meeting every week for a year- that was huge. I had a friend of over 20 years who has played a unique role in my life as sponsor, investor, advisor, and most present, one of my top 5 friends that I talk to weekly. He is the only person who has direct experience in all the major worlds of mine - investing, search, and AA - so lucky to have that overlap - I would not know how to describe that to a CEO. I don't think many people can replicate that dynamic." -Successfully Exited Search CEO in Technology "I've always thought about it as a team of mentors / personal board of advisors… but if I had to pick one 'anchor mentor,' it's one board member + investor I've known for over 10 years, basically since I began my search — even before, when I first pitched him the idea. What makes him unique is how well he balances roles: he listens like a family member (he literally calls himself my "unofficial uncle"), but he also stress-tests my thinking like a serious investor. He'll first challenge the idea until he believes it… and then, once he does, he helps me think through how to land it with the other investors and navigate the board dynamics. In that sense, he's been both a mentor and a bridge—a calm, efficient communicator between me and the investor group. On a practical level, the way we work is simple: he'll invite me for a brisk morning walk around his country club, we talk through whatever issue I'm facing, and then we sit outside and wrap it up. Early on, it was more tactical (governance, structure, board materials — he always pushed me to be thoughtful and send pre-reads). Over time, it's evolved into more of a personal relationship where we talk through leadership judgment and messy situations. I'm sure he'd say he's 'graduated' me at this point — but I still get a ton from those conversations." -Successful Search CEO in manufacturing "I don't think I've had a single mentor in my CEO life. Instead, I've had different approaches at different times. At some points, there was a single person, but more often it was a small group of people or a small number of individuals who were driving my improvement. That said, my "full life" has had a single mentor who has spanned over 30 years and has been instrumental in shaping everything I am. Brian White was my ski coach when I was 12. Over the next few years, he guided most of my off-snow training and, more importantly, helped me start to grow up. At 17, he put me in my first bike race. At 19, he helped me navigate dropping out of college to go bike race more. At 21, he helped me win a national championship. At 27, he helped reset after an injury, return to college, and refocus. At 28/29, he helped me move forward with conviction in business as we were just getting started (and he knows very little about "business"). It's remarkable to think back on how much of my life has been influenced by Brian (and his wife Susan, who was a much better 'on-snow' coach!). I still talk to them. I know their kids (and even offer my own mentorship to them!)." -Ian MacGregor, ^CEO and Co-founder of Skratch Labs "Irv Grousbeck‌‌. Irv was the person who created awareness that an entrepreneurial path was available to me (obviously, the search path). He spent endless hours with me, educating me on how to execute it successfully. He wrote the largest check in my first deal, was the de facto lead director, and was fully committed to my success. He was never afraid to deliver difficult messages to me, but those came with the foundational knowledge that he was always available (I spoke to Irv at least once a week for the entire 4.5 years of my first deal). He played the same role in my second deal, which went horribly (we lost $50MM of equity), and was the one who raised his hand to deliver the message that the board had decided to bring in a turnaround firm and that I would be transitioned out. After that experience, he immediately agreed to support me again as I wanted to take a third pass at the search process. Over the past 35 years, Irv has been at my side, fully supportive, which doesn't mean blindly supportive. He has been a second father to me (and I am close to my father and love him dearly, so this is not a comment about filling a hole in my life). I wouldn't be where I am today (wherever that is) without Irv." -^redacted‌, 3x search CEO and founder of Anacapa