The Journey From First-Time Founder to Board Member and Mentor with High Alpha's Scott Dorsey

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This is a podcast episode titled, The Journey From First-Time Founder to Board Member and Mentor with High Alpha's Scott Dorsey. The summary for this episode is: <p>Today's conversation is with Scott Dorsey, Managing Partner of High Alpha. High Alpha is a venture studio that launches, scales, and invests in enterprise cloud companies, Casted being one of those. Not only is Scott a Casted board member, but he is also a partner and mentor to our host and CEO of Casted Lindsay Tjepkema. Today, he shares what it was like being in Lindsay's shoes when he started ExactTarget and what it's like coaching other industry leaders as he continuously grows as a leader himself. </p><p><br></p><p>Key Takeaways:</p><ul><li>A look into starting ExactTarget 03:53 - 06:40</li><li>Components of a great CEO - 12:38 - 13:47</li><li>The shift from CEO to Board Member/Advisor - 19:37 - 21:10</li><li>27:10 - 29:26 Three things to look for in a Founder - 27:10 - 29:26</li><li>32:42 - 33:40 Common challenges of first-time Founders - 32:42 - 33:40</li><li>35:28 - 36:45 Why you should have coach - 35:28 - 36:45</li><li>Make sure you have fun - 37:22 - 38:36</li></ul><p><br></p><p>Related Resources:</p><p><a href="" rel="noopener noreferrer" target="_blank">Scott Dorsey's LinkedIn Profile</a></p>
A look into starting ExactTarget
02:47 MIN
Components of a great CEO
01:08 MIN
The shift from CEO to Board Member/Advisor
01:33 MIN
Three things to look for in a Founder
02:16 MIN
Common challenges of first-time Founders
00:58 MIN
Why you should have coach
01:17 MIN
Make sure you have fun
01:14 MIN

Lindsay Tjepkema: Is it possible to be a first- time founder twice? And what's it like to start and grow a unicorn, and then attempt to do it all over again, but with a completely different business model? And how about serving as a mentor and trusted advisor while also stepping out into the unknown yourself? Welcome to Casting a Vision, I'm your host Lindsay Tjepkema. I'm a B2B marketer turned first- time CEO and founder at a marketing technology SaaS company that my co- founders and I named Casted. If I have learned anything in this role that I'm in now, it's that it's unique, to say the least. There really is absolutely nothing else like it. It's all about getting really nice and comfy cozy with being uncomfortable. And while you're out here in the wilderness charting a new path forward, there is so much richness in the experiences of others who have done it before. And if anyone has done this before, successfully, it's Scott Dorsey. He's currently managing partner of High Alpha, a leading venture studio that launches, scales, and invests in enterprise cloud companies, including Casted, where he also serves as one of our board members. But, prior to High Alpha, Scott co- founded ExactTarget and led that company as CEO and chairman from its startup to global marketing software leader. ExactTarget went public on the New York stock exchange in March of 2012 and then was acquired by Salesforce in July of 2013 for$2. 5 billion. Billion, with a B. But post acquisition, he led the Salesforce marketing cloud, which encompassed 3000 employees around the world. So in addition to all of that, Scott has somehow found the time and the mental bandwidth to be a truly incredible partner and mentor to me. I am so very eager for you all to listen in on our conversation as he shares what it was like when he was in my shoes, as a first- time founder and CEO, and how he both grows leaders and how he grows as a leader himself every day. It's such an honor. I'm so excited to have you here. It feels like it's about time, two years later, to finally have you on a Casted podcast show.

Scott Dorsey: Yeah. Thank you, Lindsay. I'm honored to be a part of the program. Thank you for having me.

Lindsay Tjepkema: Yeah. There's so much that we could talk about. You've really been a part of my leadership journey. You've been a part of Casted's story: as a board member, as a true partner to me and to the business, as an investor in High Alpha. So there's so much that we can dig into, but I really want to focus on the leadership story, and your leadership story, because there's many dimensions there. So, of course, you were a founder of ExactTarget and now of High Alpha, so I would love to rewind. If you can go back in time to when you were where I and Casted is now. So just post series A, fast growing company, so much potential, so much excitement, but also you had perfect knowledge of where you were and where you want it to be. Tell me what that was like for you, first- time founder for a really fast growing company. Go back in time and fill me in on what that was like for you to be in this seat.

Scott Dorsey: I'd be happy to, Lindsay. I was 33 when we started ExactTarget. First- time founder... Really, first- time CEO, didn't have a technical background, so I was jumping in, probably much like you felt over the last couple of years, learning so many things in the early days of building a business, and really growing and developing as a leader. I'd just finished graduate school, I went to Northwestern Kellogg, and earned my MBA. That was a really useful experience for me. I had three years of thinking about entrepreneurship and studying first gen internet business models and learning about technology. So this was a path I really, really wanted, and I was really committed. I had a number of leadership experiences throughout my life, in high school and college and then early chapter of my career, so I felt like I could be successful as a leader, but you don't know. Jumping in as a first- time founder and CEO... I always like to use the phrase, I didn't know what, I didn't know. I had so many unexplored areas that I just had to learn about, and for me, the key was both hiring a phenomenal team that I could learn from, and they could push and challenge me as much as I would pushed and challenged them, and then having the right mentors and advisors. We raised our series A from a phenomenal firm in New York, Insight Venture Partners, and they had 50 or 60 portfolio companies that looked just like us. I was really eager, not only to learn from the Insight team, but build those peer- to- peer relationships, meet those other CEOs that I could learn from. I'll tell you one of the nicest compliments I received, Lindsay, is they later reflected that I attended more of their programming than any CEO they'd ever worked with. And for me, it was natural curiosity, but also acknowledgement that there were just so many things I didn't know. So my strategy was I attended all of their CEO programs and workshops, but I also attended every program they had built for a functional leader. So I needed to learn as much as I could about engineering and software development, and they had a program for software development leaders, CTOs, and I attended that one with my CTO, so we could learn a common vocabulary and we could learn alongside one another. Then I would do the same thing for sales and go- to- market or professional services or all the different programming. In many ways, I think a CEO needs to be a generalist. You need to be well- versed enough across every dimension of the business that you can ask the right questions and know how to stitch those different parts and pieces together. And for me, our series A investor, Insight, they had a phenomenal platform in which I could learn and grow and develop.

Lindsay Tjepkema: I can absolutely relate to that. I mean, I say all the time to you and to everybody else, being in this seat, first- time, fast growth, is just getting used to being uncomfortable. It's just finding comfort in uncertainty and saying," Okay, if things start to get too comfortable or too clear, something's wrong. I need to start branching out to get a little more uncomfortable." But what was that like? ExactTarget was such a success story. I mean, everybody in and around SaaS, and in and around marketing, and of course here in Indi, knows it well, but you lived it. You were in this seat at the time before you knew what a success story it was going to be. What were some of the things that kept you up at night and some of the things that you felt most uncertain about when you were in these shoes?

Scott Dorsey: Yeah, sure. No, absolutely. I had a lot of vulnerability, Lindsay, of just wondering, am I the right person to lead the company and can I grow and develop as fast or faster than the business? Can I continue to grow in a way where I'm going to be the right person to continue to lead the company? A couple little stories I'll share, when we were getting started, we had three of us that founded ExactTarget: me, Chris, and Peter, and we kind of agreed that I would, ultimately, lead the company, but early days we ran it very much like a partnership. I wasn't even comfortable taking the CEO title so I made up the title of president and said," I'll be CEO one day, if you feel like I've earned it and I deserve it and I've grown into that role." That first evolution, as a co- founding team, is you really do run the business more as a partnership. One person needs to be in charge to ultimately make decisions, but it's highly collaborative and very partner oriented, which is my natural style anyway. Over time, as you get bigger, the need for a clear leader and a clear CEO becomes evident. I was happy I could grow into that role, but even raising the series A, Lindsay, I was very intimidated by Insight. I remember signing the term sheet, I was on fifth avenue in Manhattan with really, really smart, experienced investors in Insight, and I wasn't sure I could do it. I wasn't sure if I was maybe signing away the loss of my job if six or 12 months later, they didn't feel like I was talented enough or the right person to, ultimately, lead the company. But thankfully, I think staying humble and curious and a little vulnerable is the right approach when you have so much to learn and you just need to surround yourself with people that make you better. Then also, and I'm sure you've already felt this in two years at Casted, Lindsay, but you end up feeling like you have different jobs all within one job or you have different chapters to your story where you have to evolve differently as a leader. Early days, as I mentioned, it's hands- on, everybody working together, very partner and collaborative. Over time, you have to get comfortable delegating and hiring people that know way more than you do about their given discipline and empowering them and giving them the framework and the tools to be incredibly successful, and then you have to keep elevating as a leader. All of a sudden, now you're managing managers and you have to keep elevating as a leader and really understand where you can have the biggest impact on the business and what does the business need from you? Also, what's your leadership style? That'd be a fun topic for us to explore, but there's no one size fits all leadership style. You have to know enough about yourself and enough about the organization you're leading, to leverage your strengths and develop your own approach.

Lindsay Tjepkema: It's very true. It's very true. It's so great and so refreshing to hear you talk about how scary it was and how uncertain it is, because it truly is so unknown, which is part of what makes it so exciting. You told me, and the other partners I have will have told me, when we got started," Look, this company, this culture, this job will be what you make it," which is so hard to receive until you're in it. But it's so true because the entire team that comes around you — I also have two co- founders who are wonderful and we compliment each other really well — and then as the team grows, it truly is based around how we started and what we need around us to make us and the company and the team better. It is really interesting how those roles change because, like you said, you get started and you're in it, you're all hands on deck all the time, doing all the things, and with each milestone — we talked about this too — things change so much. Like I could feel, especially with each seed round and then the series A, I can feel the job description changing and getting pulled in a different direction. Another thing that you've coached me on, is that there'll be a lot of people in your ear. I think, CEO, founders, I think this is also true for senior leadership, that especially more successful you are, the more people are going to come alongside you and say," Hey, here's what you need to do. Here's where you need to go. Here's what you need to implement. Here's who you need to hire." How did you, specifically, weed through and sift through what to receive and what to say," Thanks, not a fit for me or for what we're doing." How did you do that over time? Have you continued to do that?

Scott Dorsey: That's a great topic, Lindsay, and you're so right. Even thinking about your allocation of time now that you've raised your series A, it's different. Your board of directors is larger, you've got more governance, more structure, you have more investors that you need to keep apprised of how things are going in the business, and hopefully pull out the very best of what they have to offer. So being eyes wide open around how your time allocation is going to shift and how you're going to be able to shift more responsibility to your team, that's the key, I think, to growing and evolving and scaling. I find the best CEOs — and I a hundred percent put you in this category, Lindsay — are both curious and coachable, but also have a very strong point of view. You don't want to have such a strong point of view that you're not coachable, but you also don't want to be so coachable that you say yes to everybody, and you don't even have a clear vision that's yours, that you're casting for the company and for the organization. So I think the best CEOs have both: they have a very strong point of view and a vision, but they're open- minded and they're coachable and they're open to feedback. I actually just had a 45 minute conversation earlier today with a CEO of a very large company and he just drilled me with questions for 45 minutes. Just wanting to learn, just curious about some of our experience at ExactTarget, and hopefully could pull a couple of nuggets away that might be useful for him. So I think you can always learn, at any stage of life and any stage of growing the company. Now, which voices do you listen to? That's a really, really good question, Lindsay. I would say where I ended up growing and evolving with my board was I had an extraordinarily talented board, but they were talented in very different ways, and diverse in the skillset and experience they brought. So I had, for example, one board member who was lights out in strategy. Any strategy topic, he was my go- to board member. I had another board member who was very gifted in M& A, and I was thinking about M& A pipeline and how to do acquisitions successfully, that was who I went to. I had a different board member who was airtight on governance and protocol for running a board and how to think about managing risk, and et cetera, et cetera. So I think it's useful to think about your advisors, your personal board of directors, your company board of directors, and think about, do you have specialists where you have two or three topics or two or three areas where they become the go- to person that you probably listen to the most?

Lindsay Tjepkema: That's super helpful. How long did it take you to wrap your head around that?

Scott Dorsey: It took me years, I would say. It definitely didn't come early, didn't come overnight. I remember hearing a program talking about your personal board of directors and that impacted me in a big way also, and the concept is: all of us have, or should have, a personal board of directors. Who are the six to eight people in your life that love you, care about you, and have your well- being in mind, and are your sounding board in life? It's a great exercise to write down," Who is my personal board of directors?" Then even better, to let people know," Hey, you're on my personal board of directors. You're that close to me and I care that much about you and I know you care about my well- being, that I think of you as my inner most group of advisors." People are generally flattered and blown away by the concept. But it's just being really thoughtful about how do I build a diverse group of advisors that can help me and help my company, but all in unique and different ways because you don't want... That's the definition of diversity, or lack of diversity, is you don't want five or six people that are all experts on the same topic. Having the range and the breadth is really important.

Lindsay Tjepkema: Yeah. The personal board of directors really resonates with me too, and you know that I love Brené Brown, she's my best friend, she just doesn't know it yet. So she has this thing where on a one inch by one inch piece of paper, write down the people that actually matter because it's also easy to start to get consumed by all the people that you feel like their opinion matters, because everybody's going to have an opinion about what you're doing, what you're doing wrong, personally and professionally. But if you can narrow that down to a small piece of paper, about whose opinions really matter and who say," Hey, you're stepping out of your integrity here. You're not living in your vision here. That didn't seem like you." Those are the voices that can have space.

Scott Dorsey: Oh, absolutely, Lindsay, and I think this really applies to how you build your leadership team and how you run with your leadership team also. Once again, everyone's leadership style is different. I am not the type of leader that's going to have a brilliant idea over the weekend and come in on Monday and say," Hey team, here's what we're doing." There are leaders that are highly effective at doing that. I'm more effective listening to others, listening to everyone's ideas, and maybe bubbling up the two or three that I think have the most merit and then being really collaborative on the front end to get everyone's voice and thoughts into a big decision we might be making, and then I anchor it on the decision and away we go. With that kind of collaborative approach, it takes longer, but the benefit is you bring people along in the journey and they feel a part of the decision. I've always found if you're your team feels — they may not agree with every decision, probably don't — but if they feel a part of every big decision and they had a voice and we had a chance to discuss and debate, that the commitment and the speed in which we're able to execute really increases.

Lindsay Tjepkema: Yeah. Well, that sounds like that's true to you and I'm sure there were elements of that that were there when you were in leadership roles in high school and junior high, all the way to now. I'm curious, I mean, you've gone from first- time founder — what if I just signed away my job — to board of directors on some incredible companies and to being that person that people seek out for advice and are asking to be on their board of directors and personal board of directors. We could go down the path of what's that like, but truly, I want to know what that's like for you. What things have remained the same about you from that, sitting first- time in the founder and CEO, like," Do I deserve the CEO title?" mentality, to now being that person that people are seeking out for advice? What do you think has remained the same, like those vulnerabilities that you still carry with you, and what things do you think have been the most marked changes?

Scott Dorsey: Yeah, that's a great question, Lindsay. I hope that most has kind of stayed the same. Probably, in large part, to my amazing wife, Erin, who keeps me really, really grounded, and my daughters, but hopefully most of it has just remained the same, just being the same person, but just having a set of experiences along the way that you're grateful for and you're eager to try to help others, knowing that I had an infinite number of people that helped me every step of the way. When you have a neat experience in life and you have so many people that helped you achieve whatever goal you set, it's really natural to want to turn around and help so many others as well. I think one thing that's different is when you're CEO of the organization, you're making decisions and you're in control. You may not always feel like you're in control, but you're in control of who you hire, who you work with, what strategic decisions you make, and a lot of accountability and pressure comes along with that, but you're definitely in control. Now shifting into the mode of coach and board member and advisor, you're really not in control. You're trying to offer guidance, you're maybe trying to use your power of persuasion to convince somebody to move in a certain direction, but you're ultimately not the decision maker and you also have to get comfortable with that. So I'd say that's probably been maybe the biggest shift for me from life at ExactTarget to life at High Alpha, where I'm coaching, mentoring, advising lots of different entrepreneurs and companies, is just acknowledgement that the person you're advising, the CEO, they're really the decision maker. They need to be comfortable with whatever decision they make and I have to be willing to give my point of view, but also let go, be comfortable letting go, and knowing that it's most important that the leader make their own decisions. Some will work out great and others won't, but that's all part of the learning process that we go through as humans. It's a little bit like with your children, not that it's a perfect analogy, but with your children, as a parent, you do the best you can to share your experience and coach and guide them, but in some areas, they're going to make their own mistakes. And we probably all learned by making mistakes more than we do successes.

Lindsay Tjepkema: Yeah, somebody said once, recently, to me, that success is a horrible teacher. I mean, if you go through a business, if you go through life, and all you have is successes, when things get tough, you literally have no frame of reference. So that's actually a really good transition, is the difference... ExactTarget, High Alpha, both are incredible success stories. I'm very thankful that you started High Alpha. But, I'm guessing, you kind of were back to that first- time founder feel, maybe, because this wasn't starting another SaaS company, this was becoming a VC and investor, and running a studio. A lot of innovation with the way the studio model works, but again, for you, similarities, what did you bring with you versus like," Whoa. Okay, this is different." Like specifically in your role, as a leader of the High Alpha company, what are the similarities and differences there?

Scott Dorsey: It's a great question, Lindsay. The last six years of building High Alpha's been an absolute joy and delight. I've loved every moment of it. There's an interesting mix of similarities, but quite a few differences as well. It's really interesting, with ExactTarget, that was literally my first startup. So I was one for one and got really lucky. We obviously caught this incredible wave of digital marketing and incredible wave of SaaS and cloud, and just a lot of things have to fall your way to have breakout success within the world of tech. So going to High Alpha, it was like going right back down to day one. It was all the risk and uncertainty and fear of doing something new and in doing something different, and being vulnerable to know you may not be successful, but I was excited to do it. I like building, I like learning, I like tackling big challenges, and building a startup studio that starts many companies in parallel. As you know, one startup is incredibly difficult and challenging, and starting and supporting multiple at the same time, really, really, really high bar. But I was really drawn to it because it felt like a very natural way for me to leverage what I've learned along the way, mistakes and successes, leverage the network that we'd built, and hopefully do something extraordinary for Indianapolis and for future entrepreneurs. I sincerely had so many remarkable mentors during my ExactTarget journey and often they would ask me," What do you want to do next if ExactTarget's successful?" And I would always say," I want to be you. I want to be in a position where I can help others and I can support entrepreneurs and leaders the way you've supported me." So shifting into High Alpha, what's been really fun and exciting, as you know, Lindsay, is the concept of the venture studio is brand new. Six years ago, pairing a startup studio with the venture fund, all under one entity was very unique and novel. Doing it around B2B SaaS, we believe we were among the first, if not the first, in the world to start a venture studio focused on B2B SaaS. So that's fun and exciting. So we're one part startup studio, one part venture fund, I knew very little about running a venture firm, and I'm still learning six years in. So for me, being back in learning mode, back on the very early part of that next learning curve has been great, where yes, I'm coaching and helping entrepreneurs, but I'm learning what it's like to run a startup studio along with my partners and same with the venture fund. I'm making sure that I have mentors in my life that I'm calling on and learning from, and six years in, we've learned a bunch, but we still have a lot more to go and we want to be best in the world at what we do. To me, that's what's really, really fun and motivating. I would say the other piece that I would just touch on real quickly, Lindsay, is I get asked often," Do you miss operating? Do you miss being in an operating role?" I usually answer that, we still have 40 employees at High Alpha. It's not 2000, but we're operating. We have core values and culture and we're hiring and we're always trying to get better and refine our models. So for me, it's kind of best of all worlds. I like having a team and having a culture and operating a company, but then also being in this role where we're helping so many others, is a perfect fit.

Lindsay Tjepkema: Yeah. That's really cool. Being a part of that, it's interesting to see behind the scenes and how High Alpha works, and especially as you're raising capital, understanding how a venture fund works and what it's like and what the team is like and how that experience goes. In your role, you are constantly looking for, obviously, businesses to invest in, and specifically, for the studio, looking for founders. So that's how we met. You have, what I can only imagine, is a really exciting challenge, also difficult and very risky responsibility, of finding people that, like me... I was a marketing leader. I was marketing, and that's how you and I met, was talking about B2B podcasting and what could this be like? What do you look for? How do you identify and how has that changed? What's it like to spot people that have never done this before and say," I think you should leave this and do this." What's that like for you? What are the fun parts or the challenging parts, what do you look for? What's that like?

Scott Dorsey: That's a great question. It's probably, maybe, the funnest aspect of what we do, but also you're right, the hardest and most challenging. I think it's more art than science. We're always working a pipeline of big ideas and big markets and new problems to solve, and then a talent pipeline of founders we think that have the skills and the competitiveness and the desire to go build that company with us. So I'd say some of the learnings we've had over the years, Lindsay, that have kind of shaped what we look for, I think the first is, founder idea fit. You're a tremendous example of this. You and I met during sprint week when we were ideating in this idea of a platform for marketers all built around podcasts, and you were living it as a marketing leader, both hosting a podcast, but also thinking about how does that podcast permeate through really large enterprise. So I think first is finding that founder idea fit. It's got to be tremendous. The founder, as you know, you have to be so committed to solving a problem or capitalizing an opportunity or making the world a better place through this business, that you're committed doing it for five, 10 years, maybe longer. So I think that is number one. I think number two, we're looking for just natural leaders that can build remarkable teams. That others want to work side- by- side with and rally behind their vision. I think that's really, really important. Then maybe third is just the grit and determination and competitiveness to just be so convinced of where you're heading, that nothing's going to get you down, nothing's going to slow you down. And as you know, there are a lot of ups, but also a lot of downs in the startup world, and it can be very humbling. There's a lot of rejection that comes when a prospect says no, or a customer says," I'm not going to renew," or investor says," No thanks. I don't think this is a big market opportunity." You have to be a good enough listener that you bring that feedback in, you use it as fuel and motivation, maybe you change course a little bit, but you don't lose your resolve and determination that you're going to be successful. So those are probably the top three that come to mind for me.

Lindsay Tjepkema: It's like almost an insane person. It's like," I don't care how many people tell me no, how many people tell me crazy, how many people tell me this isn't going to be a thing, I'm just going to continue to believe this story that I'm telling myself." Which sounds crazy, but it's what's required. There is no one that can shake me from believing what Casted is and what it's going to be, and that's what's required.

Scott Dorsey: You're so right. If you don't believe it right down to the core, nobody else is, and so much of this role is bringing others along with you: team members, customers, investors. You just have to believe it right down to your bones, right down to the core, that this is going to happen and we're going to shape the future. You have to believe that you can bend the future. One of my favorite quotes is," The best way to predict the future is to create it." It really takes that mindset as a startup entrepreneur.

Lindsay Tjepkema: It is so true because — talking about the best of times and the worst of times — sometimes that's all you have. I mean, going back a year ago for us, we were just about a year into the business and COVID hit. We were in the doldrums of summer — which come to find out is a thing — and things were tough. Myself, and then to my co- founders and the smaller team that we had then, just had to say," We're still going here. We're still on a rocket ship. We've had some turbulence, but we're still going there." Sometimes that's literally all you've got and you got to muster it up.

Scott Dorsey: You're right, you just have to embrace it. It's a part of the journey. With our ExactTarget story, you could listen to it from afar and think," Ooh, that was breezy. That was all easy and up and to the right." But the real story is, there were so many setbacks: difficulty getting funded, product outages that lasted a weekend that put our customers in a compromised position, we had a failed IPO, losing key members of the team that you don't want to lose. There's a lot of heartache along the way, but if you have that determination, you hop right over the speed bumps and you keep going.

Lindsay Tjepkema: Yeah, that's important too, is to share those stories that it's not up and to the right, success stories do this. It's important to remember those too. Speaking of that, with the best of times and worst of times, you have seen a lot of founders succeed, you've seen a lot of founders struggle. So I want to hear common mistakes that you see made, but then we'll maybe wrap it up with advice that you have based on what you've seen work.

Scott Dorsey: Sure, I'd be happy to.

Lindsay Tjepkema: So first, challenges, common challenges and common missteps, that you see among first- time founders and people in this seat.

Scott Dorsey: Okay. I think maybe common missteps, Lindsay, would be getting overwhelmed with the 101 things you need to be doing and maybe not prioritize it properly. So I think time management and fierce prioritization is difficult to learn, but as a startup or scale up entrepreneur, you have to be really, really good at it. So I find the best entrepreneurs are laser focused and they're incredible at prioritization. I think that's really important. I think maybe second would be making sure you're always up- leveling your team. You're not afraid to stretch for hires that are remarkable and might have quite a bit more experience than you do. You just have to have confidence that you're able to recruit anybody anywhere, and what you're building is so special that remarkable people want to be a part of it. When you do that, you can empower them in ways you never even imagined, and it allows you to become your best. I would often answer the question of," How did you grow and develop as a leader from scrappy startup founder to running a public company?" And I would generally answer it as mentors, advisors, a board of directors, and that was certainly, early, very, very important, but I'd say in the later stage it was the leadership team I was able to assemble. They were so gifted, so remarkable, knew so much more than I did about their area of business, or maybe just even scaling software companies, that them being so good, elevated me and just forced me to be a better leader. I probably learned more from them than they learn from me. So that'd probably be the second one, is being comfortable hiring people that are more experienced than you and knowing that's the only way you're going to really scale as a leader. The third, I would just maybe say, is being... And you're so authentic, Lindsay, and I think so good at this, but it's just making sure that you stay authentic and stay true to yourself and you lead the way you want to lead. You lead in a way that isn't what you think other people want you to be doing, but it's just you know, like in your heart," This is the way I want to build a team, the way I want to lead, what I'm really good at," and you find a way to leverage your strengths rather than try to fit into a leadership mould that you think others want you to fit into. That's really, really important.

Lindsay Tjepkema: Yeah. Conviction and discernment are important. Very important. Well, is there anything else that we didn't touch on that you feel like people in this role or are interested in this role or excited about the idea of entrepreneurship or think that it's really glamorous, should know?

Scott Dorsey: I think maybe the last thing I would touch on, and I know you're a big advocate of this also, Lindsay, is having a coach. Coaches really didn't exist in the form they exist today when I was running ExactTarget, so I think my board and investors were kind of my coach. But I think it's really healthy to have a coach who is not a board member, not an investor, they just really care about you and your best interests, and you can have a level of maybe disclosure and vulnerability with them that you may not always be comfortable with, with an investor or a board member. I like to think, as I'm sitting on boards and investing, that I can build a really true and authentic relationship and CEOs are going to be really, really open with me, and I hope that's the case, but you also know in your heart of hearts, as a leader, sometimes you don't want to show your vulnerability or you don't want to expose what you don't know or a mistake you've made. I think having a disconnected coach or a mentor can be really, really useful. Put it this way: of all the CEOs I work with, I've never had one regret getting a coach. I only hear really rave reviews and accolades about getting that support and also maybe getting that support for your leadership team as well, because you want to help them grow and you want to grow together as a team. So I think that notion of a coach can be quite powerful.

Lindsay Tjepkema: Yeah, absolutely. I agree with everything you said, and it's also lonely. It's ironic that you're surrounded by so many voices and so many advisors and so many people that want to help and also those that you're leading, but truly it can be lonely because you're not surrounded by people that you can be fully transparent, fully vulnerable, fully whatever it is, with. So it is really, really important to have that community and at least that one person that you can go to.

Scott Dorsey: Maybe last thing too, Lindsay, is make sure you have fun. Leadership and building companies is, yes it's hard work, but it's also really, really fun. Don't forget that more things are in your control than you think. Sometimes you lose sight of the fact that you do have a lot of control. One of the benefits of being a CEO is you get to make hiring decisions, you literally get to decide who you work with. You literally get to decide who you work with every day. You also get to decide direction of the business and many other decisions along the way, and while you have constituents that you need to listen to and get their feedback, you're, ultimately, in control and you can build whatever type of organization you want to build. I've had a number of entrepreneurs approach me and say," I'm not sure I want to build the company any bigger than 50 people." I'll say," Why not?" And they'll say," Well, it just gets too bureaucratic and too much structure." And I'm like," You're in charge. Build the company any anyway you want. If you want to build a new model for how to build and scale a company, do it." You don't have to be beholden to some old antiquated notions of how companies should be built. You're in charge. So remember: you're in charge, you have control, and also, make sure you have a lot of fun along the way.

Lindsay Tjepkema: I love it. It's a wonderful place to leave it, on a nice high note. Very inspiring. Thank you so much. Thank you for everything, for your partnership with me and with the business, and of course, for sharing your insights here today. This was lovely.

Scott Dorsey: My pleasure. Thank you, Lindsay. I enjoyed it.

Lindsay Tjepkema: There you have it. There we were, Casting a Vision. I can't wait to hear how it resonated with you. So let me know, reach out on LinkedIn or find me on Twitter @ CastedLindsay or Casted @ GoCasted. Thanks, and be sure to join us next time for the next episode of Casting a Vision.


Today's conversation is with Scott Dorsey, Managing Partner of High Alpha. High Alpha is a venture studio that launches, scales, and invests in enterprise cloud companies, Casted being one of those. Not only is Scott a Casted board member, but he is also a partner and mentor to our host Lindsay Tjepkema and CEO at Casted. Today, he shares what it was like being in Lindsay's shoes when he started ExactTarget and what it's like coaching other industry leaders as he continuously grows as a leader himself.

Today's Host

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Lindsay Tjepkema

|CEO, Co-founder

Today's Guests

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Scott Dorsey

|Managing Partner, High Alpha