🎙️ Scaling Companies & Leveraging Community in Indianapolis w/ Scott Dorsey, Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha
Listen on: Spotify, Apple Podcasts, Amazon Music
On this inaugural episode of Outsider Inc., host Ian Hathaway talks with Scott Dorsey, co-founder and former CEO of ExactTarget. Scott shares his journey from founding ExactTarget in 2000, through its $2.5 billion acquisition by Salesforce in 2013, to his current efforts in fostering entrepreneurship in Indianapolis via HighAlpha. Their discussion covers launching a company when the dot com bubble burst, early sales and fundraising strategies, and ExactTarget's transformative impact on Indianapolis' tech ecosystem. Scott emphasizes his philosophy of building a company and a community, revealing how leveraging local talent and fostering a strong company culture contributed to ExactTarget's success. He also discusses the importance of supportive ecosystems for tech startups and his continued mission to invest in and support local entrepreneurs.
Show Notes:
(03:15) Scott Dorsey's Early Career and ExactTarget's Founding
(05:30) Challenges and Early Successes of ExactTarget
(11:44) Raising Capital and Building a Sales Team
(18:35) Transitioning to Enterprise and Securing Venture Capital
(24:03) Navigating IPOs and Acquisition by Salesforce
(30:23) Founding High Alpha: A New Venture Studio
(32:19) High Alpha's Unique Approach and Methodology
(36:06) Building a Tech Ecosystem in Indianapolis
(41:49) The Orange Culture and Its Lasting Impact
(47:16) Personal Insights and Leadership Philosophy
(51:12) Beyond the Bio w/Scott Dorsey
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Scott Dorsey - Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
AI-Generated Transcript
Scott Dorsey: [00:00:00] I'm hopeful to be investing in and supporting entrepreneurs that, yes, want to build breakout companies that transform an industry, but also see the benefits of doing it in a way where you can really make a difference in your hometown, in your community. And we were blessed with an opportunity, I think, to really change the tech landscape here in Indianapolis.
Ian Hathaway: Welcome to Outsider, Inc. I'm your host Ian Hathaway. Today's guest is Scott Dorsey, a pioneering tech entrepreneur, investor, and community leader who's played a central role in transforming Indianapolis into a thriving tech hub. I've been following Scott's journey for years and I'm excited to share his incredible story with our listeners.
Scott is best known as the co founder and CEO of Xactarget, a marketing automation platform that he led from its founding in 2000 to a 2. 5 billion acquisition by Salesforce in 2013. Under Scott's leadership, Xactarget became one of the Midwest's most iconic [00:01:00] tech success stories, proving that world class software companies can come from anywhere.
Following the acquisition, Scott stayed on to lead Salesforce Marketing Cloud, working directly with Salesforce founder and CEO, Mark Benioff, and integrating ExactTarget's innovative culture into one of the largest tech companies in the world. Today, downtown Indianapolis boasts a Salesforce tower, home to more than 2, 000 employees, and serves as a symbol of the city's success.
But Scott didn't stop there. After Salesforce, he turned his focus to nurturing the next generation of entrepreneurs, launching HiAlpha in 2015, a venture studio and fund that has incubated and invested in dozens of enterprise software companies. He also founded NextTech, a non profit dedicated to bringing computer science education to underserved communities, and has helped shape Indy's tech and sports ecosystems through his leadership and philanthropy.
Scott not only built a legendary tech career, He started a movement, building a community while building a company, helping to transform a region [00:02:00] and inspire a new generation of entrepreneurs to build close to home. I'm excited to talk to Scott about his journey from founding and scaling ExactTarget, to launching HiAlpha, to the unique advantages of growing companies in the Midwest and how he's helping foster a vibrant startup community in Indianapolis. Scott Dorsey, welcome to Outsider Inc.
Scott Dorsey: Thank you, Ian. I really appreciate the warm welcome and the kind words, and I'm beyond honored to be the first guest on Outsider Inc.
Ian Hathaway: Scott, I'm super excited to have you joining me today for this inaugural episode of Outsider Inc.
And as we've discussed many times before, I think your story is this prototypical example of how a nascent startup ecosystem Can evolve into a thriving one. You led this sort of unlikely team in an unlikely place to a massive success, drawing in people and resources from around your region in a way that has really left a lasting impact.
But then. Rather than riding off into the [00:03:00] sunset, you doubled down on the next generation with this large ambition of making Indianapolis a destination for great software founders. I think it's truly a remarkable story. And so I'm just super pleased to have you with me today to launch this platform.
With that said, if we could go back to the beginning of ExactTarget, which is a company you co founded in late 2000 with Chris Baggett and Peter McCormick. Taking principles from database marketing and applying them to the fast growing online world. Tell us a little bit about where this initial idea came from and how you knew it was an idea worth pursuing.
Scott Dorsey: Sure. Thanks, Ian. So, I think every founding story, you know, has an interesting backstory. And, uh, in ours, I think it was quite unique. I was just finishing up graduate school. I went back to get my MBA at Kellogg at Northwestern there in Chicago. And, uh, it was a beautiful time to be in school when the Internet was just coming of age.
So I really leaned into entrepreneurship, Internet [00:04:00] business models, even tech ecosystems. In fact, our capstone course was a trip to Silicon Valley to bring back recommendations to the city of Chicago on how we could drive more. Tech innovation and entrepreneurship. So I, I look back on that time and really kind of realized I was a prepared mind.
I was studying internet business models and thinking deeply about software and entrepreneurship, my co founder and brother in law, Chris Baggett, an extraordinary evangelist thought leader. Serial entrepreneur. He really had the database marketing background, kind of growing his career with our Donnelly and helping large brands leverage all the data that they had on their customers to be more relevant and more targeted in their communications, which back in the day that was largely print.
And so Chris really had the vision of how the database marketing world would be activated in the online world. He also owned a small business in Indianapolis, started experimenting with email marketing and quickly ran into a lot of [00:05:00] dead ends for a non technical marketer or business owner who didn't know SQL, didn't know how to write HTML, and it was really a blending of our experiences along with our third co founder, Peter McCormick, that put pen to paper on a business plan and gave us the courage to get started with ExactTarget.
Ian Hathaway: That small business of Chris's was, in fact, a local dry cleaning chain, which is, of course, not the most common of launch pads for a multi billion dollar tech business. Speaking of doing things in an unconventional way, you launched this company in Indy several months after the dot com bubble burst.
Feels pretty bold in hindsight. What ultimately worked out probably wasn't so easy to see from the beginning. Indy's tech ecosystem wasn't well developed at the time. You were three first time founders with no real experience in tech. The market had just imploded. What made you think that this was a great time [00:06:00] and place in the team and that you were ultimately going to be successful?
Scott Dorsey: That's a great question, Ian. What were you thinking, Scott? I'm not sure if it was bold or naive or maybe, you know, maybe a little bit of both. And ironically, I had my two, two young daughters and, and, you know, shortly thereafter, a third on the way and a remarkably supportive wife. My wife, Erin, was excited to get to Indianapolis, which is her hometown, to be surrounded by her sisters and parents and nieces and nephews.
So we had a, we had a strong personal pull to Indianapolis. But, uh, it really felt like the moment was right. I think of the time we're in now where there's just such a world of infinite possibilities that AI, gendered AI is bringing to us. I felt the same way about the internet, and I know Chris did in a big way as well.
So we felt like our timing was in, in many ways really, really good that marketers were just in the early days of figuring out how to leverage the internet and how to leverage digital communications like email. I think we were naive in Not really knowing what we're doing, but just knowing that we wanted to build a business and that we [00:07:00] build a product and kind of sell one customer at a time and try to build this thing from the ground up very much in a bootstrap fashion, but the broader macro created some real challenges.
And then 9 11, you know, happened shortly after we founded the company. So we built some resilience, you know, early, uh, into, into the company and into our founder mindset that, you know, carried us for a long, long time. And I think ended up being a silver lining sometimes when it's a. Difficult environments to start companies.
It's actually a positive because you have less competition. And if you can figure things out and, and build a sustainable business, when the environment is perhaps more fertile or healthier, more prosperous, you're very well positioned.
Ian Hathaway: I know there's this balance between you want to be early. On a macro trend, but not too early.
Did it feel at the time, like you were on the cusp of something? Did you have that sort of insight at the time that it felt like the, the perfect time to launch this company?
Scott Dorsey: I think so. We enter, we certainly, you know, [00:08:00] some of the attributes at that time, there were. Existing competitors, you know, there were incumbents.
They were largely focused on larger companies, you know, kind of more B2C orgs up in the enterprise segment. So there was less competition down in the small business segment, but there was enough, I'd say mindshare and understanding that was developing around email and digital marketing. That we're able to kind of tuck in and capitalize on that.
But early days, it was a lot of evangelism. It was a lot of why email, why digital marketing, having to overcome fears and doubts about email as a viable channel, having to really be an early pioneer and what permission meant. Seth Godin had just written an incredible book, Permission Based Marketing. So we really leveraged his principles and his writing just to teach marketers and small business owners about what true permission meant and how valuable it could be as you're building that deep customer relationship over the, over the arc of time, we started moving up into the mid market.
We started selling to enterprises. And then we [00:09:00] started getting RFPs and that was a happy day. You know, RFPs can be a little challenging because you're going up against a broader competitive set, but that's when you know, the market's pulling you rather than you're just pushing. And we started to see that happen.
We were, we knew we were onto something pretty big.
Ian Hathaway: I want to get to that evolution in a minute because I actually think that's a really important part of your journey and a lesson for founders out there today who make that evolution from small and mid market companies to going into enterprise. But if we could go back to the beginning, uh, you used the word evangelism, so would love to know how you were able to get those early adopters, those early customers, and convince them to work with you.
Scott Dorsey: A couple different ways I would say our, our founding team, the three of us really balanced each other out nicely. We were all very focused on marketing and selling, but Chris really was kind of the evangelist thought leader who spoke at events, did a lot of writing and blogging in the later [00:10:00] years, you know, and really cast a big vision for the company.
And then Ian, we were just hustlers, you know, all three of us, you know, the old adage of, you kind of need a hacker and a hustler. We were really three hustlers, and fortunately we found some very talented people on the engineering and product side over the course of time. But early on we were selling, marketing, evangelizing, and those early customers were really friendlies.
You know, we really leaned heavily on colleagues, peers, friends we had worked with. In a variety of different industries to be our early adopters and give us a chance. And, uh, those were many of the early customers. We also traveled to events, believe it or not. We went to the clean Oh, one show to leverage Chris's expertise in dry cleaning.
We started realizing early in. That small businesses were difficult to sell to one at a time. But if we could sell a franchise system, we could bring dozens or hundreds of small businesses onto our platform. So we went to the International Franchise Association show and met in Indianapolis based franchisor called Wild [00:11:00] Birds Unlimited.
And they became one of our early development partners on building kind of a two tier platform that was really oriented toward franchisors and franchisees. There's a lot of ingenuity, a lot of creativity. We worked with agencies to be their tech platform of choice, and then they would bring us into their accounts.
So in many ways, we started working with larger brands when we were still pretty small, scrappy company, but we were leveraging the credibility. Of agency partners. So it was a lot of creative thinking, I would say. And, uh, you know, necessity is the mother of invention. We found lots of ways to go to market in creative and affordable ways, since we really didn't have much capital.
And we were kind of first timers figuring out along the way.
Ian Hathaway: Let's talk about capital. Obviously, the funding environment has evolved substantially in the two plus decades since you launched exact target. I've heard you describe this 200, 000 friends and family round, which was the first capital you [00:12:00] raised and were very intentional about it.
Right. It was truly a friends and family, many friends and many family, not this, you know, one rich uncle who wrote this 200 K check talked to us a little bit about what it was like the thinking going into putting that round together and ultimately getting an army of smaller checks.
Scott Dorsey: Happy to you know the three of us shipped a little bit of money and we got started committed that we work without a salary for as long as we could we could make that work and then we did meet with a few vcs early on in and your point we were three first time software entrepreneurs trying to.
Raise money during a very difficult time and doing so in Indianapolis. So if we, we had little success, so it was almost more out of necessity that we raised their friends and family around. So we did, we raised 200, 000. We were really terrified that we would lose everyone's money. So we really asked everyone to write.
Whatever check they were comfortable losing, they wouldn't miss it and it [00:13:00] wouldn't harm our, our family relationships. We wouldn't have any extra strain around the dinner table over Thanksgiving weekend. So we really did. We scooped up a lot of five and 10, 000 checks to get the 200, 000 together to give us enough capital that we can kind of get up and running.
Ian Hathaway: You've raised a couple hundred K, you're up and running. You eventually meet a man named Bob Compton. I know he eventually helped get an angel round together, but how did you meet him? Who was he? What role did he play?
Scott Dorsey: Yeah, Bob, Bob's a remarkable person, Ian, and he was a big change agent for us. We, we were kind of working our way through the 200, 000.
We were not paying ourselves a salary. We really needed an appropriate round of angel capital. And, you know, had many, many meetings and just nobody, a lot of interest, but nobody who would really commit. And Bob, Was really our first commitment from an angel investor. And Bob had incredible background, both as a leader, tech leader, venture investor, and, uh, an angel investor.
And he, [00:14:00] he kind of fell in love with what we're building. We had a warm intro to Bob, so he was willing to. Take a breakfast meeting with us. And he got excited about what we're doing. And he, he committed 100, 000 investment. And then two, three weeks in, he got so excited working with us that he increased it to 500, 000 and became our chairman.
And he had so much credibility in the local market that when he said he was in. All of a sudden, many, many other individual investors came in and we, we had kind of that stamp of credibility or approval that we really were lacking. So Bob was an incredible coach and mentor to us over the years, but he really gave us kind of the first big break on raising capital and giving us a chance to really start scaling the company.
Ian Hathaway: Kind of looking back on things and knowing what you know now about, you know, building ecosystems, how important is it for a city to have a Bob Compton
Scott Dorsey: essential, you know, just so important. And that would often ask us if if you're successful with the exact target, what would you want to do next? And I would always say I [00:15:00] want to be you.
I want to find a way to accomplish that. Support young entrepreneurs and put capital into the companies and provide coaching and support and really give them a chance to build something special. So Bob was an incredible role model and a real difference maker for us. And I think whenever you look at tech ecosystems that are really thriving.
They have a lot of Bob Comptons. I was just in Utah last week, and I love Utah and the people and the tech community, and they have so many successful tech entrepreneurs who've had an exit, and then they just pour it right back into the community. Active angel investing, coaching, mentoring, and that creates a flywheel that lifts these tech ecosystems in a really profound way.
Ian Hathaway: I'm sure we're going to get to your role in doing that in Indie here shortly, it's a big part of your story, but I guess going back to kind of the early days, you know, you've raised some early capital, you've gone to market, you were remarkably successful early on, I don't know if the terminology of [00:16:00] You know, product market fit was rolling around in your head at the time, but it seems like you found it early on, you know, you did 300 K in revenue in year one, 3 million in year two, 9 million in year three, it doesn't typically happen that way, as you know, by now, were you aware that you had.
Caught lightning in a bottle at the time. What did that feel like? And why were you so successful so early on?
Scott Dorsey: We had a selling mindset. You know, I now look back on that, that growth with even more awe and surprise than when I was kind of living it because we've started so many companies at high alpha and very few have had that kind of an early trajectory on such a small amount of capital.
I think we had excellent product market fit. We had very, very good market timing and we had a. Big selling mindset. You know, our, the three co founders all had selling backgrounds. We brought some incredible sellers into the organization early. One of Bob's areas of advice was never hire one AE at a time, always hire them in classes of three so you can train them, [00:17:00] enable them, they can support one another, create some friendly competition, and they can kind of be a cohort that hopefully grows with the company over time.
And so we, we hired in threes. Another Really wild thing we did, Ian, after the internet bubble had burst, is we had a lot of friends who were looking for that next job, but there wasn't a lot of hiring happening in e commerce and tech. So we hired them early as independent sales agents to sell ExactTarget into the market.
Uh, we gave them equity, we paid commission on anything they sold, and we kind of had a promise that if we turned into a real company, we'll hire you. So we actually had a Heavily oversized sales organization that when the angel round of financing came in and we started to get traction from a sales perspective, we hired everybody and we were way over tilted the sales, but it really paid big dividends for us.
So I think even when we were 50 or 60 employees, we had a 20 person sales team, which you, you often wouldn't see [00:18:00] in today's environment. Almost unknowingly, we built a tremendous amount of sales capacity from really talented sellers who were deeply committed to the company. And, uh, and also we're competitive with one another in the friendliest way.
And, uh, we also were determined to set aggressive quarterly sales goals. And never, never miss them. We held ourselves to a very high standard and have had a lot of intensity, I think, around going out and finding customers and finding new markets.
Ian Hathaway: Yeah. Never let a good crisis go to waste. Right. Take advantage of that market opportunity.
Scott Dorsey: We were very opportunistic.
Ian Hathaway: Well, speaking of that and turning points for the business, one that, you know, you hinted at earlier was this evolution of serving small business, local business, mom and pop kind of shops to mid market, and then ultimately this evolution to enterprise, which is a very different go to market motion, very different sort of process and thought around product development.
Where did that initial [00:19:00] insight come from? And How were you prepared to make that evolution might be some things that founders that are going through that journey today, where they maybe haven't evolved to the enterprise, but they can think maybe two steps ahead about what going through that transformation is like.
Scott Dorsey: It's a very good fortune we had is that we configured and built our products in a way where every feature had an on off switch. So we left ourselves kind of infinite flexibility and how we bundled and packaged our product. So traditional SaaS pricing, kind of good, better, best. We, we really adopted that very early and really built our platform in a way where we could add very sophisticated capabilities that were well suited to the enterprise, but we didn't have to overburden our small businesses with too much complexity.
And that became a really important design principle that I think really kept us honest over the years is that we wanted the product to be simple. Elegant, easy to [00:20:00] use for the small business or the non technical marketer, but very sophisticated for the more technical user and the larger enterprise. So the journey from small business to enterprise was one of just being opportunistic.
We would ensure way up and we'd close the deal and then maybe stretch to make them happy and satisfied and fill in any functionality gaps we had. And then once we. We're successful. We're like, Oh, okay. We're actually very good at serving e commerce or we're very good at serving the financial market or, Hey, this daily deal segment is one that, uh, has, uh, an amazing amount of potential.
So we would kind of stretch our way into. Serving a very demanding customer, maybe in a new market. And then once we built that confidence, then we'd really target that vertical in a big way. So Expedia was a breakthrough win for us in the travel space. And then over the course of time, we landed Travelocity and kind of many others, bank of America was a breakthrough win in banking and finance.
And then, [00:21:00] you know, we were able to land Fidelity and Charles Schwab and, and Groupon was a big win we had in the daily deal segment. And then we found lots of others all around the world. So I think we were, we were very good at having. Uh, willingness to stretch and then, uh, being agile enough that when we, we saw kind of a hot area of the market, we were having success.
We pour a lot more resources into it.
Ian Hathaway: Speaking of resources, you have this early product market fit, impressive growth. You're landing these iconic companies as customers. You eventually in 2004 raised the series, a venture capital round with an iconic firm insight partners. Based in New York. How did you get connected in with them?
And was there any resistance from them about you being an Indie versus being in San Francisco or in New York?
Scott Dorsey: They were so supportive in, you know, 2004 were three years along our journey. Our only funding has been friends and family and angel. We've been [00:22:00] Super, super capital efficient and really up to that point, didn't have any luck raising venture capital.
So we really had the mindset that we probably would never raise capital from venture capitalist. And then insight reached out to us, Kobe Fuller, who's become a dear friend and is a partner in upfront ventures. He was a junior guy right out of Harvard working for insight and, uh, and really convinced me that insight had a lot to offer and in particular had a lot to offer around.
Helping us learn, helping us grow, helping us scale, learning from their team, but also learning from the 50 or 60 other portfolio companies that were at a similar stage. And, uh, we just really kind of fell in love with the idea of accelerating our learning and having a broader sample of portfolio companies that we could learn from.
And then also interestingly enough, a part of their offer was. A secondary offer to allow founders and early employees and some early investors to take a little bit of money off the table just to lock in a little [00:23:00] financial security and and put themselves in a position where we can kind of dream bigger and get more aggressive about how we thought about growing the business so it's been kind of interesting as i looked at tech companies over the arc of time sometimes you know enabling founders or team members or investors to do you risk their investment and take a little money off the table really opens up the aperture.
On getting more aggressive and ambitious, so that insight round accomplished a lot for us, and they turned out to be just remarkable partners. I was scared. I was intimidated. I was excited. You know, I, I signed the term sheet, you know, on, uh, in Manhattan and thinking, you know. We're, we're a little Midwest company out of Indiana.
And am I going to be able to scale as a CEO or will they want to replace me? So, you know, you, you bring a lot of fear and doubt and concern into those decisions, but insight turned out to be just an extraordinary partner. Never pressured us to move from Indiana. They really saw the benefits of building a company in a market like Indy and in the Midwest, and we just made sure we were [00:24:00] committed to leveraging those advantages that were kind of inherent in our geography.
Ian Hathaway: Another pivotal moment, of course, you eventually take the company public in 2012, defining moment. There was actually a failed IPO before that, which in 2007.
Scott Dorsey: Oh, you have to bring that up. Cute.
Ian Hathaway: Yeah. But you've also talked about that as being a blessing in disguise, because by the time you actually took the company public, you were in a much better position to be a public company.
Talk to me about, you know, that whole journey navigating the financial crisis and ultimately getting ready to take the company on the public exchange.
Scott Dorsey: It was 2007 from the friends and family angel and then the primary that came in from insight. We had only raised six and a half million in primary capital and we still had almost that much on the balance sheet.
We found a way to grow the business in a really extraordinary capital efficient way. We were finishing 2007 at 48 million in gap revenue, and that was a time when small SaaS [00:25:00] companies were going public and getting very well received and successful offerings. And I would say we never had like a early dream or goal.
To be a public company, but we really felt like it was a smart way to raise capital and, and kind of raise our stature as an enterprise software company. And it was at that moment, we're starting to kind of expand into some of the larger enterprises. So we filed the go public December of 07 and in a very Midwestern collaborative way, we had an all hands company meeting.
We're in a local theater. And we pressed the button together to file our offering with the SEC. So it was a big moment of celebration and a shared moment of celebration and, and all the goodness that was going to bring to our company. Well, fast forward one or two months into 2008, boom, all of a sudden the financial crisis hits.
No IPOs are happening and certainly. Little small sass company out of indianapolis exact target we were going to be the first to really break through the market so you know really the advice we had from [00:26:00] our board in the investment bankers were to stay on file. And just kind of wait until the IPO market started open up again so we stayed on file i'd like to describe that timing as we had like all the burden and responsibility of a public company with none of the benefits didn't have the capital didn't have the halo or the successful feeling of going public but still had a printer quarterly numbers.
You know, had to update our filing, had to update analysts, you know, it turned out to be a lot of work and, and also a little scary that you're sharing all of your financial performance and competitive positioning with your, with your broader competitive set. So we started to get to the end of 08, early 09, and it just was evident it wasn't going to happen.
And I was, I was very reluctant to. Pull our filing. I felt like it would be a sign of failure. It'd be disappointing to our team, but it really became inevitable. And at the same time, we started receiving a lot of inbound interest from later stage investors who saw a lot of potential in our company. And I'd say other SAS companies that just weren't able to get public, but we're still pretty amazing companies.
[00:27:00] So we ended up raising a significant round of capital from battery ventures that took a big chance on us. And, uh, we announced that we were pulling the IPO the same day as the funding, created kind of an internal campaign and mantra called better than an IPO, and just picked ourselves up by the bootstraps and got our team focused on what the future held and how we were actually better off executing our vision and our plan as a private company.
And, and we, we tackle the public markets later. And, uh, you know, fortunately that worked out remarkably well and was a, was a silver lining. It was probably one of the best things that ever happened to our company. I think we would have been probably ill prepared had we actually been successful going public the first time.
Ian Hathaway: A year later, you had a number of suitors come knocking. One of them was Salesforce who bought the company for 2. 5 billion, which was a hugely transformative moment for you, your team. The Indy tech scene and really the whole region. What [00:28:00] made sales force feel like the right fit for you? And how did you handle the personal and professional weight of making that decision?
Scott Dorsey: It's a great question. And, you know, going all the way back to the early years of exact target, we thought of ourselves as a data platform for marketers and a digital marketing platform that would allow marketers leverage data. And. We had a mindset that we want to integrate into any data source imaginable for our customers.
And we actually were one of the first Salesforce partners. To drive an integration, even before the app exchange existed. So we integrated into Salesforce CRM. We're able to pull data out of Salesforce and help marketers leverage that data within our platform. So they were an early partner. And we were an early customer.
And we learned so much along the way. In many ways, I always felt that Salesforce was kind of a big brother. And what they were pioneering in the world of sales automation, we were replicating in a smaller way in the world of [00:29:00] marketing. So always had a partnership, always had a tremendous amount of admiration for the team, but we were public.
We were doing great. We were five quarters in. I was actually, believe it or not, enjoying being CEO of a public company. We had met or exceeded plan. Top line and bottom line, five quarters in a row had an amazing base of public investors and, uh, and sales force came knocking. And, you know, of course you, you take that kind of an offer very, very seriously as a, as a public company, you would as a private company, but even, even more so as a public company.
So. We convened the board. We hired JP Morgan who had helped us go public. We hired an amazing set of legal advisors and really made sure we looked at the opportunity and in a really significant way. And Salesforce had done two acquisitions in the marketing tech space. They had acquired buddy media and radiant six, but their customers wanted more.
They wanted a data platform. They wanted a multi channel digital marketing platform. And the gaps that Salesforce was seeing in their offering were very, very nicely [00:30:00] filled. So conversations heated up. It took quite a while to negotiate and figure out if they were the best suitor, but ultimately we kind of brought it all together and had a, had high hopes for what it would mean for our city and also for our team and our customers.
Ian Hathaway: Yeah, it's a remarkable outcome and one that I'm sure you're very proud of and has left an undeniable mark on the city forever. You know, shifting gears, you spent one to two years and. Inside of Salesforce working with Benioff, but you ultimately leave the company and instead of riding off to the sunset, you decide to double down and roll up your sleeves, starting a high alpha, which is a venture studio model based in Indy focused on B2B software.
Was that decision like for you to ultimately dig back in, double down on Indy and to pursue this model specifically?
Scott Dorsey: I was so lucky and, you know, friends and kind of colleagues I'd worked with, Christian Anderson, Mike Fitzgerald, Eric [00:31:00] Tobias, had started to work on this idea of a startup studio and approached me to see if maybe I would invest or, you know, had any interest in being a part of it in some way.
And I kind of fell in love with it. Their early ideas and vision for high alpha. And for me, it was the absolute perfect vehicle to take everything I had learned and the relationships I'd built and the network that had been established and poured into something new at the time. There were very few venture studios in the world.
And we, we really locked in on this idea of one part startup studio, one part venture fund and building the dream platform of services. And support system for future entrepreneurs and really tried to incorporate all of our learnings and mistakes and come up with the dream platform that would give entrepreneurs an outsized chance of winning and building breakout company.
And if I go all the way back to my Kellogg days of studying. Tech ecosystems and really thinking about how to ignite more innovation in the Midwest. [00:32:00] Think about the experience. I had an exact target where I just had an extraordinary amount of support from the city, the state, local CEOs, universities, I just felt so supported.
It makes you want to give back, but also makes you want to do something innovative where you're continuing to learn and continue to kind of break new ground. And Hyalpha was the beautiful way to bring that all together.
Ian Hathaway: Tell me a little bit about your process. So it's a venture studio, you're incubating ideas, you're bringing in resources, and you're also bringing in co founders, leaders to run these companies day to day.
How do you think about The ideas that you're going to pursue, the people you bring in, I mean, you mentioned that it's not lost on me this moment in time of the rise of generative AI. And you've mentioned that that feels like the days of the early internet when you were launching exact target. Just kind of walk me through.
How you think about what's next, what are the priorities and how you ultimately bring all those pieces together to launch a successful company?
Scott Dorsey: You bet, you know, and we we've evolved a great deal over our [00:33:00] nine, almost 10 years, you know, in high alpha. So, you know, think of the first pillars of startup studio.
Second is a venture fund. And our third is a group we call high off innovation. That's CEO, Elliot Parker, that takes our studio blueprint and works with big corporates and universities. To create their own studios and their own spin outs in many, many different fields outside of B2B SaaS could be agriculture, health, life sciences, pharma, but our methodology we developed in the early years centers around a notion, what we call sprint week, where we bring in ideas that have been vetted research.
We have a point of view and then we immerse ourselves in a very time constrained way to go find the market opportunity. And within that week, we are doing a tremendous amount of customer validation. We're coming up with a company name, company brand, doing early high fidelity product design. We're building go to market strategies.
And really we try to reach the end of the week where we have kind of an internal pitch competition [00:34:00] where we're locking in on an idea and a company that we want to go ahead and start. And, and the really cool thing is in some cases, their ideas that we've been nurturing within high alpha, and we. Find founders with a similar vision and many other cases founders bring us ideas or partners bring us ideas.
We've started companies with service now with with many other corporates, but at the end of it, we want to we want to have conviction that it's a really big opportunity and that we have some built in competitive advantage from the beginning that kind of a non high alpha company wouldn't have otherwise.
Ian Hathaway: So speaking of competitive advantage, especially at this stage, you know, the idea, the market, the support is one thing, but really it comes down to talent. You've been on both sides of the table, building early companies, attracting early talent, scaling talent, and now as an investor, what are the things that you look for?
Especially early on in a founder,
Scott Dorsey: such a great question. He ended, I'm still learning, you know, nine, nine and a half, 10 years in, I'm still [00:35:00] learning, you know, for me, I'm a very relationship driven, very culture driven. So, you know, I'm looking for founders and leaders who, who I think are just good humans and they're going to build the company with.
Strong values and high character and they're a leader that others really want to follow and they've got a vision of how to build an organization that amazing people want to be a part of say that's probably part 1 part 2 is they've got some unique insight they've got some knowledge of a problem they want to solve or category that they're entering and it's a collection of their life experiences and work experiences that Put them in a position similar to what we had an exact target, where they have a unique insight into the, into the future and into the new world.
I think that's super important. And the third is probably just a maniacal drive, competitiveness, resilience to put the effort in that it takes to build an early stage company. And a willingness to do it for a long period of time, because, [00:36:00] you know, as you know, it just takes a long time to build these companies and you really got to stick with it and have a lot of grit and determination.
Ian Hathaway: I'd like to, you know, shift gears a little bit. A couple questions about, uh, Indianapolis, the, its evolution, its future, and maybe just more broadly, thoughts on the Midwest. ExactTarget is credited with sparking. The tech boom in Indianapolis, both from the talent it nurtured and wealth it's generated and founders it's inspired.
You're a student of ecosystems, you know, the story of Fairchild Semiconductor, this entrepreneurial spawning. Brad and I talk about it in our book. We call it entrepreneurial recycling. It's not just that the big event happens, but then what happens after that? Almost a decade of, you know, hindsight to look back, what have been some of those ripple effects that have occurred in Indianapolis following the success of exact target?
Scott Dorsey: I think it's really an interesting question, Ian, and you've done such great research and writing on this topic. The years we were [00:37:00] building exact target, we cared deeply. About building a company that really gave back to Indianapolis in a profound way.
And why did we care so deeply about it? I really think it was just the remarkable support we received from everyone in the community. As I mentioned earlier, every mayor, every governor, university presidents, CEOs of larger companies that were willing to become early customers, not even being from Indianapolis.
I was blown away by the warmth, the support, the helpfulness of the community. And when you feel that. You want to do something remarkable for the city. You know, that's fueled me really for the last 20 years. What's interesting today, Ian, is I think that doesn't exist for many entrepreneurs, you know, many entrepreneurs are building companies in a virtual or hybrid manner where their teams are very, very geographically dispersed.
There's certainly benefits to that approach, but I think it's also challenging to do your best work. Solve problems quickly and be a high performance culture and high performance org [00:38:00] when you don't have kind of a center of gravity. So it's really interesting my work at High Alpha and as I think about the future I'm hopeful to be investing in and supporting entrepreneurs that yes want to build breakout companies that transform an industry but also see the benefits of doing it in a way where you can really make a difference in your hometown in your community and we were We were blessed with an opportunity I think to really change the tech landscape here in Indianapolis.
So you go back to the early days. The early challenges, literally first couple of years of starting exact target that the tech community would talk about would be that we had, we had no direct flights, we had a very old airport, and we did not observe daylight savings time. So those were a big problem.
And then we really had no connectivity to other parts of the country. And it was extra difficult, I would say, to attract capital from cities and states, you know, outside of India, outside the Midwest. And then over the course of time as we were building all of a sudden, more local restaurants are being opened and [00:39:00] more downtown housing is being built.
We got a new airport and then you referenced earlier Indy has, uh, is really known for sports and an amazing group of leaders in our city that That built a strategy 40, 50 years ago around being the amateur sports capital of the world. And then all of a sudden we host the Superbowl in 2012 and then new hotels are being built.
And it's been a joy, I would say, to see the growth of exact target in the tech community kind of happened in parallel to the growth of our city. I think we played a small role in it. That's as rewarding as anything, you know, looking, looking back on it many years later.
Ian Hathaway: I might go a step further and say that you played a very active role in that, right?
But I think it's important, this notion of building a community while building a company. You've talked about it a little bit before about your need to cultivate local talent, and that potentially forced you to form stronger alliances with the great local universities in Indiana, which of course then [00:40:00] benefited those universities and those students as well.
Just talk a little bit about that strategy for you, how you knew that building a community while building a firm was not just what you wanted to do as a means of giving back, but it was essential to the success of the company.
Scott Dorsey: Yeah, really, it really was. And I think it's, I think entrepreneurs need to think really strategically about where they're located and how to leverage their unique benefits and how to build some competitive advantage.
So if you're in the Bay Area, you know, you can benefit from immense talent and most of your friends are in tech and probably a little easier to raise capital. You know, in Indiana, those, those were not our inherent benefits or advantages, but incredible universities were a real advantage. So Indiana University, Purdue, Notre Dame, Notre Dame.
Rose Holman, Butler, Ball State, DePauw, you know, we just had this incredible network of universities. And we really felt that if we could bring young talent into ExactTarget, we could help them grow and develop, it'd be a pretty incredible way to scale the [00:41:00] company. So we did everything from create a robust internship program, where we Created a spectacular experience for students.
They go back to campus and talk about what an amazing internship they had with exact target. And all of a sudden we build a brand on campus. And then we became very active hiring undergraduate students and bringing them into the company. And that was just one example of many, I think, of getting a flywheel spinning and leveraging kind of a unique advantage.
That you had in place and our goal is really to be the the most compelling tech company to work for in indiana and hopefully the midwest and that we'd be able to kind of win on talent and we'd we'd win on talent by providing really exceptional experiences for very young people and and often they could grow quickly and get more responsibility than they'd be able to working for a larger organization or perhaps a company in a different geography.
Ian Hathaway: Zooming out the macro on you as a person, as a leader, when I was thinking about what I wanted to talk to you about today, this word community just kept coming up. [00:42:00] It's sort of in your DNA and who you are as a leader, even going back to this decision to do something that a lot of people don't do, which is start businesses with family members, right?
It turned out to be very successful. Yeah. So it's, it's been a family affair, a community affair from the beginning. Part of it was intentional, but part of it is just, you know, sort of who you are as a leader. I think that was best typified by the orange culture that you created at exact target, you know, about treating people well.
It's just what stands out to me about you as a leader, that community and family are at the heart of everything you do. What might you say to other business leaders about embracing that as an approach to building a successful company?
Scott Dorsey: Yeah, thanks Ian. You know, my, I'd say probably favorite leadership principles is definitely.
All the writing and thinking around servant leadership or as jim collins wrote in good great level five leadership which [00:43:00] that always resonated with me that single is the book i read the most during my exact journey you know that pages were really well worn out and we even had jim speak at our user conference connections which is really special but.
Level five leadership is about a blend of just humility, but also drive and ambition. And I would say that was the special combination that we really worked to create at ExecTarget was a blend of kindness and humility paired with just ambition and competitiveness. And those two often don't fit together, but boy, if you can get those to snap together, I think you've got a pretty powerful combination.
For me, I found As I developed and grew as a leader that one of my strengths was just leaning into relationships. And it comes natural for me, but just caring deeply about people and wanting them to be happy and successful and kind of wanting them to love the company so much that they poured their extra time and effort into it.
And that they would want to serve our customers really, really well because they knew they were with a company and a set of [00:44:00] leaders that they could really trust. There's so many different leadership styles and there's not One style that fits all, but I think my advice to young and aspiring leaders is find a leadership style that's very genuine and authentic to who you are as a person and kind of leverage use your strengths.
Ian Hathaway: What was orange culture? Where did the idea come from and why do you think it's had this continual success, uh, this lasting effect in the community?
Scott Dorsey: Along our journey, we felt like we were building something special. We had a strong kind of tight knit culture and, you know, partners and customers and employees would really feel it, but we didn't have a great way to describe it and our CMO, Tim Kopp came up with really the brilliant idea of kind of creating a brand framework or an identity for our culture called orange or be orange.
Turned out to be one of the best moves we ever made because it, it brought color and identity to a feeling, you know, that all of us had. And when we were going through our real surge of hiring and doing [00:45:00] acquisitions and opening offices all around the world in, in a really special way, it became kind of a thread that knitted all of us together.
And, uh, and it took on many, many different life forms that, you know, give you a couple of quick examples are employee onboarding. Became called officially orange and any higher all around the world. You'd fly to Indianapolis, go through two weeks of training and really get kind of indoctrinated into our team and our culture.
We started investing in leadership development and that became leading orange and it really became kind of leading with heart and kindness and living out our core values. And what I really, really loved about orange is that we didn't mandate too strong of a narrative or language around what the culture meant.
We really left it open for everyone's individual interpretation. And I think, you know, you have a powerful culture when people feel it, experience it and kind of describe it in their own words. And then we'd live it out at our user conference connections and customers and partners would feel part of orange.
We've been at moments where we [00:46:00] land a new customer and I would get an email saying, Hey, I can't wait to be orange or I'm so happy to join the orange family. I would say our culture still lives on today, you know, over a decade longer than when the company even existed. So we, we have an orange culture today, even though exact target no longer exists as a standalone entity and a couple of ways that still gets carried forward.
We have a Facebook group called orange crush with a couple thousand members and people are posting. Several times a week, photos, pictures, career updates, life changes. We had a 10 year reunion where we threw a party here in Indianapolis, had a couple amazing bands. And this was so cool. And we had over a thousand people attend the reunion, many flying in from all over the world just to reconnect with friends and kind of relive that orange culture.
So that has to be one of the elements of the exact target journey. I'm most proud of is building a. a culture where people felt such a strong connection to one another, what we built, and then to see that [00:47:00] live on in a number of different ways is really, really rewarding.
Ian Hathaway: Yeah. And the, the impact of that, that those thousands of people are taking into whatever they're doing is immeasurable, but certainly it continues to make its way through the exact target community today.
And on the human level, the one to one, knowing that your company is, is led by someone, you know, a loving leader and someone who cares about your success is all too rare these days, unfortunately, but just kind of, I guess, zooming out on you, you've accomplished so much, but what are you most proud of? And then maybe looking ahead, what do you hope people will say about this whole affair and about the impact you've had 50 years from now?
Scott Dorsey: Yeah, thanks, Ian. I always describe exact target and I hope many other entrepreneurs have the same experience as. The gift that keeps giving and the reason exact target is the gift that keeps giving certainly seeing the salesforce tower Kind of shining bright and the landscape of indianapolis [00:48:00] feels good But more than anything it is absolutely about the people who worked at exact target Felt the level of closeness cohesiveness accomplishing something really significant together and how that became a launching pad For their career.
And if you look collectively at what the exec target team has accomplished, post et, it's just extraordinary. And there's literally not a week that goes by where somebody somewhere around the world doesn't reach out to me. Send me a little note, just thanking me for the exar experience and sharing what a difference it's meant for their family, what difference has meant in their life, and then what they're now doing professionally.
And it's really interesting. And when you think about. The good fortune i had of going from first time kind of scrappy founder to running a public company and everything in between you know i often think about mentors and investors and coaches who helped me grow but the other group that probably had the most profound effect were just the other members of our leadership team just [00:49:00] really talented people that i had the good fortune of working with and learning from and when we were In our later years of going public, I felt that we had an executive team of CEOs that anyone around the table could be CEO and would be a future CEO and many have like the legacy of where exact target alums are today is just extraordinary.
That's probably what I'm most proud of. And then also the, the ongoing impact in our community and next tech. We're going to hit our 10 year anniversary and we've been able to dramatically increase computer science education throughout the state of Indiana. When we started, we started in only 15 percent of high schools in the state of Indiana offered computer science.
15. Today. Every K 12 school in the state of Indiana offers computer science, and by 2028, it will be a high school graduation requirement. One of only four or five states in the country where it'll be a graduation requirement to take one CS class. That only happens with that kind of public [00:50:00] private partnership.
A lot of benefits that come from building companies in a smaller community. I don't know that exact target. Would have made much of a dent, you know, in San Francisco or Chicago, but in a smaller market like Indianapolis, you can feel the impact. And that it's very motivating.
Ian Hathaway: Well, and to me, that's the lesson, you know, I mentioned to you a big motivation for doing this series, this Outsider Inc.
was through the book, talking in communities around the country and around the world, and the prototypical question is, well, how do we become more like Silicon Valley? And my answer is usually some version of forget about Silicon Valley, learn about Indianapolis. And sometimes it's Where the hell is Indianapolis, but it's important for these emerging ecosystems that haven't had that success to learn about, you know, the long arc.
The requirements, the founder led dedication and the multifaceted approach it takes. It's [00:51:00] been a story that I've told in countless communities around the world. Hopefully we can build out a library of many stories like this that exist because I'm sure you know by now there are many of them. They just haven't been told enough.
But Scott, before we go, we like to finish each episode of Outsider Inc. with a segment. It's a series of quick hit questions that just helps the listeners get to know a little bit more about you as a person. Beyond the resume. Does that sound okay? Let's do it. Okay. So what's a quick piece of advice from a mentor that stuck with you throughout your journey?
Scott Dorsey: I think it's that first core value we had at ExactTarget was just treat people well. Just be a relationship builder, be kind, treat people well, and it'll come back to you in many, many unexpected ways.
Ian Hathaway: Who's an unsung hero in your life, and what's the impact they've had on you?
Scott Dorsey: Probably my wife, Erin, and she is remarkable.
We met in college at Indiana University, got married, have four amazing girls, and she is [00:52:00] just one of the most impressive people I've ever met in my life. Smart, disciplined, loving, encouraging, and brings out the best in me and likes me working hard. My underlying motivation is to make her proud and continue to Go out into the world and try to make a really positive impact.
Ian Hathaway: Yeah. Can't underscore that enough. How important it is for every entrepreneur to have a loving and supporting family behind them. So you grew up largely in the Midwest. How do you think your upbringing and maybe those Midwest values have helped shape you specifically as an entrepreneur?
Scott Dorsey: I think they did for sure.
We moved around a lot as kids. Ian, my dad worked for IBM. We moved every two years. So I think I learned how to embrace change, how to make new friends, build new relationships, be open minded to new surroundings. I think that had a real positive impact on me. And then I just think in many ways, going to school at Indiana and then at Kellogg and building companies.
And I have lived on the West Coast for a number of years, but I think I'm just a Midwesterner at heart. I try to kind of live out those, those Midwestern values. [00:53:00] I think of, you know, just hard work and humility and being a good relationship builder and looking for every opportunity to give back.
Ian Hathaway: Who's someone in your local community who doesn't get enough credit and deserves a shout out?
Scott Dorsey: You know, the person that comes to mind is a remarkable man by the name of Jim Morris, just passed away this last year. And Jim, Was an absolute icon here in the city of Indianapolis, CEO of the Lilly Endowment, number of different organizations, and most recently, Chairman of Pastry Sports and Entertainment, worked in Italy for five years, leading the World Food Program.
And Jim had more love for our community. And for providing opportunities for young people than anyone I've met just lived his life with a real servant's heart and also was a bold thinker and always looked to help people reach their full potential. So Jim's a mentor of mine who I'm going to miss, but he'll kind of continue to inspire me and many others in our community for a long time.
Ian Hathaway: Sounds like an amazing man. Tell us something [00:54:00] most people don't know about you. A hobby, a hidden talent, favorite travel spot, guilty pleasure.
Scott Dorsey: So I love sports and grew up playing golf, tennis, basketball, and over I'd say the last seven or eight years, I've become obsessed with a game called paddle tennis, not pickleball, paddle tennis, sometimes referred to as platform tennis.
And, uh, I love it. I've got a partner. We play tournaments kind of all throughout the Midwest. It's competitive, keeps me fit and sharp. And also it's played outdoors. So it helps winner go by much quicker than, uh, than they would. Otherwise I'm actually playing tomorrow. So that that's probably my hidden talent and secret passion.
Ian Hathaway: I'd never heard of that. So. We're building a founder's playlist. What are one or two songs you go to when you're kind of, that have inspired you, or maybe you go to when you're trying to jam on some work.
Scott Dorsey: Every year we had a user conference called connections. We are so proud to host it in Indianapolis.
We bring digital markers from all over the world into indie. [00:55:00] And our goal was always to land a, an artist or a band really before they hit it big and were very expensive, like outside of our price range. So our, our two most notable ones were. Train. We landed Train right before Hey, Soul Sister came out.
So that's always a favorite. And then, uh, and then we also landed Imagine Dragons. And, uh, On Top of the World was a song they played during Connections shortly after we were acquired by Salesforce. And that was a great moment. So On Top of the World from Imagine Dragons, that's an important song in my life.
Ian Hathaway: Well, that is the number one band in my family. My children love it and we listen to it all the time. So I'm so glad we're adding that to the list. Okay. Scott, last question. If you could give one piece of advice to someone who's about to start their first company today, especially someone who's a bit of an outsider like you, what would it be?
Scott Dorsey: Don't be afraid to ask for help. You know, really work on building your network. And reach out to people, you know, reach out to people, you don't know, and ask for [00:56:00] help. And that could be trying to find talent to build your organization, could be finding early customers, could be finding funding. I think generally.
People really want to help and give back. And, uh, I think my advice would be, don't be shy. Don't be bashful, build a network, reach out to people in a genuine and professional way, and I think you'll be surprised at how willing people are to chip in and find a way to be helpful.
Ian Hathaway: Couldn't think of a better note to end on Scott.
Thank you so much for joining us today. I really enjoyed this conversation and I can't wait to share it with our listeners.
Scott Dorsey: Thanks, Ian. Absolute pleasure.
Ian Hathaway: That's a wrap for today's episode of Outsider, Inc. A huge thanks to Scott Dorsey for joining us to share his incredible story and to help us launch this platform.
There's so much to take away from the conversation. Scott's community first and be kind approach to building businesses is truly an inspiration. And the foundation laid by his success in Indianapolis will be fun to watch unfold in the coming years. I hope that listeners everywhere can take these valuable lessons [00:57:00] And carry them forward into their own lives.
If you want more from Outsider, inc. Don't forget to subscribe to the platform@outsiderinc.substack.com. It's packed with highlights from today's episode and bonus insights you won't wanna miss. You can follow Outsider Inc on YouTube, Instagram, TikTok, and LinkedIn at Outsider Inc. Pod. You can also follow me on X at Ian Hathaway.
Outsider Ink is produced by Spellbinder Media. We'll be back soon with another fascinating outsider conversation. Until then, thank you so much for listening. And remember great entrepreneurs can come from anywhere. See you next time.