Most CEOs default to a familiar strategic instinct: if you’re not winning, execute harder.
Improve the product. Tighten operations. Increase output. Push the team.
Andrew Ackerman faced that moment at Dreamit Accelerator. The firm was respected. Top five in its category. Growing. But structurally behind incumbents with stronger network effects and brand dominance.
The internal question became uncomfortable:
Should we try to outrun competitors who were already ahead or stop racing them altogether?
This was a structural decision about positioning, customer definition, and organizational design. It illustrates a recurring tension for scaling CEOs:
When does improvement stop being the answer?
Dreamit operated in a crowded accelerator market dominated by entrenched players. The leaders had scale advantages that compounded:
In marketplace dynamics, advantage compounds. The best startups go where the most active investors are. The most active investors go where the best startups are. Breaking into that loop through incremental improvement is difficult.
The temptation in this situation is to refine execution: better programming, stronger mentorship, sharper recruiting.
But incremental gains inside a structurally disadvantaged position rarely change the outcome.
The deeper issue was positioning.
The pivotal decision was reframing the objective.
Instead of asking, “How do we move from number three to number one?” the team asked, “Is this the right race?”
Dreamit realized something structural:
There was supply on one side and latent demand on the other, but no structured bridge.
Rather than competing on the same early-stage accelerator model, Dreamit shifted to serving startups that were further along and built a program centered on business development with large corporate partners.
It required abandoning the default accelerator playbook. No traditional demo day. No geographic focus. A verticalized, industry-specific structure.
It also required organizational change. Recruiting different startups. Building relationships with Series A investors rather than primarily angels. Designing investor roadshows instead of centralized pitch events.
The decision changed who the customer was, how value was delivered, and what capabilities the team needed internally.
Once the lane was defined, execution mattered. But as Andrew put it, “The difference between trying to push your way through in a crowded market and having an entire lane to yourself — it’s night and day.”
Finding the empty track mattered more than running faster.
A recurring theme in Andrew’s operating philosophy is simple: even if you are convinced the market is large, you still need to validate how customers experience the problem.
In Dreamit’s case, the team engaged both sides of the market:
That discovery process revealed a misalignment between how accelerators positioned themselves and what corporate buyers could actually execute.
Many founders skip this step. They build first and validate later. The cost is time.
And time compounds risk.
Andrew uses a simple operational filter:
Before acting, finish the sentence:
“This is a success if…”
Without a predefined success metric, teams can:
Defining success in advance forces sharper thinking.
It also frequently reveals that a cheaper, faster test can produce the same learning.
Once you know what success looks like, you often realize you don’t need the full build to evaluate the hypothesis.
For scaling CEOs, this is less about lean startup orthodoxy and more about resource discipline. As organizations grow, ambiguity increases. Experiments multiply. Without clear success criteria, teams burn cycles that look like momentum but produce no decision.
Strategic repositioning solves structure, operational clarity solves speed, but competitive advantage requires focus.
Andrew’s view is direct: “You only have to be great at one thing.”
Startups often attempt to win through cumulative marginal improvements. The assumption is that aggregate improvement creates advantage.
It rarely does.
Winning companies are meaningfully superior at a single critical capability. Everything else must be good enough. Nothing can be broken. But only one capability needs to be exceptional.
He frames it through fragility: a startup is like a chain. If one link is broken, the whole system fails.
This perspective sharpens executive prioritization:
Without that clarity, teams diffuse effort across too many fronts and dilute advantage.
Underlying the entire episode is a quiet but consequential insight: speed is not about urgency. It is about survival.
Time erodes optionality. It compounds capital risk. It increases competitive exposure.
Repositioning early, validating assumptions quickly, defining success criteria clearly — these are not tactical improvements. They are structural protections against time decay.
For Dreamit, redefining the lane accelerated momentum because they were no longer fighting structural headwinds.
Execution improved because positioning improved.
The most important decision Andrew describes was not about execution quality. It was about abandoning a race that could not be won on its existing terms.
For CEOs operating in competitive markets, three questions emerge:
Sometimes the pivotal decision is not how to win the race.
It is whether to run it at all.
For a deeper look at how Andrew made that call — and how he thinks about discovery, speed, and strategic positioning — the full episode offers additional nuance.
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Andrew Ackerman is the Founder of SCV and a former leader at Dreamit Accelerator. His career spans consulting, startup operations, venture investing, and corporate innovation. He has worked across multiple stages of company building, giving him a broad perspective on how CEOs navigate structural constraints and strategic inflection points.
Learn more at https://www.scv.vc/ or connect with Andrew on LinkedIn.
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Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
Transcript Summary
Full Transcript (AI generated and might include errors)
Jeff Holman (08:08.245)
Welcome back to the Breakout CEO Podcast. I'm your host, Jeff Holman. And today I've got Andrew Ackerman with me. Andrew's lived what I think might be the full arc of entrepreneurship, scaling a company, leading another company that
maybe didn't work out as well, and then spending a lot of time investing, advising, accelerating other companies. I'm really excited to have this interview today. Andrew, welcome to the show.
Andrew Ackerman (08:48.594)
Thank you, thank you for having me.
Jeff Holman (08:50.486)
Yeah, it's exciting to hear and see people who've done a depth of different experiences. Do you have a theme to this arc that you've been on? And maybe you didn't have it up front, but looking back, are there any overriding themes to what you've been doing?
Andrew Ackerman (09:09.412)
Yeah, you know, it seemed like a good idea at the time. No, so I, I mean, all of people who were at least it looks like, like they, called their shop from the beginning. was like this, that, and the other thing, especially when it was like, like sort of different basis to get around to where they wanted to be. And I was wondering to myself, like, did they really plan that from the beginning or did it just kind of come together nicely for what they want to do? And in my case, it's definitely been in that other category. And when I started out.
Jeff Holman (09:12.43)
I love that.
Jeff Holman (09:26.734)
Yeah.
Andrew Ackerman (09:39.741)
There's no, like this whole startup scene didn't really exist. So was a consultant for four years, but I actually got some really interesting skills out of that. And then when all of a sudden, like the startup things for real, right. And then the bloom is happening and I get into my first startup and I do that for eight years. That's awesome. Then when I'm coming out of that, I ended up in a family office. So I'm kind of on that side of the table. And that was an interesting experience. I did my second startup, which as you alluded to,
Jeff Holman (09:45.186)
Yeah.
Jeff Holman (10:05.132)
Yeah.
Andrew Ackerman (10:09.04)
Well, experience is what you get when you didn't get what you wanted. That was an awesome experience. no. And then I ended up doing more and more investing. So then I shift over to another part of the table as an angel. And then ultimately as an accelerator or a VC. So when I look back and I'm like, wow. The stuff I got in consulting really helped me with dealing with the corporate customers that I wanted to get from my startups. And then it helps me understand why a corporate venture fund works or doesn't work. Like, yeah, it all adds up.
Jeff Holman (10:11.66)
Yep,
Andrew Ackerman (10:38.802)
You know the temptation is to say yeah, I purposely did that I wanted all those building blocks where the truth is like no No, there was kind of a step level progression with a little bit of luck a little bit of interest And now the things I can do are the sum of those experiences But I'd be line if I said that like this is the plan all along
Jeff Holman (10:51.107)
Yep.
Jeff Holman (11:00.846)
Totally fair and I can relate to that myself with my own journey. You know, if you asked me when I was 15 or 16, what do you want to be when I grow up? My answer was simple. I want to be rich. I had no plan to get there, you know, and I've done fine for myself, but I think life and the journey happens to you and there's, while there's a certain skill that allows some people to dictate and follow that path really easily.
Andrew Ackerman (11:12.294)
Mm-hmm.
Jeff Holman (11:28.942)
I think there's a certain skill to flowing with the path as it develops too. And that's worked for me and I think it sounds like it's worked very well for you too, to be able to draw from all of that. So if you look back at this experience as it unfolded, what are the two or three highlights that maybe carry the most weight for you for where you're at today? That maybe the things you've pulled to
Andrew Ackerman (11:40.786)
So far so good.
Jeff Holman (11:58.69)
to aggregate into the skillset you have.
Andrew Ackerman (12:01.794)
That's a good one. There are a couple of moments along the way where I learned things and sometimes how, know, how formative they would be wasn't clear to me at the time. So during my first startup, and we're really early, this is a company called Bunk1. We're doing a internet services for summer camps, password protected photo galleries, one way email systems. You know, the kids don't have to be anywhere near their computer. It's printed out and given to them.
Jeff Holman (12:26.2)
Okay.
Andrew Ackerman (12:29.938)
I know it seems pretty basic, but in 2000, that was a big deal. I had just come out of consulting and I'm having a little bit of trouble with one of the salespeople because every deal he has is different. It's like 9.95 for this guy. It's 9.99 for that guy, 9.98, $10. I'm Ed, man, the f*ck? Pardon my language, but like really, can't we just all have the same? And it got to be a bit of friction. Like the spreadsheets were getting unwieldy. I couldn't run any of the numbers.
Jeff Holman (12:33.357)
Yeah.
Andrew Ackerman (12:58.546)
That's not strictly true. could, but it was, it was untidy until the CEO took me aside and says, Andrew, you don't get it, right? We're early in this whole journey together. Right now we just need to say yes. Right. A we need the money. B we need the customers to refer to so we can get more of them. But more importantly, like we need to get as many customers on so we can learn from them so we can understand like what they really need so we can make our product better and make new products. So right now we're just saying yes.
Jeff Holman (13:02.125)
Yeah.
Andrew Ackerman (13:28.816)
And maybe when we 10 X the revenue, then like the complexity is a problem. So go in there and clean it up. But like for now, the number one thing we need to do is make it possible to say yes. And that's when my mentality kind of flipped, right? That's like, get it now. Startups are messy. They're supposed to be messy. It's supposed to let you learn from things you didn't think you would come across. And the time to like smooth it out is as you scale.
Jeff Holman (13:28.898)
Okay.
Jeff Holman (13:41.528)
customer feedback.
Jeff Holman (13:57.282)
Yeah. And were you able to, was Bunk1 able to smooth it out, scale, figure out what the, what the customers wanted? Did that turn out well?
Andrew Ackerman (14:05.316)
Yeah, absolutely. We did about two or three years later, don't remember, two or three years later, we did a pricing rationalization project. Yeah.
Jeff Holman (14:13.664)
Okay, so you got to the point where you were able to introduce some order to the chaos.
Andrew Ackerman (14:19.792)
Yeah, yeah, absolutely. And the second time where it was kind of formative.
So we were, and this was kind of one of the points we talked about earlier about kind of those breakthrough moments when you're kind of at a plateau and like, you know, how do you get back up until like that strong and to the right growth, up and to the right growth. So I had been at Dreamit, which at the time was one of the top five early stage accelerator programs in the world. And for those people in your audience who aren't familiar with accelerators,
Jeff Holman (14:36.984)
Mm-hmm.
Jeff Holman (14:43.085)
Right.
Andrew Ackerman (14:56.158)
it is the kind of investor that gets involved even before a venture capital fund does when the startup is, you know, not quite fully baked. and it helps them get to the point where they can raise what's called their seed route, which is usually their first, meaningfully large check. So
Jeff Holman (15:05.485)
Yeah.
Jeff Holman (15:12.664)
Yeah. And you're really stepping in to say, hey, maybe there's some money involved, but we have usually a core team that can fill some of the gaps and provide some of second time founder experience to the first time founder who's in the accelerator, right?
Andrew Ackerman (15:24.496)
Yeah.
Andrew Ackerman (15:29.298)
Absolutely. Like it's, um, it's a very high touch experience. All the programs are a little bit different. The way we did it was we'd meet with the teams weekly, but go in depth every week for an hour or more. Where are at? What are they going to do next deliverables for next week? And parallel, we bring in speakers on a bunch of different topics, you know, so it's like pizza's here, speakers here, sit down and learn. And at the end of that 12 week period, they'd be like a get up in front of like a bunch of investors and pitch your heart out for money type deal.
Jeff Holman (15:49.826)
Yeah.
Andrew Ackerman (15:59.379)
So that's the general outline of like an early stage accelerator. And that's what we were doing for like the first couple of years I was there. Uh, I was about two, two and a half years in and we had this offsite, but with a new CEO and the CEO was like, eh, being top fine is top five is fine. But I really want to be number one. Can't we be number one at what we're doing? So kind of sad. Uh, at the time it's still, so why commentators still number one, they were the first and, uh, the oldest one. They have a fantastic.
Jeff Holman (16:05.39)
Mm-hmm.
Jeff Holman (16:21.592)
Who were you competing against at the time, just for context?
Andrew Ackerman (16:29.25)
and I can quibble a little bit about like it's become a puppy mill and like a little bit of lemming like, you know, investing process, but they still like, they built something awesome and it's true. and then, you know, arguably the next one, certainly at that time was Techstars. they built a very large network of accelerators, many of whom, or most of them were funded by corporate partners. we tried doing that too. We had some, but like they were better at it than us.
Jeff Holman (16:30.104)
Mm-hmm.
Jeff Holman (16:54.657)
Mm-hmm.
Andrew Ackerman (16:59.122)
No doubt hands down. So, you know, there were others out there, but we were that's those were kind of the big two and we thought like maybe if we did everything right and we executed on everything just right and maybe if texture stumbled a little we might be able to overtake them But my comment was too far ahead. We just didn't think that was gonna happen because it's a little bit like a virtuous cycle like a marketplace
Jeff Holman (17:05.902)
Okay.
Jeff Holman (17:22.69)
Mm-hmm.
Andrew Ackerman (17:24.114)
the best startups want to go where they, they're the most active investors and the most active investors want to go where the best startups. And if that's Y Combinator, that's where they're going to go. It's like any marketplace. So, you know, we had this, this conversation at our offsite and, the CEO at the time, our great guy. He's like, well, I don't want to be number two or number three. So what can we do where we can be number one? And just changing the way we thought about it from like, you know, how
You know, how can we like maybe move up in the ranks to like, what could we do? like, we're not butting up against these guys. Got us thinking, well, you know, we actually do have some interesting supply and demand dynamics of our own. We've got all these later stage for us startups. So after there's seed round startups and that we really love the way you get startups, you know, introductions to potential corporate partners. But we're like beyond this stage. Is there anything we can do that may be a little different?
and then on the flip side, had a lot of the corporate partners that were saying, man, that's really interesting. Like that's a great, interesting startup, painful problem, great team. love what they're building, but they're just a little too early to work with a fortune 500 companies. So we're to watch them for six months to a year. And like, like idiots, we kept bringing them, you know, early stage stuff and they kept saying, that's awesome. But six months, but keep bringing us the cutting edge stuff.
Jeff Holman (18:34.455)
Yeah.
Jeff Holman (18:41.006)
Okay.
Jeff Holman (18:44.558)
Thank
You're yeah, you're the accelerator and they're saying, wait, slow down, not accelerate, slow down. Yeah.
Andrew Ackerman (18:53.938)
Well, they weren't saying that because they didn't even know it, right? They like, we want cutting edge, but we're not ready to do it. And they didn't really, it's almost like the dog chasing the, you know, the mailman, like, and if you capture the, if you catch the truck, what are you going to do to it? Right. They didn't kind of thought that through, but then it dawned on us, wait, we have later stage startups who are six to 12 months further along. And we have the corporates that want to meet them. Let's make that market instead. We ended up saying, well, if we do that.
Jeff Holman (19:07.298)
Right, right.
Andrew Ackerman (19:22.992)
Like, you we can go a little later. There's nobody doing that. Number one, we're the only one. there's just two problems. one we have to change the entire program and B we have to change the entire financial offer. We're like, heck that's a how that's not a lot. We can do that. So yeah.
Jeff Holman (19:34.626)
Yeah. Small, small. Yeah. Well, I want to back up though, cause you're, what you're, what you're explaining is, you know, the, sounds like the initial goal was, Hey, let's be number one, like categorically number one. And then, and then the team said, wait a second, that might be a little bit difficult to do given the circumstances. Let's be, let's be more blue ocean, you know, number one in a way, let's define where we can be number one, even if it's not.
Andrew Ackerman (20:02.674)
Well, let's let me, let me give a slightly different analogy, right? So, um, you know, imagine you're racing cars, right? I mean, F1 was out as well. had that long ago, right? So there's a bunch of cars in front of you and like you're jockeying for position. Can you pass them? You know, they got to make a little bit of a slip up and you got to get past them. Well, like, you know, it's really hard. Now what we did instead of like, you know, F that track, we're to go on this track and there's nobody on that track.
Jeff Holman (20:03.982)
across the board. Yeah.
Jeff Holman (20:30.499)
Mm-hmm.
Andrew Ackerman (20:31.452)
So there's no one we have to worry about getting in front of this, no one blocking us. Like we're out. And the difference between trying to push your way through in a crowded market, even if you're doing reasonably well and having an entire like lane to yourself, it's night and day. Well, you got to start thinking about your business differently. You to start thinking like, I'm, you know, this is what I am, but wait a second, I don't have to be that. What if I was this instead? And you know,
By challenging us the way he did, he got us thinking rather like, how can we get ahead of the next car to like, where can we find an entirely empty lane?
Jeff Holman (21:08.844)
Yeah, which brings along with it the challenges like you mentioned, you have to start building the track or identifying the lane or maybe modifying your car so it drives on a different surface, whatever, right?
Andrew Ackerman (21:21.532)
Good news is you have your own lane. The bad news is it's a river. Okay, so we'll build a boat instead, right?
Jeff Holman (21:26.19)
Yeah, yeah. And who's the audience at the track and, you know, who are you catering to at that point?
Andrew Ackerman (21:31.634)
The new network of later stage investors, right? That was more important. We had to get rid of that demo day. Cause like, if you're trying to raise a series A round, like you're trying to raise five or $10 million instead of like two or three, right? The different type of investor, different type of raise. And there was a lot of changes we had to make and without going into too many details, it was a lot of fun to do it. But the key is like, once you figured out where that lane is, then it's execution. Like it's important.
Jeff Holman (22:00.579)
Mm-hmm.
Andrew Ackerman (22:01.317)
but it's not as important as finding that lane.
Jeff Holman (22:05.506)
Well, did this end up being an inflection point for Dreamit? Is this, was this the transition from Dreamit 1.0 to Dreamit 2.0?
Andrew Ackerman (22:09.98)
absolutely, absolutely.
Yeah, no, absolutely. It was. So we were, uh, we, at the same time, one of the things we did is we went vertically focused. Cause you were going to hang your hat on biz dev. It's easier to do that for like, you know, five or six companies or seven companies that are all in sort of the same industry. And they all have like the same group of maybe three potential, uh, or four potential types of customers. So we did that and we went from being like nothing in, in the spaces that we opened up to being the leader.
Jeff Holman (22:21.26)
Okay.
Jeff Holman (22:34.68)
Mm-hmm.
Andrew Ackerman (22:43.523)
in that space virtually within a year or two. It was very easy for us to capture attention because when no one else is doing it, like, my God, they're the only ones doing this.
Jeff Holman (22:47.362)
Go on.
Jeff Holman (22:54.702)
What did that do to your, I wanna say audience again, but being more specific here, what did that do to the network you were in? Like what did it look like before the transition? then how was it, you were leading in the next one, but what was that change?
Andrew Ackerman (23:09.769)
Yeah. So let's, let's talk about a couple of audiences, right? So we had the startup audience, which these are, you know, they come into the program. Then we had the investors who hopefully would invest in the startups. Then we had the corporates who would hopefully do business with them. Let's just start with those three because there's a couple of the smaller ones, but, uh, number one, I had to go off to different pool of startups. Right? So I was recruiting initially generalist earliest stage, you know, when you're just a couple of guys, you haven't raised any money. There's not a lot of digital footprints.
Jeff Holman (23:13.869)
Mm-hmm.
Andrew Ackerman (23:38.033)
So you got to do a very strong ground game. You got to go to events physically. You got to partner with groups that have co-working spaces and the such.
Jeff Holman (23:47.65)
What year was this by the way? Cause that changes.
Andrew Ackerman (23:50.239)
so when I first came in, it was 2014 and we'd been doing that since 2008.
Jeff Holman (23:54.946)
Okay.
Andrew Ackerman (23:56.946)
So that was a tough ground game, but then you're starting to deal with startups that are a little further along. You can start doing things like, well, I'm going to go subscribe to Crunchbase or Mattermark. And I'm going go figure out who's raised a seed route. Has it been eight months, 10 months, 12 months since that seed route? They might be in our strike zone now. We can start using those as indicators, not a hundred percent, because in the fields that we were in, there were a lot of people that kind of bootstrapped beyond it, but we could do that.
Jeff Holman (24:07.501)
Mm-hmm.
Jeff Holman (24:16.567)
Yeah.
Andrew Ackerman (24:26.181)
And along that, had a kind of another challenge, which was all of our startups, when they heard the word accelerator, the ones that we wanted to meet with, we're beyond that stage. But that actually meant that they were at our stage. They just didn't know it because they thought we're an accelerator. So we had to change how we communicated it. Like we didn't use the A word anymore. So the startup side changed. And then for the investors, like instead of going after angel investors who like to invest a little bit more locally,
Jeff Holman (24:38.722)
they thought about accelerators differently than.
Jeff Holman (24:45.057)
Okay.
Andrew Ackerman (24:53.137)
I'm bringing them into a room. We're going after series A investors, which are usually VC funds or corporate venture funds. They will often invest nationwide, sometimes internationally, but they have like their own special focus, foci, that'll work. know focuses. Okay. I'm going to a foci. They have their own foci and you have to understand all of that. a lot of general angels are calling, Oh, show me a shiny toy. Let's see. So we had to develop a much more structured version of the list.
Jeff Holman (24:59.276)
Mm-hmm.
Jeff Holman (25:08.462)
Yep, that's a word.
Andrew Ackerman (25:21.989)
by geography and we actually had to go with our startups. We call it a road show, right? We do the investor road show. We go take them on the road with them. Yeah. We had to be very purposeful about that. And we were early adopters of Zoom pre-pandemic for the cities we didn't go to. So we had to build all that different network of investors. And we had to think about how we access them, right? They, you we had a plan ahead and demo day didn't work. So we threw it out and we came up with the investor road show instead.
Jeff Holman (25:26.73)
Mm-hmm, with them.
Okay, okay.
Jeff Holman (25:37.155)
Got it.
Jeff Holman (25:50.626)
How did this change how you're like the dynamics of your team? Because, you know, when you change the business model necessarily team dynamics shift roles change functions change.
Andrew Ackerman (25:58.93)
Absolutely. So, at the core level, right? you we used to be geographically focused. changed to being industry focused or vertically focused. Okay. That's fine. I've done a lot of things in my, my career. just spanned up an ed tech program and then later I spanned up, you know, prop tech and construction tech. it was fun kind of learning about it.
Jeff Holman (26:14.574)
Mm-hmm.
Andrew Ackerman (26:25.991)
but also now instead of being like, okay, I'm running program that I'm going to like, do other things and run another program instead of flexing up and down. It became much more of a year round program. So I had a team with two other people in my vertical. and we had one that was more focused on program managing and we had another that was focused on kind of the early stage prospecting. Like let's find those, let's get in touch with them, set up the meeting, make sure at the right stage, and then bring them to me.
Jeff Holman (26:47.662)
Mm-hmm.
Andrew Ackerman (26:53.477)
So we became a little bit more disciplined about that, know, slightly different skills. By the way, I'm one of those people that says like, you know, people out there like, A plus people only work with A plus people, right? Only hire A plus founders for your team. And I'm one of those people that says, yeah, of course, if you can, but you know, resources aren't unlimited, right? So, you know, anyone can make an awesome hamburger from Kobe beef, but the whole idea of
Jeff Holman (27:14.766)
You
Jeff Holman (27:21.72)
Yeah.
Andrew Ackerman (27:22.769)
creating the hamburgers that you can take the less than perfect meat and still have a really good meal out of it. So, you know, the skill as a founder is understanding where you need to be awesome, right? Where you need to, you and your co-founder have to have these two skills or two areas of expertise down, and then you need to be able to get the best effort out of everyone else just to keep things going and moving forward. So I think it's a myth that you can like,
Jeff Holman (27:28.493)
Right.
Andrew Ackerman (27:50.034)
recruit A players all, I mean, unless you're going to raising $50 million, like pre seed rounds, because I don't know you're open AI, but I digress. So the team shifted a little bit. had to specialize, work at those school, those processes. And then we also had, instead of being like a whole bunch of individual little fiefdoms by geography, we had to have people kind of more the lack of a better word, corporate level or the central level, coordinating all the moving parts. So we would have
Jeff Holman (27:57.174)
Yeah, yeah.
Andrew Ackerman (28:19.855)
A health vertical, would have, you know, prop tech and construction tech vertical. would have a, secure tech vertical and we would all have the investor road shows at the same time. So we needed basically people that can run those events like, Hey, because some of the investors are general. they'll look at everything and more industry specific. it's like, okay, these two weeks we're on the road. We're going to be in the Bay area these four days. You know, here is.
your list of four or five prop tech companies, or here's your list of 15 companies across all the sectors. So we had to build that, those capabilities at our kind of corporate level.
Jeff Holman (28:57.966)
Was there ever a moment where the team expressed or maybe just acknowledged that? Because it sounds like as you shifted your business model, you're building out functions to match the model. And in a sense, you're kind of doing the same things in a way that you're seeing your accelerator companies.
doing in their own businesses, right? You're building as they're building, so to speak. Was that apparent or was that a factor in how you guys did things?
Andrew Ackerman (29:29.615)
Yeah. Well, that's what kept it exciting, right? Cause like, you know, we do something once, okay, work, we do it again to get better at it. And then the third time, like, you know, screw that, we're going to tear it up and do it totally differently. You know, it's a very startupy way to do that. And you know, I'll give everyone I worked with credit for eating their own dog food on that. no, it's a little different, right? We had different customers. had different type of marketplace, but at the, like the meta view, the highest view, right. You got to go out there.
Jeff Holman (29:54.478)
Mm-hmm.
Andrew Ackerman (29:57.158)
You got to get a list of prospects. got to qualify them, right? You got to move them through the funnel. You got to close them, right? You got to think about that kind of systematically and objectively. You got to have that kind of framework about going into the world and into the market.
Jeff Holman (30:12.086)
And you were in a sense testing product market fit with this new approach to see if it worked for the different audiences that you were working with. kind of wonder, does it make, does it ever raise questions? Cause I think when I relate this back to CEOs who are building a business and they're in this messy muddy stage, right? And they're like, some days it's like, we're killing it. This is awesome. I think we've got it down. And the next day they're like,
Andrew Ackerman (30:33.798)
Mm-hmm.
Jeff Holman (30:41.686)
man, we really messed up. Like, I don't think this is gonna work. What was I thinking? Like, was that ever present at the team level with you guys? Because it's what CEOs relate to in a way. And it's hard to build a business without having some of that, right?
Andrew Ackerman (30:55.793)
and
So I'm tempted to say like, was like that every other Tuesday. but actually it wasn't, it wasn't, early on it was, but it got a lot better. let me, let me kind of break that down for you. first time founders and the early generations of accelerators ourselves included kind of make, many of us make a similar mistake. Right. We see a problem in the market. That's huge. Right. We know it. It tinkered with two of that. I got it. Like it's definitely big. There's no.
Jeff Holman (31:05.097)
Andrew Ackerman (31:29.893)
denying that and we come up with a solution. We call them just build it and put it out there. And that's actually wrong in two or three different levels. So number one, even if we're convinced that it is a huge market and like it's a big problem, you gotta get out there and talk to a lot of people. Because even if you're right that it is a huge market, going out and talking to all your potential customers or if you have a marketplace like us, both sets of your customers are all three sets of your customers, startups, investors, corporates.
Jeff Holman (31:45.804)
Yeah.
Andrew Ackerman (31:59.228)
You have to understand how they see the problem. So number one, you'll validate there is a problem and that's big. And number two, you'll also understand how they see the problem. you understand how to design what you're building. So the other reason it was wrong, we just went out there and built, like you want to get that feedback before you build as much as possible so that you don't end up building stuff no one cares about, or you don't end up building it in ways no one understands how to use it. So I talk about this in my book a lot.
Uh, with a couple of different analogies, like the, index card app. let's say, let's say I wanted to build like a, app for, you know, for whatever. Uh, lot of the first time founders go in there they're like, okay, I know what I want to build. I'm going to go down, put my hoodie over, go into a dark room and I'll just code for four months and boom, here it is world. Enjoy it. And then they find out that like half of the features, no one touches the other ones. No one knows how to use. And they go back and they fix it. Um, for the cost of.
Jeff Holman (32:30.072)
Mm-hmm.
Andrew Ackerman (32:55.761)
like a pack of four by six index cards. I don't know what's that, like five bucks and a pen, which by the way, you can steal from your local bank. You don't have to pay for this because startups should be cheap. You know, there, and you sketch on a bunch of the cards, what each page in your website or your app looks like. Crew drawings, right? No, this is not just basics. Yeah, I mean, you could use, I use balsamic sometimes, but then that mocks like the hand drawn look to it.
Jeff Holman (33:15.638)
Not even even figma at this point.
Jeff Holman (33:23.382)
Hmm.
Andrew Ackerman (33:23.845)
But you want to come up with all these pages and then you go out there and you talk to 30 people, 20, 30, 40, 50 people who are your target customer. And you say, thank you so much for agreeing to do this. What I want to do is I want to put a mock-up of my, my app in your hands. What I want you to do is I want you to interact with it. Exactly the way you would interact with it. If it were really on your phone right now. So if you want to swipe, swipe on the index card and I'll give you the next screen tap swipe.
If you're not sure, just, well, that's the one thing want you to differently. You can't ask me questions because I'm not going to be there when you download it. Just verbalize what you're thinking because I can't read your mind. It's like, oh, that's cool. Say that out loud. Or I have no idea what that button was and is and I'm afraid to push it because who knows? I just got to say that out loud. But otherwise, I'm just going to watch you and let them interact with it, them the new screens. And then, know, 20, 30 minutes later when they're like done.
Then you break character and you debrief and you're like, hey, I noticed you didn't use any of these. You know, why not? So I don't need that. Right. Or, you know, I noticed you hesitated over here. What's the deal? And, know, kind of debrief with them and get that. But if you do that for like 20, 30 or 40 potential customers, when you actually go out there and spec out your product and build it, it's going to be a lot smoother. You're not going to build the stuff. No one wants the stuff that people want. You'll build the way they want the way they understand it. You won't miss anything.
And that was in essence, the difference between Dreamit 1.0, where we're all just kind of figuring it out. We went out there, built it, iterated. Dreamit 2.0, where we spoke to a whole bunch of startups, in the later stage, like, would this make sense to you, right? We spoke to a whole bunch of the investors. We spoke to a lot of the potential customers. And we, know, the right way, right? the old saying, like, if you ask somebody in the late 1900s, sorry, 1800s,
Jeff Holman (34:56.257)
Mm-hmm.
Andrew Ackerman (35:17.335)
know what they want, they're like, I want a faster buggy, right? They wouldn't think of the car. So you got to kind of get at those, you know, those ideas. But we spoke to a lot of them. We validated and understood what really mattered for them. So then when we finally built it, like it just worked better the first time. Now there was tweaks, right? There were tweaks, but we got the overall blueprint, like I would say probably 90 % right coming out of that discovery. And that's like the
Jeff Holman (35:20.172)
Right, right.
Jeff Holman (35:33.571)
Yeah.
Jeff Holman (35:43.416)
Wow.
Andrew Ackerman (35:44.699)
For me, that's the number one thing that separates a first-time entrepreneur from a repeat entrepreneur is they don't just jump right in. They test it very quickly. They do their discovery. And it makes all the difference in the world.
Jeff Holman (35:53.069)
Yeah.
Jeff Holman (35:58.978)
Yeah, there's still maybe a final gut call or instinct, but it's based on data at that point. It's based on tons and tons of feedback. Did you guys find that this system should work not only for Dreamit's reconfiguration, but did you find that you were dealing with startups at a stage that could still benefit from this same model and implement it at the stage they were at?
Andrew Ackerman (36:03.705)
Yeah, so you can't get everything.
Andrew Ackerman (36:26.225)
That's funny. Right. So earlier on when we were in Gmail 1.0, it was hugely valuable. Right. We can go in there and be like, it's actually a really great story. tell a lot about a company that I'll tell you the short version of it. It was a company that, um, had built the free features, but hadn't built their premium features. So they were like, okay, listen, we're going to spend the next two months building it. And then we'll have it. It'll be two weeks before demo day. We'll roll it out. We'll get the data and we'll pitch. And then we're like, well, what happens if.
The data is not good. What happens if the conversion rate is too low? And like, that would be bad. So we said, how about this, right? We're going to put up, you're going to put up the upgrade now page, right? You know what you want to build. You know what you want to price it at. Just put it up there. And anyone who clicks it, you go, coming soon. I had one company that why did it? their problem was they didn't have a merchant account. So they even took the credit card information. It never left the person's computer.
But to them, it looked like he was actually purchasing it. And the reason they did it is it got them clean data on what the uptake rate was going to be from like free to premium. And they could do it in like an hour or two, or they just put the page up. So then they did that. And next week they're back and like, yeah, we're screwed. The rates are way too low. Yeah, it didn't work. Yeah. And it didn't work.
Jeff Holman (37:24.995)
Mm-hmm.
Yeah.
Jeff Holman (37:46.235)
It didn't work. Free conversions, high paid conversion is non-existent sometimes.
Andrew Ackerman (37:53.965)
in such a dramatic way, there was no way they could tweak their way up to it. And then they kind of sheepishly said, but you know, this is one part of our site where like a lot of people are engaging and we think we could build something different around this. You know, can we do that? And we're like, well, if this is a zero and that might not be as your sure, go ahead, do that, please. That's the whole idea. So they ended up doing it and it worked. And that company is now SeatGeek. So it's a billion dollar company, a unicorn.
Jeff Holman (38:21.862)
wow.
Andrew Ackerman (38:23.992)
that had they done the archetypical first founder, let's just code it and see what happens, would never have existed. Now, the reason I said it's ironic is because then when Dreamit went one stage later, most of the founders that we spoke to had either figured that out or already failed by doing it the other way. So that kind of impact would be less dramatic. But we did have, we had a saying internally,
Jeff Holman (38:44.878)
Okay.
Andrew Ackerman (38:53.316)
that we did and that we shared with our founders, right? Before you do anything, finish this sentences. This is a success if. Right? So if you're going to go out there you're going to test building a new feature or you're to test like a new marketing channel, how do know it's a success? Drive it down to like a number you're going to measure or certain outcomes that you want. Cause if, if you don't have that, you'll go do it. And then in two months, you'll come back and look at it and be like, wait, I don't really know what I proved here.
Jeff Holman (39:23.316)
I have data, but I'm not sure if it's good or how to use it or how to make a decision from it.
Andrew Ackerman (39:23.598)
And what's your number? I don't know.
Andrew Ackerman (39:29.25)
Exactly. And then once you know, like, this is what success looks like, it sometimes leads you to think, well, do I really have to do all of this? Or is there a way I can do it much faster, much cheaper, maybe even for free and get at the same number and I don't have to do all of this. So it changes the mindset and it just makes everything faster and, know, in time, time kills startups. So you can do things faster and cheaper. You're just, you're just loading the dice. You're just loading your favor at every stage in the process.
Jeff Holman (39:54.018)
Yeah.
Jeff Holman (39:57.314)
Yeah, it really focuses the mind. was telling my law firm staff just this morning about an experience where I was talking about achieving something and I said, but instead of just going out and doing it, what I did is I said to myself, I'm going to put a goal to it. So I wrapped it kind of like you're talking about. I wrapped it into this context and I said, I'm just going to put a goal to it. And literally within five minutes of naming a goal, instead of just an accomplishment, I started saying, wait.
Andrew Ackerman (40:15.024)
Mm-hmm.
Andrew Ackerman (40:23.631)
Yeah.
Jeff Holman (40:26.434)
why don't I do this? And my mind started connecting things that hadn't been connected before. I'm like, there's real power in putting the right context around these things.
Andrew Ackerman (40:30.5)
Mm-hmm.
Andrew Ackerman (40:37.764)
Yeah, absolutely. that's also, by the way, that's a whole about the way I turn, I'm going to shift sideways a little bit and put my corporate hat on. So like when I, talked about the programs that we do with corporate or when I do like, I also do a lot of, consulting for corporate innovation groups and corporate venture funds. Right. I talked to him, like how you talk about something and how you measure it. Like you get what you measure. Right. So, one of the subtle mistakes they make, is I'll ask you like, so
How is that pilot coming along? And if you ask that question, that way the answer has to be, it's awesome. Like, that's awesome, no problem. And they'll start throwing more more resources into making it a success until it is a success. But is it really a success if it took nine months and four times as much money as you thought? Or until they've been promoted and it's not their problem anymore. Whereas if you ask them instead, hey, how's the pilot coming along? Are they the right?
Jeff Holman (41:14.318)
Always.
Jeff Holman (41:25.987)
Right.
Andrew Ackerman (41:36.485)
company for us to be working with? Or should we be looking somewhere else? Or is this the right approach or should we just cut it and try something else? All of a sudden, iterating fast and getting to the answer is a win. And it changes how people think about it. It gives you permission to say, Andrew, we tried it. It looked great. Once we started working with them, those guys are impossible to work with. Let's go find somebody else.
Jeff Holman (41:51.341)
Mm-hmm.
Andrew Ackerman (42:04.868)
Great, you figured that out in three months. Awesome, let's go find somebody else.
Jeff Holman (42:09.706)
You gotta do that faster, you don't, or you can't exist long enough to find success, right?
Andrew Ackerman (42:14.352)
Well, large companies, because they have all their other strengths, they can drift on and they can do things slowly like that. It won't kill them usually, but it's even better for them. But the point I was trying to get at is just naming that goal and being very thoughtful about what that goal is, whether you're a startup, an individual, or even more so a large company, it makes a big difference.
Jeff Holman (42:36.546)
Yeah, yeah, that makes sense. guess I was putting that back into the startup context of existing long enough to find success. But in the corporate setting, sometimes the most negative aspect is you can persist forever in the wrong direction, right?
Andrew Ackerman (42:50.608)
or you used to, right? One of the slides I give to the entrepreneurship class I give, I do one a year, is this chart. And it's the average time a Fortune 500 company, sorry, an S&P 500 company stayed in the S&P 500 index. And it went from being like on average 60 plus years, went down to about 11 years now. I mean, there are companies that have come out of left field and killed incumbents.
Jeff Holman (43:09.762)
Mm-hmm.
Andrew Ackerman (43:18.02)
Like Netflix killing in a blockbuster or zip car didn't quite kill a traditional like, but they had to pay seven, I think it $7 billion to acquire it. And these are companies that came as far as corporate was concerned out of left field in a heartbeat. Right. Before they even knew it, all of a sudden they were on top of them. So we're definitely in a point in time where like, even if you're a large company and you can persist for a long time doing it like, okay.
Okay is getting progressively not okay.
Jeff Holman (43:49.568)
And a long time is getting progressively shorter and shorter, isn't it? Well, looking back at all of this and what you guys did to make these changes, how it's applied either in corporate or startup world, like, is there a part of it that people kind of consistently misunderstand? Like they like hear it and they're like, I got this. And you're like, no, no, no, you don't. Like there's a real way to do this. And then there's this superficial like checkbox way to do this.
Andrew Ackerman (43:52.716)
Yeah, exactly.
Andrew Ackerman (44:18.2)
Yeah. I got this is exactly how my second startup went under. but that's not as, as, as interesting a story in this case, I'll tell you where it goes wrong in, in the corporate setting. Right. So let's say whatever reason you decided to corporate, like I need to do something. I want to set up a corporate venture fund or I want to set up a, accelerator.
Jeff Holman (44:22.036)
Andrew Ackerman (44:42.256)
So you get these consultants in there and they create very paint by number versions of these things for you. Well, here's how the 20 other people do it. And here it is, we'll set this up, we'll do it. It'll be these months, these people, blah, blah, blah, blah, blah. And it turns what should be a rapid iteration, figuring out what makes sense for your particular niche and your particular strengths into a same, same, same old, same old type exercise. And if most of these groups are mediocre, then
you're going to get mediocre or worse because the more people that do it, the harder it gets, more competition there is. So even what was good before is now average and was average before is now substandard. So they end up by trying to get kind of the best practices or whatever they want to call it. They end up guaranteeing that they're going to get something which is not going to perform.
Jeff Holman (45:24.333)
Yeah.
Jeff Holman (45:36.15)
I mean, this is, I think you're describing what some people are saying is the real issue with, I mean, one of the real issues with AI, right? Like we're all using the same LLMs and getting to the same average faster, much, much faster without necessarily thinking better.
Andrew Ackerman (45:53.041)
Yeah. So you gotta like, let's I'll take writing. Like I happen to like writing. I wrote a book. I have to like writing. Um, but there are a lot of people from writing is not their strongest suit. So for them, if they want to use, uh, an AI tool and like, here's what I'm trying to say. Can you clean it up for me? And that raises them up to like, you know, a solid B plus piece of communication. That's awesome. I'll have a little bit of a sameness, a little bit of blandness, but it's better to have something that's a little kind of
Jeff Holman (45:58.678)
huh.
Andrew Ackerman (46:22.98)
bland, but does the job, then something that's like, you know, impossible to follow and poorly written. But if you want to really stand out, if you want to actually, if you want to be great at something, it's not there. Which goes back to what we were saying before, like A team, A players, right? Where do you need to be awesome? You may not need to be an awesome writer in your job. You may need to be just good enough. Like my wife is a real estate agent. She needs to write descriptions of properties.
Jeff Holman (46:31.181)
Mm-hmm.
Jeff Holman (46:40.877)
Mm-hmm.
Andrew Ackerman (46:53.07)
right in her listings. Does she need them to be, you know, like Milan Kundera level pros or does it just have to be like Hemingway simple? Right. That's fine. Hemingway simple is fine for what she does. She needs to be great at marketing herself, great at representing her clients, but just writing those descriptions good enough is good enough.
Jeff Holman (47:05.197)
Yeah.
Jeff Holman (47:16.642)
Yeah, that makes sense. Well, how has this trajectory that you've been on evolved you as a leader and maybe to be more specific, are there things that in your past roles and functions maybe gave you a little more anxiety or even fear to face that now looking back you're like,
Like those, doesn't happen anymore. I just, can deal with these things now because I've been there and seen it and done it.
Andrew Ackerman (47:46.083)
Yeah. You know, it's, you do, but if you're really challenging yourself and you're living an interesting life, there will always be the conservation of uncertainty and fear. You've just moved up a level and you're worrying and trying to learn new things. And that's great. Like I used to go back and I think about like, where was I five years ago? like, my God. Like I thought I knew stuff, man was like clueless. And that used to bother me like, I'm really embarrassed at like, know, who I was five years ago. And then it occurred to me.
Jeff Holman (47:58.99)
sure.
Andrew Ackerman (48:15.824)
The moment I wake up and ask, you know, five years ago, Andrew was, you know, it pretty spot on. was, he was not bad. That means I've learned nothing in five years. And that like scares the, you know, the bejesus out of me. So, um, there were things that were tougher, right? Like, um, knowing how to manage up, knowing how to manage my workload, knowing how to communicate. Like you learn that with time, uh, doing cold calls, meeting people, like networking in general, you know, you can get better at that over time. But then you, again,
Jeff Holman (48:24.176)
yeah.
Jeff Holman (48:37.123)
Mm-hmm.
Andrew Ackerman (48:45.296)
You go up to the next level in the game and now it's like, okay, I'm looking for these amorphous opportunities that, maybe even the people who I'm talking to don't know exists because they didn't know they wanted it until I tell them about it. Like, how do you find those people who have those latent needs and like connect to them on that level to the point where they realize, oh yeah, I never knew that existed, but now I can't live without it.
Jeff Holman (48:56.887)
Yeah.
Jeff Holman (49:07.406)
Well, that's interesting. It makes me want to flip the question because I think about a lot of our audience and people who are in the trenches right now, scared of everything and hustling as hard as they can to, know, overcome the things they're scared of. What's something in maybe generically, what's something that could be a trigger for them to indicate that, if you are now
dealing with a bigger problem or whatever, you don't actually need to continue to worry about being scared about these things because you have progressed. Does that make sense?
Andrew Ackerman (49:44.954)
Yeah. So I'm going to do the traditional VC approach of answering something that may be vaguely related to your question, but I kind of find interesting and want to say anyway.
Jeff Holman (49:55.99)
As an attorney, I fully accept that approach.
Andrew Ackerman (49:58.225)
So here, let me kind of put this out there for people who are stressed out startup founders. You only have to be great at one thing. Everything else you have to be good enough at. So I see a lot of founders that come out there and they have a product and like this feature is a little better, that feature is a little better. And they think they're going to get like, oh, I 20 features, they're all a little bit better. But the sum result of it is that it's much better. It's never going to work.
It's never gonna work. On the other hand, the startups where they do one thing that's a quantum level better than everything else and that no one else can do as well, their customers will live with a lot of mediocrity and everything else. It's like, that's awesome, I need to use it, I know it's not entirely built, I'll out-jerry-rig the rest of it. I'll download it as a CSV and I'll upload it somewhere else. I don't care, but I need that data. So understand what you're awesome about. Make sure you deliver that.
And then systematically make sure everything else is at least good enough. You can always improve that other stuff later, but you know, where you want to avoid is one of those things is not good enough and you can't sell it because my, you know, I tell them also like startups, like a chain, every link has to work. It's not like a rope, you know, a couple of strands are frayed, the rope still holds. If one link is broken, then the entire chain is, is, is useless, but like they only have to be just strong.
Jeff Holman (51:12.504)
Mm-hmm.
Andrew Ackerman (51:25.877)
If you've got that one thing that matters, you just need everything else to be strong.
Jeff Holman (51:30.412)
And you might not need a chain with a hundred links in it either for a startup, right? You might need a chain with.
Andrew Ackerman (51:35.472)
Well, that's it also. Yeah. If no one cares about, you know, that just don't build it. Yeah.
Jeff Holman (51:39.874)
build it with a dozen links instead of a hundred. Yeah, I think that's where the, I see this in the, you know, legal tech is booming right now and everything is AI based. It's like, I see these startups and I'm like, that's a startup? Like that one, like I'm dealing with, like literally I've built a fractional legal team so we can take attorneys and plug them in and cover all the issues that happen in a startup company, which is amazingly diverse number of issues as we all know.
But then I see a startup pop up and it's like, they deal with one employment law issue from one perspective and they're raising money and killing it. I'm like, well, I mean, to put it in your analogy, they've got, they must have the right emphasis and the right strength, enough strength and enough links that it's addressing a problem people are willing to pay for.
Andrew Ackerman (52:25.284)
Yeah.
Andrew Ackerman (52:29.744)
So we look at it with like these two, you know, it a company or is it a feature, right? Cause at some point if you just do that and it's like, so just that one thing, but then it stands alone, doesn't work in the workflow. Eventually it's going to get sucked in, right? Eventually someone's going to say, listen, like that's a little better at it, but this is good enough and it works with everything else. So I'm just going to do the all in one. Uh, the other danger for companies like that is market size.
Jeff Holman (52:35.053)
Mm-hmm.
Andrew Ackerman (52:59.386)
Like how big can they be? If they're not big enough, then we got to pass, even if they are solving a very targeted pain point. And that founder may make a lot of money. You just won't get VC backing usually if it's too narrow and the market size is small.
Jeff Holman (53:14.668)
Yeah, yeah. And it's, you know, we're, we're, watching all these weird dynamics play out and a lot of emphasis on a lot of things that are AI based. So, there's kind of sometimes a business model behind the business model too, I think. So it'll be interesting to see where it all lands.
Andrew Ackerman (53:28.41)
Well, in legal tech, since it's early stages, I bet you the conversation goes something like this. You know, hey, we're solving this one problem. Here's our vision slide of the other five problems that we're going to solve. And ultimately we're going to be the entire CRM or the entire, you know, ERP system for law firms everywhere. Right. But we're going to own this. We're going to expand to here. These guys are going be small. We'll buy that and we'll plug it in. They all want to be that backbone. And these are all their wedge products. That's probably how.
Jeff Holman (53:39.522)
Yep.
Jeff Holman (53:56.142)
Yep. Yep.
Andrew Ackerman (53:57.808)
because it's early in the game for this. That's probably how those dynamics play out.
Jeff Holman (54:02.446)
I'm sure it is. I'm sure you're right with that. Well, this has been fantastic and I appreciate you sharing your insights with us. What's the top takeaway that, you know, if you were looking back at other startups or maybe even, you know, younger Andrew who's entering the world in the context that we're in today, what would you say as that advice to somebody getting into this chaotic world?
Andrew Ackerman (54:29.985)
If you know, you know, I'm smiling. Cause I'm glad to give like entirely self-serving advice, sincere, but self-serving. number one thing I would say is like, listen, you gotta go buy this book. Everything you need is in this book. The entrepreneur is Odyssey. It's like everything we've talked about and more it's all in this book and it's not boring as f*ck. Sorry. so yeah, a little self-serving, but no, that's the whole point. Like I wrote this thing because.
Jeff Holman (54:36.878)
Totally fine. Yeah.
Jeff Holman (54:42.478)
you
Jeff Holman (54:55.245)
Yeah.
Andrew Ackerman (54:58.659)
These were the conversations I was having in and out, day in, day out, with all these companies I was coaching in the accelerator, with the other companies I was mentoring. And I said, you know what? Like, we're gonna write it all down. And we're not just gonna write it all down, like, here's your how-to guide. We're gonna write it like that story I told you before about SeatGig. We're gonna write it about a startup that they can identify with, in this case, a fictional startup. Take them through every step in the process.
Jeff Holman (55:24.738)
Mm-hmm.
Andrew Ackerman (55:25.613)
so they can learn it all in a memorable and hopefully entertaining way. So yeah, that's the advice I would give myself if the book existed when I was younger. Your audience is in luck because it exists now.
Jeff Holman (55:34.272)
And now it does. And where can they find that if they're looking for that book?
Andrew Ackerman (55:39.603)
I was afraid you'd never ask. So, everything's on Amazon. It's the Entrepreneur's Odyssey. I don't think there's any other book called that. If there is, it's the one by Andrew Ackerman with this very cool cover. Don't accept any substitutes. Or if you're kind of like, well, that guy was vaguely interesting. I want to hear more. You can go to my website. It's Andrew with the letter B as in boyackerman.com. A little bit more about me and shockingly also links to where you can buy them.
Jeff Holman (56:07.818)
Awesome, very cool. The only other thing I'd say is, is it Matt Damon coming out with the movie right now, The Odyssey? If you get a chance, just throw his picture on there, right? mean, that's right, that's right. Well, Andrew, thank you for coming on the show. Our audience needs a lot of these insights. They need what's in that book, I'm sure of it.
Andrew Ackerman (56:15.639)
Yeah, that was a little different.
Maybe, maybe I should get a blurb from him. It's not too late.
Jeff Holman (56:33.318)
And it's anything that we can do, you and I and the other guests that we have on here to help build some confidence, get them through some of their struggles. It's a win from our end, I think. So I really appreciate what you've shared.
Andrew Ackerman (56:43.945)
Amen. Amen. Listen, I learned things the hard way. Learn from other people's mistakes. It's so much more pleasant.
Jeff Holman (56:52.064)
Yes. And with that, thank you to all of our listeners. Thanks for joining us on the Breakout CEO Podcast again. We'll see you next week.
Jeff Holman (57:05.023)
Andrew, thank you so much.
