Hack Business Growth By Building a Product You Would Use with Jeff Epstein, Onboard.io

Hack Business Growth By Building a Product You Would Use with Jeff Epstein, Onboard.io

July 14, 2021

Jeff Epstein, the founder of Onboard.io, joins A.J. to discuss how he restarted his entrepreneurial journey after finding a problem that he personally relates to and incredible business growth he has seen since then. They discuss his lessons from his previous business, his growth hacking strategies, and he explains why business is better this time around. 

Tune in to learn different aspects of what it takes to be more intentional when starting a business including how to select a great business partner and why you should have a clear data gathering vision. 

About Jeff Epstein: 

Jeff Epstein is the founder of Onboard.io. Onboard.io is a solution that streamlines the customer onboarding process by integrating many different onboarding tools in one package. Previously, he founded Get Ambassador. 

According to him, what makes Onboard.io a more successful and enjoyable journey for him is that he relates to the problem! 

What to do before implementing growth hacking strategies?

Before implementing growth hacking strategies, you need to know if your business has a potential for growth. We have compiled some indicators to look out for:

  • Unique Value Proposition: Determine whether your business offers a unique value proposition that sets it apart from competitors. Assess whether your products, services, or business model provide a distinct advantage or solve a problem in a more innovative or efficient way compared to existing alternatives.
  • Scalability: Take into account how scalable your business model is. Check to see if you can simply grow your operations, production capacity, distribution methods, and resources to meet increased demand.
  • Customer Acquisition and Retention: Assess your ability to acquire and retain customers. Consider the cost of obtaining new customers, the likelihood of recurring business, and the opportunity for upselling to current customers when evaluating the success of your marketing and customer acquisition strategies.
  • Financial Health: Evaluate your company’s financial situation and measure your business growth. Analyze important financial indicators like profitability, gross margins, revenue growth, cash flow, and return on investment. A strong financial foundation is necessary for growth initiatives and to attracting potential investors and financing options.

To determine internal strengths and weaknesses as well as external opportunities and dangers, you can perform a SWOT (Strengths, Weaknesses, Opportunities, Threats) analysis. This research can indicate areas for development or strategic focus and offer a comprehensive view of your business’s growth opportunities.

On today’s episode: 

  • Who is Jeff Epstein? – 00:43 
  • Having a remote team and using flexible scheduling – 02:10 
  • The most intentional he has been about building a company (and what that means)- 03:38
  • Buying a business for all the wrong reasons in 2007 – 05:43
  • How having an internet business used to be more than a decade ago (an expensive learning experience) – 08:30
  • Most business partnerships don’t work out, so make sure you do this.- 10:33
  • Sharing responsibilities with a partner instead of doing everything yourself- 12:30
  • The main reason they lost customers (and how they turned that around).- 14:43
  • Knowing that there is a huge opportunity but hesitating to start a business – 17:05
  • Why starting a company that fixes a pain YOU’VE experienced is a whole other ball game – 19:26 
  • How having a clear vision of why and how you gather data makes you more effective. 21:47
  • Will Jeff be creating a channel program for Oboard.io? – 24:03 
  • Going from getting ZERO personal time to establishing a healthy work-life balance – 25:33
  • How he’s structuring his company to give himself and his team a better balance. – 28:42
  • How he was blown away by the possibility that you can actually love your job – 29:57 
  • Using bad experiences to create better businesses – 35:17 


Key Takeaways: 

  • Being intentional about building a business is all about anticipating possible challenges and figuring them out before they happen. Being intentional includes anticipating both personal and business challenges that the work may present. 
  • Most business partnerships don’t work out. When establishing a business partnership, it is important to align expectations. 
  • One of the main reasons you might be losing clients is because they may not be getting a taste of your product. 
  • Building a company that fixes a problem you know inside out is much easier than building a company where you are disconnected from the problem and don’t feel, yourself, the pain of the problem. 
  • Overworking yourself to make your business succeed can exert a heavy toll on your personal life. Part of the sustainability of a business relies on having a healthy work-life balance. Allowing for remote work and flexible hours are one way to promote a healthier work culture. 
  • Don’t fret if you’ve had unfavorable business experiences. Rather, keep iterating. Use every experience as a stepping stone to the next. 


Building a company where you’ve EXPERIENCED the problem: 

20:02 “When I’m speaking to investors and other folk and they say ‘why this time’ and then I say listen,  in the most honest way I can answer, this is actually a problem that I understand. I built a company in a problem that I didn’t really understand…this is a lot easier that I actually felt pain.”


How do you relate to the problem your company works on solving? Have you personally experienced that problem?  

Tell us in the comments, and don’t forget to say hello if you would like to share your entrepreneurship story on our podcast. 

Connect with Jeff Epstein:

Connect with A.J.Lawrence:

Follow Beyond 8 Figures:



[00:01:29] A.J. Lawrence: He has some great experiences leading up to it and the reasoning moving into it. And his new company is incredibly well thought out, fast growing SaaS play in the onboarding space for SaaS’ actually called Onboard.io. And once again, apologize ahead of time. I may be calling it Onboardio.

[00:01:50] But please everyone. Welcome Jeff Epstein to today’s episode. Jeff, thank you so much for coming on the show. I’m really excited to have you here. How are you doing today?

[00:02:00] Jeff Epstein: I’m great, A.J., thanks. I appreciate it. So this is gonna be great. I’m excited.

[00:02:04] A.J. Lawrence: Cool. Very cool. Since I’ve been telling everyone about your amazing background with a few ups and downs are along the way, could you share with us maybe why don’t we start with where you are now on your entrepreneurial journey?

[00:02:16] Jeff Epstein: I’m at I feel a really fun part of the journey now, because I think now is the most intentional I’ve been in terms of building a company around what I want to do every day and including the people that I want to do things with. So right now I just recently founded a company called Onboard. It’s onboard.io and it’s software for customer onboarding, which was a big problem that I experienced with my last company Ambassador. It was a problem that myself and my co-founder, Will Stevenson, spent hours and hours and literally years thinking about. Will has spent almost a decade or more thinking about it.

[00:02:51] And so we really decided there’s nothing, there’s no software that does this well, helps companies do this well. So for us we got to build something that we knew scratch niche, and we knew would have, I think, a big impact in the market. But what’s nice about that is we built an intentionally, fully distributed company. Will and I aren’t in the same city. Our team is spread out across the globe. We’ve all worked together before. So just doing a lot of things differently and hopefully allow for some more flexibility, which is I know, really on trend right now, especially post COVID or near, during COVID. And things that we even saw in my last company where we had multiple cultures of people that were 9-5, 9-6, and then we had people that wanted something different.

[00:03:31] It was hard to have, I thought it was hard to have both. So I’m glad we’re starting with very flexible scheduling and I’m trying to do it myself as well.

[00:03:38] A.J. Lawrence: When you said really building around intentional, what is it being intentional in building a company mean to you?

[00:03:45] Jeff Epstein: That’s a good question. I think as an entrepreneur, one of the skills that we have as entrepreneurs, at some point in the future you realize that most people don’t have the skill is this level of comfort with just figuring things out on the fly or not necessarily being prepared, but being okay with that and being able to roll with the extreme highs and lows. That being said, those are still happening, but we try to plan for the things that we knew we needed to plan for. So like the early employees, the initial sort of vision and mission of the organization.

[00:04:17] These are things in my previous businesses that you horse correct and you figure them out after you have problems. So at this time it was like, okay, let’s figure them out first. Let’s use them as a way to bring people, no pun intended to bring people onto our company. Now let’s set a vision in something that we wanna live by and how we wanna operate as an organization. So that was much more intentionally thought through.

[00:04:37] And even when I first discussed doing this with Will, which was during COVID, we said, well, if we’re gonna do this, let’s do it this way. And it means let’s not only live to work. Right. Like we know people wanna have the flexibility. Will has three kids, he has an active lifestyle. I run into a situation where I think Craig was burned out and I overworked myself so we said, we have to do our job to not work 100 hours a week either.

[00:05:02] We want to do what needs to be done and we’re willing to put in the effort and the time, and I think that’s not gonna change, but we have to give ourselves personally enough room to be good parents for Will or, but he is a great parent, but like to be good spouses and all the things and be good to our son.

[00:05:16] And so that was a little bit more different. And from that perspective was a lot more intentional than Ambassador (where) I was living in my parents’ basement and it was like, Hey, we gotta scratch and claw and do whatever we can to get enough money. We weren’t putting my wife’s paycheck back into pay developers, so it was very different. And fortunately, I can think about things a lot differently now.

[00:05:33] A.J. Lawrence: That is a cool experience to be able to get through the other side of really a great company, but then be able to understand what it means for you personally and then for what you’re trying to do as a company to achieve even better.

[00:05:46] There’s so much fun stuff I wanna play. There’s a big thing right now that a lot of entrepreneurs have been looking at. It’s gotten hot for a couple years but definitely in the past year, it’s acquisition entrepreneurship. And you seem to have the reverse experience that everyone touts, especially everyone with a course in the gazillion books, but yet you still continued on as an entrepreneur.

[00:06:06] We’re gonna jump back a little bit to a little bit earlier in your entrepreneurial journey and tell us what, if I’m correct it was 2007, why did you think about acquiring a company back then?

[00:06:17] Jeff Epstein: Sure. And I have an interesting journey. So I’ve always been entrepreneurial and I’ve always been mystified. And always, I think looking back, always wanted to own a business.

[00:06:27] My family’s been entrepreneurs both sides, both my grandparents. And I was always fascinated by having companies and businesses. And originally my first company was in law school. So I went to law, graduated undergrad in 2004. She started a company, a very early internet company that wasn’t successful in the year 2000.

[00:06:45] But after I graduated in 2004, I created an affiliate company based on online poker cause I was very obsessed with online poker. It was very popular and it was massive and we just happened to be at the right place, at the right time. I had a bunch of friends who went to school with me that were like pros and doing extremely well in tournaments. So we ended up seeing really the power of social, which sounds so weird to say now, but like back then it was only AOL and Facebook was just starting. And so being able to connect with friends of friends and seeing like this like massive world, it like changed everything for me.

[00:07:18] So I did that. We did well, I mean enough to pay off my law school loans, which was great cause I was in law school in Chicago. It was very expensive. I had to borrow all the money to do that. So I was able to pay off my loans and I had a clean slate, but it was also what I was gonna do with my life? I didn’t want to be a lawyer.

[00:07:32] So in 2007, I’ve had a little bit of money and I moved back home to Michigan, to live with my parents and to figure out like, what am I gonna do now? I don’t wanna practice law. I don’t have this burden of this six figure loan anymore and I have a little bit of money to do something, but I don’t have, I have a six months or a year’s worth of like being able to figure it out.

[00:07:50] And so what happened was a friend of mine, who was an investor in the valley and also moved back to Michigan for family reasons, he said, I found a company for you. It’s a software company. It’s SEO software and you can get it for a steal because it’s run by an agency guy and he doesn’t want to do it anymore.

[00:08:08] And they happened to meet each other in some scenario. And my friend was like, this is perfect for you. I knew nothing about SEO. I knew nothing about software. It was a good deal in hindsight and that was how I got into it. But I got into it for all the wrong reasons, truly. It was a good deal and I wasn’t passionate about it, but it seemed like such a great opportunity.

[00:08:29] A.J. Lawrence: I like so much that from the seed of failure, difficulty or reversal, you did get a success because that did lead to Ambassador because of what you were looking at the time with it.

[00:08:41] Jeff Epstein: It did. And it was an expensive but very valuable learning because at the time too, and I have air quotes and I know we’re not seeing these, but at the time it was there was no such thing as a "startup". It was an internet business, which was weird back then. Like, it wasn’t a cool thing like it is now. It was actually weird.

[00:09:00] It was like abnormal that you had a job on the internet, that you had an internet company. And I knew nothing about, so I didn’t know anyone who had an internet business. I didn’t know anything about software development. So the company that built the technology was in the Ukraine and they were like holding me hostage. They basically wanted me to pay them three times as much money when they found out I bought it. So it was like right away, there were massive problems that I did no diligence on whatsoever.

[00:09:25] And I didn’t know to even think to do those things, which is so dumb in hindsight, but these are things that you learn. And of course when we built ambassador and subsequently other companies, I made sure I need someone to vet out the technology, right? A company, even with amazing revenue, if the software breaks and you don’t have anyone reliable to fix it, it’s not worth anything.

[00:09:44] Those are little things, that it was like a small thing would happen or the servers would go down and I didn’t have a trusted person to fix those, you’re just giving refunds. Right. You’re just losing money or it’s going. So those were the things that I didn’t think through well enough and truly learned as I did, and those that I think allowed me to survive ambassador and not let it ruin the company, which it did with the other one. The technology was so specific. I ended up making a pretty good trade cause the person I worked with, we swapped equity between Ambassador and this other company that I bought.

[00:10:14] We made a trade, which worked out very well in my favor, but at one point the person was working on both for me. And we realized that it was just too much work and he ended up basically taking the other one and I took Ambassador. With what I knew, I was able to manage the technology team and kept it afloat, but it was an expensive learning, but definitely valuable down the road, actually.

[00:10:33] A.J. Lawrence: That is an interesting thing. That kind of progress of that kind of thought process with the partner. Now I’m hearing more than a few people getting, was he working on it? Was he a partner equity? What did that look like when you guys, before you decided to swap?

[00:10:56] Jeff Epstein: I originally inherited the outsource team and then I went to look for my own outsource team. And because I was desperate and didn’t have enough money, I offered a big slug of equity plus paying them. And so he was essentially a partner of mine. But what I realized, which something that again they teach you in law school and I should have known better is, most partnerships don’t work out. And more so, it’s important to align everyone’s expectations.

[00:11:23] And so I was partnering with someone who also had another full-time job and this was the only thing I had going in my life. And so that was not a reasonable thing to expect someone to put in the same amount of effort as I was. And so, you know, we ended up doing up sort of buyout/trade so to speak. But yes, ultimately he was a partner, very early partner of Ambassador who sort of did the very first iteration, which had been redone multiple times over.

[00:11:49] He was originally going to work on both and my plan in my head was, oh, I’m gonna have all these different internet businesses. Cause I didn’t think about like growing a team. It was more of I’m gonna own and build these things. I have so many ideas. And I actually also did another one that was very much like Thumbtack before you’d heard of Thumbtack, but I couldn’t get it off the ground. So I actually, I had what I called myself of being a startup collector, which I think is a dangerous position ideas.

[00:12:14] A.J. Lawrence: Yeah, I love that. That’s more honest than I think a lot of us get with the bright, shiny object syndrome and calling collection. Yeah I mean, I call it portfolio, but you’re right. It’s probably being a collector, if you’re being nice. I like that. I might have to use that.

[00:12:31] But what’s really interesting is we started off the conversation talking about you and your current partner and the work that you’re doing together. When did your current partner come into the situation?

[00:12:42] Jeff Epstein: So I met Will at Ambassador. Will joined ambassador in 2015 and we met maybe a little bit before 2015. And it was really at the point where we decided Ambassador was going to be a real company. And he joined originally as a consultant actually. Because he was from Ohio, he lives in Cincinnati, and so him and his prior partner Zach who played huge roles at Ambassador eventually and were part of the leadership team and both had become really good friends of mine, they originally were going to be contractors for us because we didn’t really know how to take that next step at Ambassador and go from Jeff doing everything to having specialized folks who knew these things, knew the functions way better than I.

[00:13:23] Up until that point, I had basically been carrying everything non-technical on my back. We had some great technical folks that were managing sort of the product, but the sales, success, marketing, I was doing all that. And not particularly amazingly either, but I was certainly putting in the effort. And so Will and Zach came in and then they brought the sales and then the success expertise that we’ve been lacking. And like we 3x’ed the business in the next 12 months.

[00:13:48] It was a trajectory change for Ambassador and we’d then raised money and then we went on the path towards 10 million and eventually the acquisition. So that was the big change, and that’s where I met Will and we worked together pretty closely and like I said, have become close friends as well.

[00:14:03] A.J. Lawrence: Oh cool and it does sound like you’ve learned your lesson in building this partnership to make it such an important part of onboard.io. Actually I would love to talk a little bit. We talked about the importance of why you built onboard.io. Sorry, you know what, we were chatting about this before the show I’ve done this to both your brands. I call ’em by their domain names not the actual brand names. So yes, I was joking outta the show that I call ambassador get ambassador because that’s the domain and onboard.io. So IO, I just, you know, it’s a cooler name now it’s a great name onboard.

[00:14:42] As someone who’s had a lot of difficulties for clients over the years, and then also for my own things on onboarding, maybe we can talk about the pain points from your own experience. How did you kind of go from this is my pain points to wait this is starting to become a real business and maybe walk us through and share a little bit about how this helps folks like us who are listening here.

[00:15:07] Jeff Epstein: Sure. Challenge that we had at Ambassador, and I think this challenge resonates across software companies, but specifically SaaS. Because the best part about SaaS and Software as a Service is that your customer is re-upping, whether it’s monthly or annually, and that’s incredibly powerful from a revenue perspective and a business perspective. But it also to me raises the bar on customer service and how you treat those customers.

[00:15:34] And I guess the inverse of that is what the lifeblood of SaaS companies is retention rate, right? So you need to keep your customers. And the worst thing that can happen is what’s called churn, which is when they leave the company. And so for every SaaS business, we measure churn, like it was my number one KPI.

[00:15:52] And like, how do we get our churn rate? The number of people leaving, how do we get it down until we get less people leaving of course. And so we tried and we experimented and tried so many things. Eventually at Ambassador, we ended up selling primarily to enterprise companies. So they were average contract was $25,000 a year, many were in the hundred thousand dollars plus. And we realized that, and what’s so great about affiliate marketing, or we called it referral marketing but it was truly the same as affiliate marketing, is we were tracking and managing it.

[00:16:22] We know the concept, conceptually it works. It’s highly efficient to pay someone a dollar every time you get $5 in revenue. We know that concept. The way that we lost customers, most of the time was if they never actually used us, because it was too hard to configure for whatever reason. It shouldn’t be hard, but in big companies, a lot of people have a lot of objectives and incentives to do things and we couldn’t make them do what we wanted, right?

[00:16:46] And so ultimately we realized, we need to figure out how do we get them to use our product? If they use it, we know that they’ll stay with us, either their X times more likely to stay with us. If they don’t end up using it, of course, we’re going to churn. We just don’t know when. And so Will who founded Onboard and really was his idea, so to speak.

[00:17:05] Because he said onboarding is a mess everywhere. And Will came up with a solution. He used a patchwork of several different technologies. It was basecamp and monday.com and Google sheets and email, and we had surveys. And we would ask our customers, on a scale of 1 to 10, how does this rank across any other software technologies you’ve integrated?

[00:17:26] We almost exclusively got 9s and 10s. I think we only got an 8 one time. Like literally out of hundreds of people, we got all 9s and 10s, which is great, but it was really the process. Will created a process with piecemeal solutions that was better than what anyone else was doing.

[00:17:41] And we said there needs to be a way to put this all in one place. And so we knew there was a need in 2018. We didn’t do anything about it for a few years later. And after we sold in 2018 Will had become a good friend. By that point we talked very regularly, maybe every week for sure, but maybe even every other day, every couple days.

[00:18:00] And he was doing consulting for companies and he was helping them with their onboarding process. And he’d say, man, there’s still nothing out there to do this. And so that was when COVID hit and my plans of traveling the world and doing all these fun things were on hold, you know, I said, okay, maybe it’s time we get the band back together and do this.

[00:18:17] So that was really the impetus was. Will was saying, Hey, there’s still nothing out there. And I was the one who was mostly hesitant saying, I don’t know if I want to do another company. Like I’m burned out still. It’s nice not doing anything for a while, but with COVID hit and I was stuck in a small apartment. It was like, okay, now let’s do it. And so that’s what we did.

[00:18:36] A.J. Lawrence: I love it. Because with my marketing background sort of growth focus, I’ve always lived by the customer lifetime value equation. It can be like three little variables or I’ve seen graduate level work in some books where it’s 18 pages long variables.

[00:18:53] When you talk about it, but I always like to say, it’s let’s look at different aspects of that journey, mark up and isolate it and look at it. And for SaaS, especially the onboarding, the things of how quickly after they purchase that they take an action? How quickly between the first person and getting someone else on the team, adding a team member, scheduling their behavior action, getting a result from, getting a feedback loop occurring. All those things are getting pretty industry standard of this. But the problem is, this is why I think onboard.io is such a cool thing, because it has I’ve seen some attempts at onboarding, but not very smooth. You’re coming in from the experience of having been on the journey where I think some of the others have been technical solutions that kind of just jobbed on to some pieces.

[00:19:45] So I like that you really do focus on increasing the value in that part of the equation of like, how do we get a better experience to then set them up for better lifetime value.

[00:19:57] Jeff Epstein: Yeah. No, thanks. It’s funny. I have said when I’m speaking with investors and other folks and it’s when they say why this time. And I say, listen, in the most honest way I can answer this is, this is actually a problem that I understand.

[00:20:12] I built a company in a problem that I didn’t really understand before. This is a lot easier that I actually felt the pain. I understood affiliate marketing conceptually and thought it was a good idea. I knew very little about what was out there in the world when we started. And some of it was locked and a lot of it was doing things wrong and changing and figuring it out. Whereas this time it’s, okay, we know we can be a little bit more prescriptive because we know what it takes to do this well. And so it’s a different challenge from that perspective, but it’s fun to have the confidence of saying, we know this will work if companies adopt this methodology, so to speak.

[00:20:43] Whereas before, I knew the idea of affiliate marketing worked, but I didn’t know if ambassador actually made that better. I mean, at the end, I did. Through enough customers, I did. But when I started, it was just an idea and frankly, I didn’t know how to do enough research to realize that there were other companies doing this and maybe it wasn’t even a good idea to start. I didn’t know enough about technology.

[00:21:06] A.J. Lawrence: It’s funny cuz if I think about it, I didn’t realize how early Ambassador had started. I knew a little bit, I guess, around 11, 12 about your existence, but it really wasn’t around 15, after I sold my agency that I was on my own, that I started hearing in the wild from folks who were using Ambassador and Design Pickle.

[00:21:27] I know which I call it founded design pickle. God, that’s horrible. I do that. I always forget people’s but he had talked about using you guys and stuff like that. So it was like, oh, that’s interesting. And it sounds like that was about the time you guys also took it to another level with onboard.io, I’m like forcing myself not to just run through it. But one of the things I find really interesting when I was going through it cuz I like looking at data and I like thinking about what can we use from the process to learn ongoing. Not just get a better result now, but use it to go. You’re in a position, especially in such an important part of that customer journey, the customer lifetime value, however you like to discuss it, to really gather some great aggregate data.

[00:22:13] And since this is the day of data models and machine learning and stuff like that, are you guys looking at how to use this as you go forward ?The data and your data results from this process?

[00:22:24] Jeff Epstein: Yeah. And it’s one of the things that we’re doing right from the get go. We’re not displaying the data to the clients completely yet. We’re basically logging every interaction that takes place and for the reason that you mentioned. So we wanna be able to point out to customers that, oh, when the due dates change, they’re X percent likely more likely to not ever get completed. Or when the task we are tracking in our app, all the activity that’s happening and creating the sort of master log that will be filterable and sortable, and with the idea that we can then create some models and train them to look ideally across verticals of our customers and cohorts.

[00:23:06] Again, broadly and say, and provide insights. And again, more prescriptive insights for them saying, an example would be, you’re probably going to need to give your client more time to get this accomplished or days to launch or all of the KPIs.

[00:23:19] And again, the KPI and even I think the category of onboarding technology is still very early in its life cycle. But we wanna be one of the players that you say, oh yeah, onboard knows what they’re doing and they’ve been doing this for a long time before tools exist. We want us prescribed to this methodology. We wanna build our KPIs around the things that they’re measuring. So we’re just building that out now, but we think there’s a big, there’s a lot of room there.

[00:23:44] A.J. Lawrence: That would be something I would love as I’m building my team InsightLabs around how to maximize that customer lifetime value equation. What pieces need to be worked on at what point that kind of finding those people who are focused on increasing the data in that piece would be great to talk to you down the road. Are you looking to create a channel partnership channel program?

[00:24:09] Jeff Epstein: Yeah, we don’t have one yet, but we are definitely going to do it. I mean, we know the value firsthand. It’s, in some ways especially like in the last whatever six months with all these specs, this is off subject, but every company I see all these announcements in IPOs and man, we had so many customers at Ambassador that were multibillion dollar companies that we played a large role.

[00:24:31] I mean, obviously it wasn’t the primary reason why they were successful, but man, I mean, there must be 20 or 30 IPOs in the past few months. And so they were an early customer and just hearing the names I’m like, where have I heard that before? It’s like just random names.

[00:24:44] A.J. Lawrence: It’s funny. I was looking for someone and they were like, oh, so who’s using it. So I did just a site.getambassador.com and took out some variables. So I was getting lists of login pages and I was amazed at just the range of businesses. And there was one I fell in love with, and I almost bought, but I moved to Spain so I never did the sort of the Peloton of rowers. And I was just like, that is such a cool- and that they were on your platform.

[00:25:12] Sorry, I’m just taking it off there, but that is so cool that you are looking at that type of thing because yeah, I do think having that process, having that way, that’s something where you can build out the resellers, the people who follow your processes and bring into their efforts onboard. I think that is really cool.

[00:25:31] Just to jump a little bit, just cuz one of the things we’re joking about is the things that you’ve gone through. And you had mentioned, you didn’t really wanna start a company, you’re in this idea you were gonna travel around world, Ambassador had been a great exit yet the situation, the time came, which was great about your journey, but how do you keep that balance of you versus the business? We had chatted a little bit earlier before the call. Can you share a little bit about your effort to have Jeff be something and not be like I used to call myself. It was like my local company and me, it was like, wait a second. What? I need to work on that. So how do you make sure that you stay Jeff?

[00:26:12] Jeff Epstein: That’s really tough. What’s so tough, and I think this happens with a lot of entrepreneurs, that is you become almost one. Your identity becomes the company because I think most entrepreneurs, they are willing to do things that most say average people aren’t willing to do to try to be successful. And it requires that. And so for me, what that meant was for almost 10 years, I spent almost all my time primarily thinking about the business and it wasn’t always intentionally, but I think that’s just what naturally what happens.

[00:26:45] And what that means is when I got married, we lived in my parents’ basement for a period of time. It means we had a very short honeymoon. It means we didn’t have kids. Partially, that was one of the reasons, right. We took a lot of sacrifices in terms of, we didn’t do a lot of vacations or I worked during the vacations. And these are not things that I necessarily think you have to do, but given what I thought was necessary and how I was wired, that’s what I did.

[00:27:09] And the result of that, aside from ideally a company being successful, was I probably gained 40 or 50 pounds over those 10 years. I was probably not as healthy and physically and mentally, and probably average 4 or 5 hours of sleep per day, to be completely honest, or maybe even less potentially. Thankfully, I can work off almost no sleep for a period of several days and then on the weekend I might sleep like 12 hours, but that’s not super healthy, right.

[00:27:35] So once we sold, my goal was, I literally was gonna go to a camp or like a, I forgot even I was going to go to this place, like in Utah or something go for a month. And just literally do all this wellness and stuff.

[00:27:46] I ended up not doing it, but I instead physically said, okay, now it’s time to lose weight, take care of yourself. Like you optimize for yourself instead of all different business. And having done that, you feel a lot better and you feel like more energized and you feel better about and probably your relationships are a lot better and all those things.

[00:28:02] So knowing that I was capable of fixing some of the things that I ignored or definitely didn’t do well in terms of personal health and relationships over the first, the 10-year journey, I knew that I had to, if I were going to do another company and start another business, I needed to have a better balance and have some boundaries.

[00:28:21] And it’s still hard. Like I still wake up in the middle of the night and check my email. Like I still had an online chat at 11:30 on Friday night because a customer from Australia was asking us a question and I got excited and I wanted to help them. But for the most part, my goal is I try to work out every day.

[00:28:36] The company itself, our mission is and sort of our principles aren’t about outworking everybody. I mean, I think outworking people is important, but it’s not the expense of your family or yourself. And trusting people to make the right decisions. And so I think we’re trying to frame conceptually how we operate.

[00:28:53] It’s remote first, it’s fully distributed. We’re trusting people with their time and basing them on resolve. We’re all like adults now. We’re trying to hire folks that I’ve worked with before so we’re not like micromanaging. And so all those things are a little bit different in terms of how do I make the journey much more of the way that I wanna work personally, selfishly, but also I think hopefully that resonates with the people that we bring on.

[00:29:14] And I think it changes a little bit of what type of person we work with as someone who is mature enough to do things and not take advantage of the lack of management, or someone who is so inexperienced that they need someone to tell them how to work.

[00:29:29] So we’ll see. I mean, we’re not big enough yet. It’s five of us and hopefully we don’t have to change that too much, but we’ll certainly, I’m sure face some challenges as, as we grow.

[00:29:37] A.J. Lawrence: As you grow, you know, just because I really do think onboard.io really looks interesting and I know it hits a pain for a lot of my clients over the years. And obviously you had with getambassador many more than me as an individual or, you know, with an agency. I could see this really being very interesting. So I’m looking forward to seeing it as you move forward.

[00:29:58] You talked about your marriage. You’re trying to create the Morris life. Do you think much about the legacy you’re building? And I know legacy gets weird sometimes for folks, but as you know, I say here, look for 99.9 of us it’s not about buildings and names and stuff like that. It’s about what people will remember you. Do you put much effort or much thought even into what that’s gonna look like few years, X years, whatever years, hopefully quite a long time down the road for you.

[00:30:31] Jeff Epstein: Yeah, it’s a great question. And to be honest, I think at first I used to spend more time thinking about it than maybe than I do now. But I think the reason was I, coming from Detroit and this may or may not resonate with everybody, but Detroit is like a blue collar town. It’s also though a uniquely union town. And which means is there’s always this weird, there’s an adversarial I think underpinning to work where you’re not expected to really like the place you work.

[00:31:11] It’s like for the most part growing up just across friends and industries and all different, there was always like a resentment between sort of owners and employees and from both sides, right. It was like this weird thing. And when I learned about startups and when I learned about people that love their job, it blew me away.

[00:31:28] Because like I was going, potentially going into law where it sounded miserable, but it was like, that’s just the way the world is. It is miserable. You just show up for eight hours, you go home and then you open up a beer and watch the game. Right. And so for me, it was so mind blowing to think that, wow, I can like enjoy what I’m doing. I can be passionate about this technology or this thing. And I can enjoy my co-owners and employees. And so it was such a change from what I expected out of my life, that I was like, I need to figure out how to do this in Michigan, in Detroit.

[00:31:59] And that was like my original goal was like. I want to build an incubator and all these things. And what I realized was no one knew what I was talking about back then. And so I would’ve talked to all these entrepreneurs and they’re all like, yeah, we need to do this. And then I realized, you know what, the only way to actually make a change in this area, which again now with information and social, it doesn’t need to be so regional.

[00:32:20] I think a kid in Detroit knows about this stuff because he can see things across all the social media, but at the time this wasn’t prevalent. And I thought, well, the only way I can really do this is if I can build a successful company, then I can teach all the employees to do this too. We used to say, we want this to be like the smartest place you ever work at.

[00:32:37] We might not make the most money here. You may not like, we may not be the best for everything, but we want our people on our team to go out and do amazing things after they’re done here and learn the tools that we’re willing to invest and provide, and mentor you with to create these amazing outcomes, like in the future.

[00:32:53] And so from that perspective, it’s really cool to see like ambassador and all the folks, they’re like the ambassador mafia, so to speak, right? All the people that worked at ambassador that have started new companies and raised, I mean, there’s much more money raised from people that worked at ambassador than the amount of money we raised at ambassador, which was only $3 million.

[00:33:10] So it’s cool to see that. It’s really fun to see people end up getting really great jobs at various companies. And so that was how I picture like a legacy. And I know it was a long answer, but less so it’s weird to say, but I actually don’t really like talking about myself or being like the center of attention. So it’s much less about a building or a statue or something like that. I’d rather just have people say, yeah, like I really learned a lot or that was a really great experience for me more so than let’s throw a party for Jeff.

[00:33:43] A.J. Lawrence: No, I like that. I agree. There’s something cool about when you see ex employees go on and create their own companies. It is just a very cool thing to see happen because it’s like, wow. I maybe was probably a little, teeny bit, but probably not too much of my own involvement, but I at least hired interestingly and entrepreneurial people, so that was such a cool experience. So that’s gonna be interesting to see what that wave of people, the onboard mafia looks like down the road.

[00:34:16] Jeff Epstein: Exactly.

[00:34:17] A.J. Lawrence: Jeff, we’re gonna have a link to your background to onboard.io. But since I keep saying it, everyone onboard.io. So if you want to go check out their onboarding experience, please go check it out. I just really appreciate that you came on the show today. Thank you very much.

[00:34:34] Jeff Epstein: Yeah, thanks for having me, A.J.. It was great. A lot of fun to chat and a good walk down memory lane just to think about the journey. Sometimes it feels like it’s been a few weeks and sometimes it feels like it’s been my whole life. So it’s fun to talk with you and I appreciate you bringing it up and taking the time.

[00:34:49] A.J. Lawrence: Yeah. And you definitely have come from just the different steps and the way you’ve described the different things. It’s yeah. You’ve done these things that it probably have felt like you’re constantly in it, but it’s wow that skill level there very impressive, but where you are now, that ongoing progression has been very cool to listen. So thank you. You have a wonderful day.

[00:35:09] Jeff Epstein: Thanks. You too.

[00:35:10] A.J. Lawrence: Hi everyone. I hope you really enjoyed today’s episode with Jeff because there was a lot of great stuff and his journey now to onboard.io, I will not onboardio it, is really very cool. The steps he’s taken, the amazing exit he was able to get out of ambassador, get out of I didn’t say, get ambassador.

[00:35:31] They’re all about the steps and the iterations of his earlier efforts as an entrepreneur and his continuation in this process. Some of the things definitely to look and think is you go and listen to the go back and possibly listen to the episode again, is look at sort of the types of partners you’re working with and the reasoning why and how you’re coming to it.

[00:35:55] He was able to take the bad experiences he had early on, and we all have partnerships that don’t end up being what we hope could be in other aspects of our lives, whatever. But he didn’t just limit himself to partnerships are in, he went and actually used his experience of not having a good partnership. Got out of it quite well as the foundation of ambassador, but then went on and built a new partnership because of his awareness with someone who came and helped him really take ambassador to that next level.

[00:36:27] And I’m really excited to see what they do with onboard.io, because it really does seem like they’ve hit that niche of onboarding for that space. Matter of fact, I know my team and I are gonna be looking at it for our customers in sort of our growth plans with insight labs.

[00:36:46] Yeah, we’ll have some links down below for Jeff. Obviously we’ll have links for onboard.io and checking it out, but we really do hope to talk more about this because it is a very interesting software. We’ve had a couple of software plays that we think are worthwhile for you as a business person to think about, as an entrepreneur to think about for your business.

[00:37:10] And if you’re in the SaaS play, this onboard could be a very interesting play. Also, I do think taking away his building up of intention using the previous experiences, using his understanding of where he was in his journey, thinking about it and taking each of the steps, looking at how we are and realizing that we can build businesses that are more intentional towards our own goals, not just chasing after things.

[00:37:38] So once again, I hope you really did enjoy and learn a lot from this podcast. Today’s episode really helped me think about a lot of what I’m trying to do with insight labs and with this podcast. So I hope this was helpful for you. Once again, we’ll have links for Jeff down below for onboard.io and as always, we’ll have our own links, check out our social media and feel free to always give us a shout out. Let us know what you’re thinking about this, what you would like us to do, and, any other advice, please? I really do appreciate all the comments people send our way. All right. Have a wonderful day. Can’t wait to talk to you again soon. Goodbye.

[00:38:24] This episode of Beyond 8 Figures is over, but your journey as an entrepreneur continues. So if we can help you with anything, please just let us know. And if you liked this episode, please share it with someone who might learn from it. Until next time, keep growing and find the joy in your journey. This is A.J., and I’ll be talking to you soon. Bye bye.

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