Taylor Trusty, Entrepreneur, Speaker, and Strategist

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Taylor Trusty, Entrepreneur, Speaker, and Strategist

Taylor Trusty has founded three companies: HobbyEdge Sports, StarkNine, and Blackstone Media -- a digital marketing agency that helps brands like Toyota Forklifts, Sonoma-Cutrer, and Mercer tell their stories and get more business through the web. In 2018 he sold Blackstone to Boston-based ADK Group. 

He has spoken to over one hundred groups on entrepreneurship, digital marketing, usability, and company culture, including the American Advertising Federation, Entrepreneurs' Organization, Vistage, Kentucky Press Association, The Combine, D2 Cincinnati, Code PaLOUsa, and more. 

Taylor is a consultant, podcast-enthusiast, board member of Entrepreneurs' Organization NYC, and a regular at Comedy Cellar.

Twitter: @ttrusty
Instagram: @taylortrusty


[00:00:01] You're listening to Scaling Up Services where we speak with entrepreneurs authors business experts and thought leaders to give you the knowledge and insights you need to scale your service based business faster and easier. And now here is your host Business Coach Bruce Eckfeldt.

[00:00:23]Welcome everyone this is Scaling Up Services. I’m Bruce Eckfeldt, I'm your host and our guest today is Taylor Trusty and Taylor is an entrepreneur. He's also a fellow member of the Entrepreneurs Organization here in New York City. And I wanted to have him on. He's got a lot of experience as a founder as a CEO and also having gone through an exit. So I wanted to get his insights on service based companies and the experience he's had with that. Taylor welcome to the program.

[00:00:45] Thanks for having me. So why don't we start with a little bit of background how I guess how did you become an entrepreneur. How did how did your business start.

[00:00:53] What were you doing before you started the business and let's kind of let's get the origination story here and kind of hear how things things began. Sure.

[00:01:01] So I was obsessed with computers from a young age. They started programming when I was 13 and I started building Web sites. I was 13 14. I was really big in the computer games and played counterstrike and I failed my freshman year of high school.

[00:01:15] I played too much counterstrike. And I so in the gaming world you create they're kind of these organizing groups of players you get on clans. And I ran a clan called social destruction of the government's pretty.

[00:01:28] Aggressive pretty anarchy and I get this guy. Yes.

[00:01:32] Would you say three for a strong move I think for us by 14. And so I built this Web site for us. And I didn't have any money right. So I befriended this guy who on this hosting hosting company and he gave me a lot of free advice and free hosting for the Web site. So built the site is very proud of it ended up getting my first job at a web design company when I was 15. And then that led to I was a programmer and then that led to me getting a job at Hewlett-Packard. So I was a TSR a territory sales rep. I went into retail stores Comp USA Circuit City Best Buy a lot of them aren't around anymore. I went in there and sold sold computers printers scanners and so that was really fun. I was the youngest so so they had never heard anyone under 18 and I was 16. Wow. So as young as eight hired at that point and then my last job was my senior year of high school which is 18 and I worked as a programmer and also head of customer service for this e-commerce company we sold sports trading cards online and primarily on eBay. And so three of us there you know we got kind of arrogant and we thought maybe we run this place we should to start our own company. And I had always wanted to start a company. I had never wanted to go to college. I wanted to drop out of high school. So I failed I guess.

[00:02:50] You fail to fail I fail to fail.

[00:02:52] Exactly. And so so the three of us decided hey when we leave and start our own company. So I was 19.

[00:02:58] They were 10 years older than me. So they were twenty nine and I dropped out. I did actually go to a couple of semesters at the University of Louisville. This is on mobile Kentucky. So we started this company called Hobby edge sports. We sold sports collectibles instead of trading cards. We primarily on eBay 85 percent of our revenue was eBay built that up that's about half a million dollars in revenue in the first year which I that was pretty good. You know rented a warehouse and we had a small office. Louisville is a great place to do e-commerce in particular because World port which is U.P.S. is main hub is based in Mobile. That's right. So you can you can ship all wait till 10:00 p.m. as if it went out the same day. And that's one of the only places in the country where you can do that. It was a great learning experience. I ultimately kind of had a falling out with my partners and so they bought me out. I left the business and then I was back to kind of freelance programming and doing work and then a friend of mine. I'd done some contract work for asked if I'd start this company with him over lunch and I was like Sure. So we started what became Blackstone media that was in 2006. I bought him out in 2010. And so I was the only owner between 2010 and 2018 when we sold to an agency in Boston. And then during that time I also started a software company I funded most of it and they raised a small round from a venture capital firm and ultimately blew through all the money and shut it down. So the three companies I guess in total.

[00:04:27] Yeah. And you know different different setups different outcomes different experiences I'm sure.

[00:04:32] So you know you mentioned something in the beginning which I just wanted to kind of highlight just maybe almost as humor that you know our entrepreneurs are always I always find entrepreneurs want to find people just like them to come work for them. You know that they are like oh I want to I want to find other people like me who feel ownership in the company of stuff. And the thing I always tell them is look as an entrepreneur what did you do. Like you work for someone and then you got tired and left and started your own company. The last thing you want actually is people just like you working for you. That's typically not a great strategy because I just see you end up you end up getting know entrepreneurs are always there looking for new opportunities or looking to kind of create newness they're really not in many respects not looking to kind of follow the leader in that in those cases so yeah you clearly are cut from the entrepreneurial cloth. A lot of credit. Yeah. So you know we've spoken about some of your history before so I had a couple of questions or things that I think would be really helpful for our audience.

[00:05:29] You know what I think it's the fact that you've had such a good run with a service based company I think is really interesting because I think that you know service companies are you know have their own kind of models their own kind of challenges and you I think have gone through a lot of them. You know I know at one point earlier in the company you had kind of an experience of you know trying to figure out who you were really servicing what was you're really kind of offering Who is your core customer you know because I think a lot of companies start with just kind of chasing money. They did what. Basically anyone who willing to hire them for anything and pay them they're willing to try to do it. And you know it's good to be scrappy but I think at some point it leads to a lot of kind of confusion and a lot of difficulty in terms of operations and staffing and things like that. Tell me a little bit about how that played out for you and what what was a moment or what was the time when that kind of changed or where you saw kind of a different approach to that.

[00:06:23] I think that there are a couple of parts. So when I ended up buying my business partner out in 2010 the staff that we had we had six employees and six or seven. And you know that the team needed to be changed a bit. So we turned over a lot of those employees and we moved from kind of that approach that you're talking about. If you came to us and you said hey you know I want to pay you a thousand dollars a month to do SEO or Search Engine Optimization we'd find a way to make it work right. That's okay. Because we could do this and this and we were doing it for a hundred thousand year in revenue then and wasn't seriously profitable. We were just kind of paying our bills. And I didn't want to be as scrappy anymore. So we started building more expensive websites. The aim was to build 15 20 25000 Web sites and to do that in a different kind of client or a different client set and also different employees. Yeah. And then so that worked well I guess from 2010 through 2013 14 and then I again started wanting more. So we we grew quite a bit. So it in 2014 had 22 employees and we were losing tons of money. So at the worst month was February of 2014 and I lost 50 grand in one month and that was hard.

[00:07:42] Yeah. And I said you know I don't come from a wealthy family. No one in my family graduated college. I didn't either. But you know and saying like oh shit this isn't going to end well. I ended up you know I had some consultants working for me. God only knows what I was doing. And so I ended up laying off a number of people we got down to about nine people. And I went to this conference in Orlando it's called Digital masterminds. I was cold called you know by this other agency owner and he's like look you know I found that there's value in being around other agency owners. And at the time I didn't really know any Yeah. And so I I went to this kind of like 30 person conference Armando and I thought it was great. You know it's people from all over the country. It was beautiful weather. It was great. And then I remember it quite clearly there was this guy who was supposed to get this talk about culture and his name was Jeb. So he gets up and is this tall guy and before I even heard him speak I thought I need your friends that guy I need to get close to him.

[00:08:40] Yeah.

[00:08:40] So he starts speaking about culture and he's writing all these things. He's got this soothing voice and he's really amazing. Oh he listens this podcast and will hunt him down and send him on I'll text him after it. So then I have told the story a number of times that you know events you know at the time I was quite good at fanboy ing you know if I wanted to be close to you or friends with you or what have you. You know I'd find a way. And so during this conference I would sit next to him you know but I would make it look like serendipitous second you know Jeff nice to see you again. And you know he was such a nice guy. He was so gracious and after his talk I went up to him and I said hey you know you talking about selling a hundred thousand on websites. I never thought of that like how you do that. And it was just wonderful and he showed me about this process this discovery process and over the course of becoming friends I think he said I don't think he expected me to take him up on it but he said hey you know if you're serious about this why don't you come up to Indianapolis and you can you know meet with my team and you can see the way we do things. And I said Yeah that sounds great how about maybe next week or the week after. And so I got my car I drove up there. I had no apartment I had no hotel to stay. I just drove up there and spent the day with him. And then I think he asked it someplace. So like where are you staying.

[00:09:56] I don't know. I ended up staying in his house with his wife and kids and and factional stalker here. Yeah.

[00:10:07] And you know we stayed up late till the wee hours of the morning is like playing records and it was just wonderful. And I and I loved the way that he talked about his wife and his kids and his family name such as like warm. Guy there and I call my guy like I'm gonna be like him. And and so I took you know a lot of the things he said and then I started trying to implement them with my team. He ended up coming down to Louisville. So he spent two days in Mobile with my team.

[00:10:34] And he told me he's like Look man you know you need to turn over. He basically told me in it fire everybody.

[00:10:41] And why. Like what was what was the inside. Well guess what. So. So what what were your takeaways and seeing his operations like what did you see him doing differently.

[00:10:49] So I think there were a couple of things one. There was a sense of calm. So my company had a sense of chaos. So you'd walk and I thought that frenetic pace and people looking chaotic everywhere and screaming and yelling and being loud was a sense of progress or was showing that we like we were doing good work. But I mean for a lot of guys like you know we're not solving cancer here. Yes. So there's no need for this frenetic pace and a lot of it took after kind of me and I to your point earlier I kind of hired people that were like me you know and they were kind of frenetic. And so I went there and I thought it was amazing. And I'd walk around in his halls were quiet and you know I talked to his people and you know they weren't like running late to the meeting to see me. They were just like Sure yeah I'll talk to you. And they were like warm and lovely people and profitable. You know the way they talked about their clients I thought was really great. And so you know it just it just seemed a heat this term because I hate business people use it but when they talk about a family I mean when they talk about this kind of calm approach where there's trust and they love. How about this a healthy family. Right. So that there's this sense of you know what when. When Sarah tells me that that's going to be done on Friday I believe her. I don't rush back in on her every day. I. It just works. And I thought I'd never really been in a company like that. So I thought that was lovely and I thought that was really wonderful.

[00:12:12] And and then he came down that I'd like to talk to you.

[00:12:18] It's like good lord and you can't say the opposite so to his credit he pointed at specific people in his and I think these people are really they could really be great. I mean other people know the good people. Yeah.

[00:12:29] Well it's not a judgment personally. Yes it's like Yeah exactly. They're not serving you well.

[00:12:32] Exactly. And we weren't serving them well. So we turned turned on most the people I know of those 22 people only three of them made it another year and a half. So he really turned over the whole team. And then we started this was another point. You know this whole whole idea of who or what got you here isn't going to get you there. Yeah. So so Taylor you know you guys both 20000 our Web sites you can't just take these same people in the same processes and build a hundred thousand Web sites so something it works. You've got to hire new people. You've got to have new process. You have to have a new way of dealing with customers eyes and never take clients. I don't know why I had this troll but I would never take clients like out to lunch or drinks or any of that. And that's a big part of big sales in the relationship in this music. And I didn't realize how much I loved it. So.

[00:13:19] So yeah I mean I could go on and a rule that didn't serve you very well. So yeah so. So that gave you kind of this transformation of the business and you know both culturally but also it sounds like from a process point of view strategic point of view like the accounts you're going after. How did you I guess from a from a sales and marketing point of view how did that transformation occur. Like how did you go from hunting hunting and engaging with people that you know previously you're looking for twenty thousand other websites two hundred thousand other Web sites like what was the change in your kind of sales and an initial engagement process.

[00:13:52] So one of the biggest things he pointed out was that I was spending too much time in sales for too little outcome. So if you called my office and you said hey I saw your name on line or I met you at a networking event or somebody told me to call you and we the Web site I would have an office manager or she would write down your name. All that eventually moved to more appointments system and I would meet with you I'd go out to your office. We would never meet at my office. I won't go out to you. And I was doing two or three of these a week so I was spending all my time largely outside the office going and meeting with people and it felt again the frenetic pace.

[00:14:25] It felt like a lot of progress because I was doing a lot of activity. But these people and he pointed it out to these people don't have a budget. And that was okay. I asked him a budget and they will give it to me. And he was yeah. So you gotta stop asking people for budgets you gotta stop. You guys are telling them the budget. And I was like What the hell are you talking about.

[00:14:42] He said he's like here's what you say you get on the phone and you say Hi my name's Taylor. He's like you never go meet with them. You get on the phone and you do a phone screening and you say hey this is gonna take 10 minutes. Hey Sam it's really nice to meet you. So what's your business how do you hear about me. But I'm like Okay that sounds great. So what are you looking for. Oh Nina web site. Okay. Sam That sound that sounds great. Just so you know here's where we operate. So we do a discovery process upfront that's usually five to ten thousand dollars and then that will take 60 and 90 days. We interview customers with this whole process. And then from there we'll go and we'll build out the website and build out the web. Can a Web properties you need maybe you take six to nine months that costs.

[00:15:18] 50 to 100 thousand dollars. And then from there we're going to do a digital marketing campaign and you know it goes on from there and it's three to ten thousand dollars a month. How does that sound. And they says and then you just shut your mouth because they're going to say one of two things Either they'll say OK SURE THAT SOUNDS GREAT THAT'S ME OR they self select out and they say oh me and that's way more than I want to spend. And you said and you wish them luck. And I said Jeff if I did that like we would have no leads.

[00:15:40] And he goes that's the point. Then you need different leads you need differently.

[00:15:46] Drunk people wasting all your time. And I was like Oh shit. OK. So we did that and then you know I had a couple of those calls and I was really worried. And you know all these people said no. Of course know. And then I got a guy a woman actually Christina.

[00:15:59] She said OK she's actually a current client that we had sold her a 20 thousand Web site. And we had lost probably 30 grand on it. So she calls me back. She's like hey we need the website of course. You know I'm selling her you know fifty thousand other things for 20 grand. Of course she wants it.

[00:16:15] I'll take it.

[00:16:17] She's like You guys did great work. You know it's such a bargain. Such a bargain. So she calls you back.

[00:16:22] She's like hey you know we want this. We had to choose a manufacturing business. She had another brand. And I said Christina we can't do the old deal. We have this new process now we're going to discovery. You have to pay us five thousand dollars to do discovery and she has what is that. And so what we're going to do these wire frames we're going to interview your customers Carol. We don't need that. We just my website and I said Well that's the only way we can do it. And I had somebody who was working for me at the time who told her all this. And she said no. And then I called her and we had this whole conversation. And was it Christine that you just had to believe me and you have to trust me. And to her credit she said OK fine we'll do it. And then we took that which she thought was gonna be a 20 thousand Web site ended up being I think was eighty three or eighty five thousand dollars. And at the time that blew me away I was like Oh my God you know I've hired a new creative director at that time a lot of things are really going well. Loves you. Thanks Jeff. And yes that that was kind of the beginning path to changing the way the business was.

[00:17:15] Well and I think that's a powerful story. All right. It is a powerful story in the sense that you you kind of have to you have to articulate and kind of manifest that before or define it before it's going to happen like it you needed to sit down and say OK look this is our goal. We need to shift the business to do these kind of projects and these kind of ways at this kind of rate. Now let's go make that happen. And I think that you know without that kind of planning and strategy and foresight and setting those objectives and then implementing you know you end up just getting more of what you've had before you know without kind of planning and intention you're just going to repeat the patterns and repeat the projects that you've been in. So I think that's that was a big change. And I can see why why it worked in terms of how you approached it. So let's talk a little bit about then kind of the next stage of growth because I know you know at some point businesses get to kind of the size where sort of the founder of the entrepreneur you know needs becomes kind of a bottleneck in terms of the growth of the business particularly around kind of the leadership and the management of the business. Tell me about the process for you in terms of putting together a leadership team management team you know bringing bringing people into the higher level decision making and management of the company. How did how did that play out for you.

[00:18:26] Well I think that there were quite a business coach who wasn't good enough for the plug.

[00:18:33] I had a business coach for five years and then end up getting and then I got another coach after him. And this business coach I talked to every Monday afternoon sorry every Monday evening and it was like therapy. I was also going through therapy.

[00:18:49] And so I also recommend that you recommend.

[00:18:53] And so I had all this therapy and coaching and you know I started to learn about all these mechanisms and things I didn't know about. And one of them was this idea of the lens through which we see the world and that there's this lens that I'm applying to different situations subconsciously. Let me give an example. So when I because I didn't have a great experience with schooling or with higher education I really discounted it when it came to other people. And so unless you went to like Harvard RMIT I didn't care where you went or what you did. All I care about was experience. And you know it served me well in a number of ways but a big gap that I had is that I thought that to be a good leader you know and I didn't think that I was a great one either but being a leader you know you had to kind of go through the the trenches and just do the hard work and figure it out. And now I think that you know now with hindsight I think that I would have benefited more from coaching and kind of leadership training and sales training and sales coaching of my team. So I mentioned that because I tried to institute a number of things that Jeb had told me and others you know like business coach and whatnot but I was just one person.

[00:20:05] And so I'm trying to explain to my head of Marketing How to Be a good leader and there's no way that I can explain that you know she at the time you know she actually turned out quite well but a number of other ones. Really unfair what I was asking them to do. You know I need you to figure out a sales process. Well this guy had never done the sales process in his life. What's he going to google it and figure figured out I was setting up a lot of people in the early days for failure. Yeah and then I would blame them. All right. They called me and that was the wrong hire. And I think a lot of entrepreneurs do that. And I think really few people could have been successful in that situation including me. Yeah. And so over time I think I got lucky. You know I I started working with I worked with this woman who was a director of marketing and an accounting firm. And she was one of at the time she's one of my favorite clients and she told me she was leaving the firm.

[00:20:54] And I said What are you gonna do now. This is a guy who's gonna do some freelance consulting. And I said Well I'll be your first client. Yeah. And so it brought her on as a consultant and then over time she ended up taking over the business really and she became president of the CEO of the company. When we sold that with the company to the acquiring firm. So I think in some ways you know for her which that this was a success story that there were a lot of examples of how poorly I did it setting people up for failure and you know when I let them go or when they quit they said some not nice things to me. So you know I learned some learned some valuable lessons there. But in terms of finding good kind of team members I don't think I was actually all that great at it. I think that I think I was just okay I'm really better at it now just because I've done a lot more of it. But I think I would have benefited from people who are much wiser than me helping me in that process.

[00:21:46] Yeah but I would say having worked with a lot of founders and a lot of CEOs it's not too uncommon. And the problem I think is that as you know as a as an entrepreneur you know we're kind of good at solving problems like we like that. OK. Well let me figure it out. Let me you know apply my knowledge my smarts my creativity I'll do some research. Like I'll figure it out. And so we tend to be I think at some levels overly self reliant on our ability to get to solve these things. And it's you know that's good at certain levels and it's good when you know in early days when you need to be scrappy and needed to kind of get things going but yeah it ends up I think working against us later when we really need to find people smarter than us that can come in and really add to the knowledge add to the experience and create something that we really just can't create with our own experiences like we need. We need to leverage those things.

[00:22:37] I'd be curious to get your thoughts on whether I think there's a kind of practical sense but I think there's also the awareness of the kind of mindset. I think there's a shift.

[00:22:44] I think there's a shift that happen for entrepreneurs that reach that point and they change they kind of change their thinking around it. I mean did you notice what was there. I mean you mentioned this work you've done with a coach and was there a point at which you just kind of became aware of. Oh I see I have that. That is something I've believed or a way that I have approached this and I need to probably change that if I'm going to get to the next level. Did you go through that experience.

[00:23:05] I think it was a slow shift. You know it was there wasn't kind of this one aha moment. There was you know there were a series of probably 20 of those and a lot of them involved negative feedback. So a lot of it involved you know I mentioned people with the or I don't let them go and they would say to me they were hurtful things that may or may not have meant them to be hurtful or a client would leave or I would pitch a potential prospect and I thought man we are the best company for this. And then you know they would tell me no for whatever reason or they pull out at the last minute you know a lot of the learnings came from pain you know a lot of the learnings came from why I don't want to you know and then I would leave that meeting or you know or that event and remember how I felt. It's like oh wow that really sucked. I don't want to feel like that again. So what can I do differently next time. And it was just a series of those you know and I continue to have those.

[00:23:57] Yeah ironically they don't stop. They're just different now.

[00:24:02] Yeah well I think there is there's a choice that I think we all end up making. You know you can take that feedback and you can blame something else you can kind of blame them. Well that was their problem not mine. You know you can kind of justify it you know you say Well yeah I get it but I was in this situation. So you know I kind of made sense or you know you can take responsibility and you can say All right well maybe I need to do some reflection here and figure out like is this working for me is not working for me. What else might I do differently. You know how would I implement that. It's self-critical without being harsh or being kind of judgmental. It's just reflecting on your own kind of role in that situation role in the process and deciding whether or not it's serving you well. And I think that way.

[00:24:41] And one thing that's so funny. It was not funny at the time but a funny retrospect story is this guy who called our office and he said hey you know I need your Web site. And I said Okay great. And this is before you know before I fully implemented this change a process cycle out to his place. This guy owned a retail store that sold fishing supplies basically and water related things. And so I go in there you can't make this up. And so. So this woman who is really nice and she kind of greets me and she says okay you know we're going to be meeting back here. That's great. And she said the owner of the item just a second.

[00:25:13] I think a cheap thing drink nothing. So the owner himself is kind of like. This guy kind of scruffy and he says Hey I wanted a Web site. And at the time I was working on changing my sales approach again. Bit by bit. Big steps. Just. You know what I'm gonna try this new thing today and so I tried instead of asking him a budget. I was trying I'm going to state a budget. I was like look at what you do I think that would be he won an e-commerce site. And I think that I decided on 50 grand. And so I said hey you know Steve as you know this is this has been great for my understanding. You want this in our experience what we you know this is. And I was really nervous and saying it. Yes. For Tubby Brown. Fifty thousand dollars his web. And he could not have reacted more violently. And he slips out. I'm sorry. He stood up and he goes. Fifty thousand dollars. I mean I could see Toyota like oh my god Toyota spending debt. Oh that's unbelievable. And he just goes off on me. And I couldn't understand it. He goes because you know what. The last guy I had built my web site I would hire him again. And I said Well why don't you. You know I paid him two hundred dollars and that's what I. Why don't you quit. And he's he said well I called him but he's in jail. And I thought that I was being punished. I was like surely this is it true. But it was like this guy was this nets and they're feeling so down. I was like Oh.

[00:26:38] And that really didn't work. And what did I do wrong. Well now that company went out of business within a few months. Yeah. Not surprisingly. But but the reason I tell that story is because it's kind of funny but B it's it's like the learnings isn't always from us. Right. So the learning isn't always that I did anything wrong. The learning may have been that sometimes we're not a good fit. And regardless of what I would have said or how like how talented I am or how skilled my ability in delivering these results. He wasn't ready for it or their company wasn't a good fit. So I think that there's that element too to be careful about where to pull the learnings from.

[00:27:15] Yeah. And that was probably the learning as you know delivering that number over the phone rather than spending the time.

[00:27:22] Eh. So that saves time BS so that you avoid bodily harm. That's a good one. I like it.

[00:27:30] That's all I wanted to chat just a little bit because I know you you you did an accent you sold your company you had mentioned it a little bit before and you know I'd be curious on the kind of more of the emotional personal side you know because you know we talked to folks about you know the strategy for selling and pricing and the negotiation process and all that you know. But I think there's a whole kind of personal side to this in terms of you know being launched or being a founder. And I'd love to get you know just a couple of thoughts or takeaways from you in terms of you know the process the personal emotional process of going through the sale. Like what. Any surprises anything that you learn that worked well for you in terms of you know your connection to the company if you had a strong connection to the company. You know from an identity point of view or not was it easy for you. What was it like on a personal side.

[00:28:12] Yes. So this is a good question. This is a question that I don't think it's asked enough when when it comes to exit. So. So to your point a lot of people focus on terms that they focus on you. How was the deal structured. How did you do that. So what was the and kind of tactical things but not enough people are talking about this question you just asked around. Well how did it feel. What was the you know you exited the business. And what was the emotion of that. And for me I was not prepared for that at all because so few people talk about it. So there were a series of things right. We had a buyer who approached us based in Boston at the time I was doing a lot of traveling and I had this very small window is going to leave for Europe. And so it's very small window where I could meet with them. They're based in Boston I'm based in New York. The company I owned is based in Louisville Kentucky. And the the central point for all turned out to be Nashville Tennessee. So I flew into Nashville for 24 hours when I had known the buyer. We had worked with them on a number of projects and so we fly in we go out drinking and then the next morning hung over at the hotel like breakfast bar they say you know look we'd be interested in and and buying.

[00:29:28] So why don't you send over your financials and let's you know let's get this rolling get this deal. And I said OK so I had to be careful what I say here. But there were there were a number of parts of the process that I thought would be really structured that turned out not to be right. So this buyer had someone on their team who had bought hundreds of companies as part of being a public entity and that really impressed me I was like oh wow you know co-founded a business and the billions of dollars. And so I really kind of was like wow this is I was almost in all of that. And so over time. Well then I flew to. I was in London. I was in Europe for a little while. And I remember I got the letter of intent and I had agreed to the letter of intent to take out our financials and everything. And I was standing in front of the Eiffel Tower in Paris. And I was there with my friend Jeff and we were. That was I don't know. It was happiness. There was a sense of happiness but also a sense of accomplishment and pride and a sense of like almost completion. Little did I know that that letter mishap meant nothing.

[00:30:35] And that you know this sense of like or it this is the best I'm going to do. It's all gonna help.

[00:30:43] You know so many lessons I learned from it. We saw him. We're in Paris.

[00:30:48] And it was it was late in Paris is probably 11 p.m. eleven thirty and sweet. We found this restaurant where in this touristy area of town we find this restaurant we go in there. And Jeff he's like two we should celebrate when we get a nice bottle of champagne.

[00:31:01] So we buy a bottle of Christians Crystal Crystal.

[00:31:05] Crystal I never had crystal in my life. And so. So we order crystal we point to it on the menu we say. And they bring out this like 40 dollars picture and they open in front of us. And they start pouring the champagne. And I'm like Crystal it's kind of crappy. And to my buddy's credit Jeff goes I don't think that's crystal. And so he says to the waiter Hi Crystal. And I said no this is the crystal. You guys clearly can't afford Crystal. Just like Schwartz. Exactly. So anyway we ended up getting Crystal and we drank a whole bottle was delicious and amazing and highly recommended.

[00:31:41] But I tell that story because I was you know fine like the rest of the Europe trip is great. I was having calls with the buyer pretty much every day talking to different things. And it was great. And to what you said that was the peak. Right. And so from there. That was in April of 2018 until we closed at the end of August. I just experienced this wave of emotion that started with kind of like pride and amazing this. And you know towards the end I went to emergency room with chest pains. I was thinking I was having panic attacks and heart attacks. I I felt immensely alone. I was like wow I'm an idiot cause I didn't you know check this or check it out or I didn't ask this person on my staff these questions. I trusted the people who worked for me and the people who ran the business and I kinda let some things go. And you know I won't go into detail but there were a lot of things I would do differently. And one of them is a forensic accountant. So I wish I had that before I entered that letter of intent or at the very beginning before due diligence that paid a forensic accountant five or ten grand however much it was to come in and really audit the books somebody who had never heard of our business somebody who had no vested interests who just would come in as an outsider and say you know what's going on here. Because had we done that and had had we had I hired a good firm to do that I think it would have made due diligence go so much more smoothly. And you know a number of things kind of came up when during due diligence that would have been a whole lot better had I been the one who could have found out about it you know versus the buying firm or what have you.

[00:33:17] Yes well what I mean what am I general suggests to folks when they start talking about an exit is you know a year before you're going to do an exit you know you do that you know essentially have a forensic accountant or go through a mock sale you know and have someone that can come in and do you know basically do analysis of it. And I think yeah I mean I had similar things I was like you know we're looking at oh well based on the way your health insurance is structured you know there's one hundred thousand dollar liability on here that we need to like take off the you know the offer and stuff.

[00:33:44] I mean it was like and I mean you know not I mean some of it is just at least I would have been you know emotionally mentally prepared for it wouldn't have been like at the eleventh hour you know 24 hours before we're trying to sign something something comes up and now I've got a I'm in the hot seat like do I do the deal do I pull out and pay a hundred thousand dollar penalty you like you're not in these kind of stress situations but also you can do some things about this stuff like OK well maybe we should change that or maybe we should restructure how we're doing those things so this could really help valuation. So yeah. And you know I guess I'm not sure I have I've had too many people end up in the emergency room but I certainly had you know founders that are you know exiting that have gone through a significant emotional stress and the other one is you know family stress. You know I mean I certainly happened to me when you know you're dealing with family and kids and spouses and stuff like that and you know trying to figure out you know try to explain some things to them and like you know what is what's the deal going to look like what is going to happen. Is it going to happen. You know all that can just add to the process and add to the drama.

[00:34:40] So well and good intentioned friends and family are. You know if they know about the deal every time they see you they're asking. Yeah exactly. And the thing is that I thought about that deal and worked on that deal. Twelve hours a day that's sort of the last thing I wanted to do when I go to dinner.

[00:34:56] Was to talk about that. Can you not talk about it.

[00:34:59] I mean not talk about and they're like you know no one's doing it malicious. Oh yeah. They're they're curious. They support you know and they're trying to be supportive. Yeah I remember that kind of chest pain story had to be in Boston for this meeting with the acquiring firm took train from here up to Boston spent the day there took like the midnight train. Back get back to New York at 4:00 a.m. at 7 a.m. flight to San Diego. It was a disaster and then I landed San Diego. My brother got his MBA. He was graduating and signed there for like three or four days and the whole time like my chest and I couldn't tell anybody and then I was like I was trying to find a way maybe I could get to urgent care or something in San Diego but don't want to worry my family or myself too ya know. So then I get back on a plane fly back to New York booked with Zach doc on the plane an appointment as soon as I landed so I could go. And you know it ended up being fine thankfully. Yeah but you know something that really helps a lot. I was talking to people who had sold and there's an EO member getting involved and Entrepreneurs Organization as you are as well and there's an EO member who I met you know what name somebody sold three companies and done quite well. And I met him at this board that measurement and events and I came up to him and I was like hey I'm going through a sale. I don't feel well. Could you do coffee with me. And he said Sure I do. And so we went to coffee and we spent three hours at this coffee and he told me at the end of the coffee Miss Taylor listen to me everything you're doing is all normal.

[00:36:34] It's like the way that you're the way you're feeling this is normal that the emotions that you're feeling that's normal. He has Taylor I've had chest pains a lot of my friends who sort of companies they had chest pains. He's like It's not glamorous but it's normal. It's fine. He goes he's tape threats. It's ok like you're gonna make it he goes even if this deal falls apart. You're still a good person and it doesn't mean you know that you're a shitty person or a bad business man or any of this and you're still a good person it's OK. And that was just so helpful. And he's like. Plus you're really young. It's like you can have more.

[00:37:08] Yes. The good news is you're going to do this again. You think this is bad wait wait till it's a hundred million dollar deal. It's actually really good pain and pain and that let go.

[00:37:23] So I think that that that bonding that comes from the others who have been through it can be so helpful if just to say hey you're doing great. This is normal. All these things and feelings this is all normal. It's OK you know.

[00:37:35] Well I think I mean unfortunately for both of us you know that we ended up pulling it off. Does know a lot of people end up going through this and then the deal falls apart and now they're back in their business and you know oftentimes the you know the impact is taking your eyes off the business I'm trying to get the deal done. You're right. You end up with no no deal and then a business who's not doing so well because you haven't really been paying attention to it for six months so you know there are other outcomes that are actually more challenging or lead to that and you know more challenging endpoint.

[00:38:03] So maybe the silver lining but this has been great we're gonna have time if people want to you know learn more about you have experience you know questions what's the best way to get more information so you can go to my Web site and taylortrusty.com t r u s t y dot com and on there you can try and contact information for me I'm pretty fairly active on Twitter. I just post articles that I think I read a lot now have a lot of time. So hey just post articles about tech and business and email address is on there and feel free to reach out.

[00:38:36] Perfect. I will make sure that you're also on the show notes Taylor. Thank you so much for taking the time. Thank you so much for the for the conversation I am I really appreciate you sharing the details and the personal aspect of of of these stories with us. It's really it's been insightful and it's been a pleasure.

[00:38:52] Pleasure's all mine. Thank you Bruce.

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