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Podcast: The Emotional Side of Selling Your Small Business with Jamison West, Co-founder of ConnectStrat


Jamison West S2F Podcast Image

The Emotional Side of Selling Your Small Business

Jamison West is the entrepreneur of entrepreneurs.  He is also someone who is very willing to share his journey in a way that is relatable and authentic.  I don’t know any business owner who always “knocks it out of the park”.  There is always the rollercoaster of wins, losses and draws.  That’s what Jamison is able to bring to his latest endeavors as he aims to provide a compass to other owners.

In this podcast, we talk a lot about his new book, The Emotional Side of Selling a Small Business, a clever fable that tracks Alex, an owner of an outsourced IT services company, who is grappling with the opportunity to sell his business.  We ride the rollercoaster with Alex from elation to terror as he tries to figure out an outcome that will serve the life that he is trying to design.  This is a great follow-up podcast to Episode 44,  Things to Consider When Selling Your MSP with Randy Katz.  Jamison’s book brings you inside of the head of the business owner real-time.

We also talked with Jamison about his coaching company, ConnectStrat.  ConnectStrat provides guidance for outsourced IT services owners to help them build a company that will achieve their goals.  They start every client with a foundation day to really get under the hood to answer the question of, “Why do you want what you want?”.   They then move into some of the tactical aspects of orienting a company in service to an owner’s life design strategy.  What I so appreciate about Jamison is that he has dedicated himself to supporting other entrepreneurs and leveraging the fullness of his own experience as a guide.


In this Podcast episode with Jamison, you will learn:

  • Why he wrote his book and the impact he wants to make
  • How to think about the considerations in your life when selling your business
  • Why hope is not a plan and the value of good strategic coaching
  • What guys like Jamison are afraid of (yes, we all have fears)

Enjoy this episode and get in control of the life you are trying to create for yourself, your employees, your customers and your family.

Listen Now

We are fortunate to have Jamison available to spend time with us on this edition of Stride 2 Freedom. If there is a speaker you’d like us to interview, click here and let us know. Stay well. Stay safe. Stay healthy.

Show Notes and Links From Episode:

Jamison West LinkedIn

The Emotional Side of Selling a Small Business


Jamison West Email

Episode Transcript:

Russell Benaroya: Hey everyone. Welcome to the Stride 2 Freedom podcast. My name is Russell Benaroya, and I’m the co-founder of Stride Services, a virtual back office, bookkeeping, and accounting firm serving hundreds of clients around the United States.

This podcast is designed to help small business owners focus on growth and innovation. In other words, focus on those things that inspired you to start your business in the first place. We call it your genius zone. We do our job on this podcast when business owners feel like they have the trust and confidence to build the right team of partners around them that will help them grow. Thanks for joining. Let’s go.

Hey, everybody. Welcome back to another episode of the Stride 2 Freedom podcast where we help business leaders get and stay in their genius zone. What’s your genius zone? It’s your superpower. It’s what you do that feels effortless to you where you’re at your best where people wonder, how are you so capable? It is where you feel free.

My name is Russell Benaroya, and I’m your host of the podcast. This podcast is brought to you by Stride Services. As you probably already know, we’re an outsourced bookkeeping and accounting firm with the express purpose of helping people with a thirst for continuous improvement achieve their highest and best use.

Our highest and best use is helping business owners use data to make better business decisions. We typically do that for outsourced IT services firms, marketing agencies, and consulting firms. I am off the hook excited today to welcome Jamison West to the podcast. Hey, Jamison.

Jamison West: Hello.

Russell Benaroya: So nice to have you here. Jamison and I met many years ago at an Entrepreneurs’ Organization event, and I just knew that we would cross paths again. Jamison has a certain energy, a certain presence, a certain magnetism about him. I said, “I know I’m going to see this guy again.” I didn’t know it was going to be on a podcast. But who knows?

Today we’re all up in each other’s business on a bunch of fronts, a couple that we’ll talk about today. But the reason that I wanted to bring Jamison on was twofold. The first is Jamison’s coming out with a new book, and we’re going to talk about the book. It’s super relevant for business owners, and I’m excited to dive in.

Jamison is also on his third or fourth act as an entrepreneur, and he’s the co-founder of a company called ConnectStrat that helps business leaders in the IT services space plan for and achieve their dreams. What do you say we rock and roll?

Jamison West: Let’s do it.

Russell Benaroya: Okay, awesome. What is something, Jamison, that I can celebrate with you that you’re just really excited about right now?

Jamison West: One thing just struck me that I’m excited about is you and I’ve got all these funny connection points, an odd timing with EO, serial entrepreneurs. We’re always having these conversations, “Wow, this keeps connecting.”

When I realized and I read it but then I just heard you do it again, one of my favorite things to talk to people about is their genius zone. I use that exact link literally on the exact day now. I don’t know if it’s because we were at the same event in EO Seattle where you had to break out and discover your genius zone. It was a facilitated exercise.

I think it was in Portland five or six years ago. I’ve never forgot. It was probably one of my favorite things I’ve ever done. I think that for me, it’s celebrating that I know I’m in a place right now where I feel like I’m in my highest and best use and living my genius zone. So that’s pretty exciting.

Russell Benaroya: Yeah, awesome. You’re a busy guy, I can tell. You got buzzers coming everywhere.

Jamison West: I do not know what that is.

Russell Benaroya: Oh, it sounds like it’s a Skype invite.

Jamison West: Yeah, I don’t use that. Sorry.

Russell Benaroya: Everybody should know people are trying to get ahold of Jamison, so we are honoring this hour together. Okay. What is something, Jamison, we can empathize with you on that is draining your energy right now?

Jamison West: Wow. Well, right now I’ve got a few things draining my energy. I think that I’m always trying to pay attention to that and purge those types of things. I think the main thing that I could talk about that has been a bit much for me is I am currently owning, running three businesses which is a lot. I work extremely heavily as a subcontractor and coach, and one of them is ConnectStrat. A little bit along with being the president of the Entrepreneurs’ Organization of Las Vegas right now.

I feel like I have five jobs which is about four too many. A little bit draining but definitely working within tension on mitigating that so that I enter 2022 a little more refreshed and with more energy than I feel like I’ve had over the last six months. So a little overwhelmed but doing some good work to mitigate that

Russell Benaroya: We can empathize. I’m sure we can all empathize. Getting back to your genius zone, let’s talk a little bit about that and how you’ve applied that to the businesses that you’re involved with today.

You’re in so many ways a legend in the outsourced IT services or MSP market. You’ve built a couple of companies. You’ve exited some companies. You do not tend to stop. You want to help other entrepreneurs achieve their dreams. Where does all this come from for you? And why are you so clear that, yes, this is your genius, this is your superpower?

Jamison West: This will be really relevant, I think, to some of the rest of what we’re talking about. When I look back, I think I’ve probably had eight or nine businesses. I had a main business in the course of my professional career, a main business.

There’s so much that you learn on your first big go round and exit, many pieces of which were not my genius zone. I think that that’s natural. Then what happens is you get this opportunity once you sell or exit that business, you go into act two. Act two for me doesn’t mean per business, but it’s just act two of my professional career.

I’m in the same vertical. I’m working with a lot of the same people. I’ve been fortunate to have made incredible relationships and just gained a bit of a reputation in the area that I appreciate and I’m thankful for, but I was also able to enter my second act with intention.

Much easier for me to get involved and there’s opportunity galore around me right now, but I get to pick and choose those things that I’ve got passion for. So it keeps my energy high. I’m a naturally very high-energy person. And now that I get to apply it against the things that are in my genius zone, that’s a beautiful thing. I don’t get mired in the minutiae of stuff that I realized I could do but didn’t truly enjoy or have passion around. So it’s–

Russell Benaroya: How would you characterize your GZ? How would you characterize it yourself?

Jamison West: I went to the University of Washington Foster School of Business. I am not an E-Myth entrepreneur. My uncle was a massive entrepreneur. I’m telling old stories. I think I was in seventh grade when I had my dad ask me what I was going to do. And I said, “I’m going to graduate from the University of Washington business school in June of 1992, and then I’m going to go on to own United Graphics. And I’m going to go on to own this business. I’m going to be an entrepreneur.”

Well, I did graduate that month from the Foster School of Business. I was told, “You’ll change your mind 100 times.” That’s 10 years away. I did not. I stuck with it. But an E-Myth entrepreneur is like that technician that finds themselves owning a business.

95% of the IT services people I work with are E-Myth entrepreneurs. They are actually engineers at heart that became business owners, and they’ve had to learn that through experience. It was a little different. My genius zone was really around people. I love managing and working with people and leaders.

I realized that that kind of background I had and maybe a little bit of that natural EQ that exists there just I love to help people especially in leadership positions get stronger and then really finance is my other life. The numbers just click in the back of my head. I’ve been the CFO of pretty much every company I’ve been involved with. It’s the last role I let go because it’s what I’m so naturally inclined to do.

Russell Benaroya: Then you build a business most recently or in the last year or so called ConnectStrat which seems purpose-built to help you express all of this learning and creativity and energy in service to helping manage service providers achieve their dreams and find their zone and be successful. Talk about that vessel of ConnectStrat and what it’s doing for you and doing for the community.

Jamison West: It’s interesting. I talked about intention, but there’s a little bit of accidental in there as well. But that’s part of what we are. I accidentally–

Russell Benaroya: Always a little accidental. Always a little bit of luck. You are a lucky person. Yeah.

Jamison West: The background of ConnectStrat is really interesting. I’d sold my IT services business in Seattle and moved to Las Vegas about four and a half years ago. I’ve since taken the CEO role of the company I helped co-found, a SaaS company called SmileBack. And I helped co-found a company called Teamatics and another one called TimeZest.

I’ve got these three software companies going, and I’m not involved with Teamatics anymore. So that’s kept me busy. But it wasn’t earning me the income that I needed, so I began consulting with leaders on the side using primarily the EOS methodology, Entrepreneurial Operating System methodology. I was working with people here in… Somebody really wants to reach me. Sorry.

Russell Benaroya: Yeah, we know we’re talking to a popular guy.

Jamison West: I never get calls on Teams. Hang on. I couldn’t even figure it out. What I did is I started helping people using their methodology, which just clicked for me. I leveraged scaling up in my IT services business from Verne Harnish and then switched to Traction EOS from Gino Wickman.

I love putting a process, a system really is a better term for it, in your business. E-Myth entrepreneurs need that, but I think every entrepreneur needs that. I was thinking about the systems, but I was really being very horizontal and local area here in Las Vegas just helping some friends in EO and some other…

I had this epiphany late 2019 that all of these IT service providers, and it was just growing. It was becoming more popular. EOS was exploding in the industry. And I said, “Who do I go to? I’m in Raleigh in North Carolina. I’m in San Francisco. Who do I go to?” And I was like, “Well, I don’t know. Who are the local people who can help you? And can they spell MSP?”

More often than not, there wasn’t somebody local who was really focused on the whole nature of what that is. Doesn’t focus on a vertical. I went back to my own coaching and counseling and said, “Let’s create a consortium of people who do this type of work focused on this vertical.”

Very rapidly it turned from a marketing consortium into, “Wait a minute, this is a real opportunity to create a legit firm.” And that’s the luck piece. The other luck piece in all of this is we immediately said, “In order to do that we can’t have these coaches work purely within their geographic area. I can’t have 10 MSP clients in Las Vegas. It’s competitive. It’s uncomfortable. So let’s figure out how to deliver these services virtually.”

This was two months before the pandemic. We had put all these systems in place and started coaching people virtually, predominantly, and then COVID… There was a little pushback from clients. Then the pandemic hits, and the pushback goes away. So our firm over 2020 just really exploded, and we figured out how to… We already knew how to talk to the industry, but now we knew how to deliver and refine what we wanted to deliver virtually. And the timing couldn’t have been better. So that’s the luck component.

Russell Benaroya: If I am an IT services owner, what am I walking into? What am I feeling prior to engaging at ConnectStrat? What am I walking into when I engage with ConnectStrat, and what is my desired result as a function of having a coach through ConnectStrat? Walk us through the journey.

Jamison West: Here’s what we found. It began as an understanding of what EOS does well and completely misses out on. All of those moral entrepreneurial coaches were like, “Wow, this is missing some significant parts. It’s beautiful what it is, but it’s missing some major components.” So we began talking to our clients and asking, “What?” You hire somebody to help you with your strategy. You do some analysis to peer groups. You have your EO. Maybe you’ve hired an EOS person. You put all these pieces together then no one of them is holistic.

What they’re feeling is this disconnect between what they want, how they run their business, how they get their leadership team on board and everybody else aligned and start with intent saying, “What are the outcomes that I want?” and driving materially towards those outcomes within the business.

When we assess where they’re at, each one of these areas is maybe at 20 or 30% of where it should be. It’s overwhelming to step back and say, “There’s all this stuff going on. I’m not a trained entrepreneur. I’m an E-Myth entrepreneur. I’m an engineer trying to get a bunch of people to…”

Some of these companies they’ve grown to $10 million in revenue run by an engineer who has no business background and is amazing at what they do. But they’re missing significant components, and they don’t really have the background to build those out.

As coaches, what we’ve done and said is take a step back and think about from an entrepreneurial perspective, what do you want out of this? Why are you here? Why did you build this? What’s the purpose? Financially, it’s certainly a component of it. But it’s not just the finance. What do you want? Why did you build it? And what’s the outcome? How do you move yourself from having a job working for the business and then making the business work for you?

We spend time in this legacy mentality. We call it Founders Day, and we just talk to the owner and founder and really dig into those questions, get to know them deeply. We have four pillars. Our first pillar is what we call the impact pillar, and it’s all about that life legacy. What’s the impact? Personally, family, community. What’s the impact that the owner wants to have through this vessel of their organization?

Then we move into the leadership team. We want to translate from the owner, “What’s the vision you have? And how do we get your executive leadership team aligned and clear so that you’re all really clear what that North Star is? How do you want to behave? What’s the culture that you want to define?” Because I think as entrepreneurs, we have the good fortune to do what we want to do with the people we want to do it with. It’s one of the reasons we become entrepreneurs. When you’re an employee, sometimes you have to pick your employer around that. But you get to design that as the entrepreneur and owner. It’s a beautiful thing.

Then the other two pillars. So that’s our vision pillar. We then move into the strategy pillar. Where are you uniquely different at? Where’s the industry going? How are you going to get there? How do you mitigate SWOT type work? How do we make sure we’re mitigating risks and doing all the things we need to do to be relevant long-term? How many business owners are in the IT services space? It’s just massive, who are heads down focused on the work at hand and don’t see security or cloud coming at them as a massive change in what they need to do and they’re not being strategic about how they’re going to approach it and get ahead of that wave.

Then third or fourth and finally is what we call our execution pillar which essentially looks a lot like EOS. How do we get annual goals or Quarterly Rocks? How do we just execute against that strategy? So that’s our holistic thing. At the end of the day we’re coaches, but we coach them constantly through that process.

It just gives them somebody outside of their internal work circle to confide in and get accountability and coaching from who puts together this entire spectrum of what matters to them in the business and gives them confidence that they can increase their maturity level across each of those four pillars and grow towards their intended place whether that’s an exit or an employee purchase or handing it off to one of their children or whatever it might look like. They now can work towards what that needs to look like definitely.

Russell Benaroya: What would you say are the three adjectives that express the feelings that a business owner has before they start working with you? What’s going on inside of them? What are those three words that are driving them to say, “Gosh, I want to do something different. I feel the need to do something different than what I have been doing.” What are three adjectives that explain it?

Jamison West: I always love trying to figure these ones out. But I would say uncertainty is a–

Russell Benaroya: Uncertainty. Yeah.

Jamison West: Uncertainty, fear, and then anxiety. We find that so many of our clients are coming and when they first hire us, they’re coming from a place of uncertainty about the future. They’re fearful about all the risks that there’ll suddenly be which is loss of employees and security right now are huge topics in our industry. So there’s fear about, “How well am I structured? Could the rug be ripped out from me today?”

Almost all of our clients are suffering. Not all but nearly all of them. And then that last one, that anxiety over… This is a stressful thing we do. Many are losing sleep at night, and they just want to have that extra layer of confidence and focus that they can move forward.

Russell Benaroya: Fear is a very natural limbic system of reptilian emotion. The decision to work with a company like ConnectStrat is a courageous move when you have fear. You can be scared and you can retreat or you can have courage and accelerate. You’re creating a path to acceleration, which I love.

Now let’s talk a little bit about how you are institutionalizing your legacy. I want to move off ConnectStrat for a minute and talk about this book that you have written, The Emotional Side of Selling your Small Business. You gave me the gift of an early lot.

I got to learn about Alex and his journey. He wrote this wonderful fable of how somebody moves through the emotional side of considering selling their business. Talk a little bit about the book, where it came from for you, and what impact you wanted to make.

Jamison West: Thank you. First of all, I appreciate your support in all of this. It’s been an interesting journey. When I sold my business, I owned it for 21 years up in Seattle. IT services business. I acquired four other IT services businesses. I did a rollup from 2010 to 2012, and I sold it in 2016.

What I realized when I did that rollup is on the buy side, I got maybe a little overly aggressive and excited about what I was building. The last acquisition didn’t go well, and I won’t get into the details. But it became very scary for me, and I almost lost the whole business. It shocked my system. I talked about that first part of our career and the second part of it, phase two of our professional career.

This was the end of phase one for me. This was that impact of going, “I’m not doing what I love doing.” I decided to sell. And fortunately, I was able to really recover from those acquisitions that were extremely profitable in 2015 and the timing felt right. I was very tired.

I spent 2014/2015 really listening to some people who were interested in potentially acquiring. My ears opened up. People knew who I was. I built a good business. Not a great business but a good business. And so I went down the path of selling, and ultimately that culminated in a sale in March/April of 2016.

What I realized in that journey were the advice, the people, the books, the education, everything that I had at my disposal to help me through that was about contracts and the P&L and valuations and the legality and tax implications. And it was all very business speak. It was very tactical, it was very financial, diligence, all of these components.

Nobody told me the depth that it hit me or the challenges I was going to have that had nothing to do with the value in the sale itself. Just going through that last three to four, there was some excitement when I started, even like going through the book. I don’t need to be ready.

There was this excitement in the idea. But from that moment I got excited about, “Wow, I could actually have something of value here. Actually, I can do something new with my life and exit this and get somewhere else.” But from that moment when I started to get excited and realized that that could happen to ink it on paper and getting the check in my bank account was just a shocking set of… It was the biggest emotional roller coaster I’ve been on in my entire life.

When I was done, I’d been asked to… I’ve sat on some panels. I’ve spoken about it. I’ve been at conferences. I’m a very transparent person. I get that through EO. I’m a one percenter, and I’m just going to overshare. I started talking to people about how complicated and difficult it is. I didn’t hide it. I was very open about it.

I was asked to speak on it a fair amount. And then finally my mentor who also wrote the foreword for my book, Arlin Sorensen said, “Hey.” He challenged me a little bit, and I told him, “I think I’m going to write a book about this.” And he goes, “Okay, you should do that.”

Then I publicly said, “I’m going to write a book.” I think it was the beginning of 2019. I rarely say it publicly. So it took me two, actually three years. I was supposed to add that there was a big event at the end of 2019. I hope so. He said, “You have your book ready. We’ll give out copies during your session.”

Here I am two years later. Just published the book. So I failed to get it out in time but just two years later, but that was the journey. I didn’t feel there was a resource for people that addressed the money, the value. It’s like all that becomes obvious. There’s a lot of resources. I didn’t see a resource around the emotional components, and that’s what I decided to share.

The fable isn’t my story necessarily. It’s pieces that might sound familiar to people who went through it because, of course, I borrowed from that. But I borrowed from many others as well. It’s not just for the IT service. It happens to be an IT service, but it had nothing to do with… The journey is the same no matter what kind of business you’re in when you go. An entrepreneur is selling the baby you’ve raised. It’s fraught with challenges that you didn’t see coming.

Russell Benaroya: What are you hoping that readers take away after absorbing the message of the book? What are you hoping for?

Jamison West: I hope that they can… Again, we talked about intention versus action. My hope is that they can take the fable and the case studies and be vastly more prepared for that journey than they would be otherwise to the degree that it mitigates the negative emotions that they can actually rise above that fray, have a list of non negotiables before they go into it so they don’t get…

You could put yourself at an extreme disadvantage by becoming so emotionally invested in the outcome that you lose the purpose and the intent along the way, which I’ve seen happen so many times. You can be taken advantage of by a bad player. But if you can get ahead of all that and understand the pitfalls and set yourself, have a plan… Because these are things that most people don’t even see coming.

You’re hit with it one day, and then you’re emotionally reacting and you don’t have time to do what you could have done had you been prepared. So I just want to prepare people for the journey.

Russell Benaroya: We had a guest on the show a couple of weeks ago, Randy Katz, from a firm called Synesis Advisors. He’s a mergers and acquisitions broker, and he’s worked on some many small businesses, certainly IT services included.

We talked specifically about IT services. He challenged me, listeners on the call to answer the question, what is the asset that you’re selling? And being clear on that asset. The distinction he drew was, hey, if the asset is you, not recommended. But if the asset is you and you’re at the center and everything revolves around you and somebody’s essentially buying you and if it wasn’t for you, the business wouldn’t probably even be around, well, okay. Notice that. Be aware of that.

If the asset that you’re selling is something that transcends you where you’ve built a machine that does not rely on you being at the center day to day, that’s a vastly different asset that you’re selling with a very different buyer pool that you’re probably approaching. I just thought that was really helpful for us as business owners to think about, “What is this thing that I’m actually building? And how am I creating value?”

Jamison West: That’s great.

Russell Benaroya: Yeah, I thought it was cool.

Jamison West: Can I hit just a momentary pause in the–

Russell Benaroya: Oh, yeah. Yeah. We’ll pause you for a second, and we’ll come right back. No problem. Okay, we’re back. And it’s wonderful that life does not stop just because we’re in a podcast. So, great. Awesome.

You’re going to a big conference in a couple of weeks, IT Nation, which is ConnectWise’s industry conference. You’re a bit of a legend, I understand. And you probably have some speaking engagements there. For those that don’t know what ConnectWise is, you’ve certainly explained it. But I’m curious what message you’re hoping to deliver this year at IT Nation in the engagements that you’ve been invited to speak at.

Jamison West: Yeah, absolutely. I’m fortunate enough to speak at a lot of industry events over the course of the year. I’ve been pretty deeply involved in the ConnectWise community. One thing I think that ConnectWise has done extraordinarily well is build community. It’s something a lot of vendors try and fail to do well. It’s been there, in my opinion, from a partner perspective and now a vendor perspective.

To me, that’s been the difference maker in my attempt. I was fortunate to be on their advisory council for 10 years. I’m now an alumni of that. Not there anymore. But I’ve been a speaker at IT Nation for about 12 years. It’s approved. Formerly it was just called IT Nation. Now it’s called Connect because they have IT Nations, and they call that community.

The IT Nation Connect conference is all about thought leadership. Of the three conferences, it’s the one that I’m most focused on because that’s really what we’re out there trying to do. ConnectStrat will be running a series of… We have five speaking engagements.

There is what we call the five P’s. We walk through operational maturity and helping business owners think through these issues: perspective, which is vision, strategy, execution. There’s people, process, we get into all of these details, performance, and how they implement these components into their business.

At the highest level it runs them through the fundamentals of, “How do I get each of these things locked down or a little bit better in my business?” It naturally relieves that anxiety and fear they have about running a more mature, solidified business. We get a tremendous opportunity to share that. I also have the good fortune. We’ve gotten involved with the Evolve peer groups. We actually have a peer group where you must be able to connect to that client to be in that peer group, and so we’re really working with them on our language growth, intention.

Then finally what’s really fun, just a side little anecdote. I was a competitor on something called Pitch IT that they put together. They love to fund small startup software companies. I was invited to be a judge for Pitch IT about three years ago. It was very fun. A great winner, somebody I knew won that competition and got $75,000 from ConnectWise. Writes him a big check and says, “Go.” And it’s untethered. “Go make do.” It’s a wonderful thing that they’re doing to give back to the community.

The next time I went to a conference, I was pitching a new company. We won, and that’s how we funded TimeZest which is one of my software companies, TimeZest. It does calendaring in the IT services space. It’s like Calendly but for the IT services space.

Now I’ve been invited to come back as a judge again. So that’s another thing that I get to do. I’m going to be a busy boy at the conference. It’s like my year culminates usually in that conference. Then I go to sleep for a month, and all of a sudden it’s Christmas.

Russell Benaroya: It’s so nice to have you as part of this industry giving back the way you are, which is awesome. What is one question that people don’t usually ask you? Maybe they’re intimidated or they just figure you have it all figured out. Jamison, what is the question that people don’t usually ask you that you wish they did to share a little bit more about who you are?

Jamison West: I mentioned this. I think this probably comes from my coaching tendency, but I tend to get very transparent very quickly and ask a lot of questions as a coach. I push hard. I’ll ask questions that make people uncomfortable.

What I love is what that usually turns into, not always, is people finally get comfortable to ask me questions that they wouldn’t have otherwise asked me. Because I find when you share from the heart from a depth of light like that and when you’re willing to ask those questions, they usually come back at you.

I love when people ask when I’ve felt fear. You’re right. People have this expectation that I… Part of the reason that I get that transparency is because I need people to know I have made every mistake and continue to make most of them in my life, in my business. For whatever reason, I’ve just put myself out there. People have built this confidence around me, and all of us feel sometimes about the deservingness they have around where they are positioned in life.

I love when people ask me questions around, “What’s the worst fear that you have? Not the past. Where were you at?” People can ask me about my past and things I’ve run into. What about today? I have all kinds of vulnerabilities and questions in my life and in my business and personally, and I’m going through it like this is a journey. There’s no end to it. I’ll never reach where I need to be.

I like when people get intentional about where am I current because as a coach, I need a coach. The most important thing I can have is somebody challenging me, and I don’t think that’s a natural tendency for most of the people I talked to. It’s a natural tendency of mine, but I love it when it comes back and I get challenged.

Russell Benaroya: What is a fear that you have right now?

Jamison West: Wow. I’ll take a business right now that I have which is TimeZest. We have put such incredible efforts for the last two years into this business. But when you build a software company, it could take just one of the big competitors in the space to write the right code. It could take one technical failure on our end.

I feel hyperconfident in all these areas. But I just know that any day that the investment time, energy, and growth that we put into this business it’s always like, “I don’t want to lose that.” That fear is also exactly what allows us, and we work so intentionally in saying, “What are we fearful of? And how do we mitigate that fear?” which is a wonderful thing.

The funny thing is you have to examine. I think sometimes when you get fearful particularly around business or anything it’s like, “How realistic is that fear? Does that come from just you?” and stop all of it.

I don’t broadcast myself as a fearful person. But like everybody, I’ve got a ton of it in there. Everybody does. If you dig deep enough, it’s there. It’s somewhere in there. And it’s a healthy thing. I would say that’s one of my fears is that we make some missteps that I’m not seeing right now, and it costs us this incredible amount of work and great energy that we put into this thing.

Russell Benaroya: Tim Ferriss has a great exercise on fear-setting or I think of it like a pre-mortem. So document the fears today and talk about them and get them out there. What we often find is that fear is a function of a story in your head for a future event that has yet to occur, probably won’t occur. But it’s triggering for you something inside that creates that anxiety that we often feel.

Just liberating yourself by expressing it, being aware that you’re just telling yourself a story about it, and most importantly, the actions that you take are driven by a plan that’s associated with the fear, as you said, that you’re trying to mitigate. It’s a very natural feeling. I appreciate you sharing that, and I think there are some really effective ways to approach it.

Jamison West: Yeah, that’s great. Absolutely. What you just said is not unlike why I wrote the book. You can read it. It will probably speak to anybody who’s ever thought about selling their business, and it’s going to identify some of their fears. It’s also going to walk you through an experience share of how it could come to play out in a way that may resolve some of those anxieties. So that’s great. I love it.

Russell Benaroya: Jamison, we’re excited about The Emotional Side of Selling your Small Business which is coming out when? By the way.

Jamison West: It is out now.

Russell Benaroya: Okay, so on Amazon?

Jamison West: It’s officially on Amazon. Yeah.

Russell Benaroya: Okay, terrific. We’ll put that in the show notes, and thank you for sharing about what you’re doing at ConnectStrat and the impact that you’re making in the industry and the guidance and the mentorship and the structure and the framework and the operating system that you’re trying to bring to business owners to give them more understanding and control of the levers of this thing that they’re building which is designed to free them to lead the life that they want oftentimes becomes a great burden or the shackles that keep them from achieving their dreams. I appreciate you helping them break out. You’re a great friend. I appreciate everything that you’re doing with us. You’re a great counselor, and I can’t wait to see you in Orlando in a couple of weeks.

Jamison West: Perfect. Thank you very much.

Russell Benaroya: Thanks, Jamison. Thanks, everybody. Have a great week. We’ll see you next time on the Stride 2 Freedom podcast. Have a good day. Bye.

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