166: The Power of Community with Jack Wilson
Sales Success StoriesAugust 29, 2023
166
01:10:4897.6 MB

166: The Power of Community with Jack Wilson

In one line

Jack Wilson — a longtime top-performing seller who left Cinch IT, got laid off from a startup, then bet on himself — replaced his full-time base salary in a single day by signing 3 fractional clients from a network he'd been quietly building for years, and argues that community and boundaries, not blind company loyalty, are what actually protect a sales career.

Who is Jack Wilson?

Jack Wilson is a fractional sales consultant, coach, and relationship-management operator who returns to Sales Success Stories nearly five years after his first appearance (episode 57, then VP of Sales at Cinch IT). After helping franchise and scale Cinch IT nationally, a stint as an individual contributor at benefits-marketplace Fringe, and an 8-month run at an early-stage startup, Jack now runs his own business selling into the HR suite of large enterprises on a fractional, retainer-plus-commission basis across financial-wellbeing, wellbeing-SaaS, and cybersecurity verticals. He is one of the most prolific contributors to the Daily Sales Tips podcast (79 tips) and a fixture of the Sales Success Summit community, where he joined Dale Dupree's Sales Rebellion in 2019. He credits three things for his success: Minimal Viable Habits, community, and integrity.

Key questions answered

What does Jack Wilson attribute his sales success to? Per Jack Wilson, on Sales Success Stories, three things: Minimal Viable Habits (a small core group of activities done consistently, at a sustainable pace that doesn't burn you out), community (which he now ranks above "network" because it's something you invest inputs into so the outputs are there when you need them), and integrity (coming from pure, positive intention and treating sales as a noble, problem-solving profession). 0:01:32

How did Jack Wilson go from full-time individual contributor to a fractional sales business? Per Jack Wilson (independent), after being laid off from an 8-month startup role he gave himself a deadline, ran a "W-2 pipeline" of interviews and a "clients" pipeline in parallel, and let the faster answer win. He'd been building the ground for it for years by staying open in conversations, so once he committed he replaced his previous base salary, gained more upside, and works less — consulting for SMB-to-enterprise companies on go-to-market, plus one-to-one and group coaching. 0:08:18

How do you use your network without feeling like you're just asking for favors? Per Jack Wilson, activation isn't linear (build trust, then finally ask) — the order fluxes because the world is dynamic. His signature move: whenever he makes an ask, he asks back "How can I reciprocate?" — and he means it. In roughly six weeks he'd helped 27 sellers find jobs, deliberately banking goodwill before he needed to call it in. 0:30:24

What is a "confluence of interest" and how does Jack Wilson monetize introductions? Per Jack Wilson, instead of fearing a side hustle as a conflict of interest, you engineer a confluence of interest: you're already having discovery conversations with a captive audience (in his case HR leaders in the enterprise), and separately you represent companies whose solutions fix the very problems those buyers describe. Connecting them adds real value, cements trust, and can pay you — he likens it to Hawkeye's quiver, switching arrows to fit the buyer's need. 0:25:32

How should a fractional seller price their work? Per Jack Wilson, avoid pure pay-for-performance and time-for-money models; take a retainer plus a commissionable component, because activating your network is finite and carries real risk you must be made whole for. His framing to clients: "you're not paying for my availability, you're paying for my ability." 0:43:03

Why does Jack Wilson say sellers should stop being loyal to companies? Per Jack Wilson, sellers over-index on loyalty and over-leverage themselves to employers who, when push comes to shove, will always look out for "number one" — not out of malice, but because a business is a business. The fix is to keep outlets open, augment income and network, and lean on community so you're never forced into a reactive, fear-driven job grab. 0:59:31

Frameworks & concepts

  • Minimal Viable Habits — a small, measurable, repeatable core group of daily activities done at a sustainable pace ("your sweet spot") rather than to burnout; wash, rinse, repeat for consistent success.
  • Confluence of interest — Jack's inversion of "conflict of interest": position a side business so the buyers you already talk to and the solutions you carry naturally reinforce each other, adding value on both sides instead of competing with your primary role.
  • The curse of knowledge — because sellers live and breathe sales daily it feels unremarkable, but that same skillset is a superpower to a business that lacks it; coaching serves people who are where you were, not where you are (Jack credits Justin Welsh for the framing).
  • Seller-as-venture-capitalist / luck surface area — treat your work like a VC portfolio of "lottery tickets" (multiple fractional clients), since you only need one to pop; widen your "luck surface area" (a phrase Jack attributes to DeJuan Brown) because "luck is when hard work meets opportunity."
  • Community > network — a network is the surface; community is what you invest inputs into over time so the outputs (support, opportunities, mental health) are there when needed.
  • Stop personifying companies — "culture" is partly internal marketing for retention; loyalty isn't a two-way street, so reconcile a semblance of loyalty with hedging and protecting your own long-term security.
  • Boundaries before you need them — set family/work boundaries proactively, because by the time you need them it's too late to build them; Jack names his non-negotiables to hiring managers in the interview.

Notable claims

  • Per Jack Wilson, after being laid off he brought on 3 clients in effectively one day, more than replacing his base salary with more upside and less work.
  • He contributed 79 of the 1,605 Daily Sales Tips episodes — almost 5% of that show.
  • In the span of "the last month and a half to 2 months" he helped 27 different sellers get a job.
  • Out of layoff fear he ran 21 interviews in his first 2 weeks before choosing the fractional path instead.
  • He told a prospective client who scoped a role at 20 hours/week that he'd deliver better results in about an hour a day, because you cut the forecasting, QBRs, and one-to-ones a company would demand.
  • He cites the stat that the average seller spends under ~30% of their time on actual revenue-generating activity — time a fractional operator can skip entirely.
  • Jack joined Dale Dupree's Sales Rebellion on the spot at his first Summit in 2019.

Companies, tools & books mentioned

Companies & organizations: Cinch IT, Fringe, Deel, Oracle, The Sales Rebellion, Sales Success Summit, Sales Success Community, Daily Sales Tips.
Communities & people referenced: Dale Dupree (Sales Rebellion), DeJuan Brown, David Weiss, Jacquelyn Nicholson, Alex Smith, Luke Floyd (Deel), Justin Welsh, Jeff Bajorek.
Concepts & analogies: Minimal Viable Habits, confluence of interest, curse of knowledge, luck surface area, ikigai, Hawkeye/Marvel quiver, "pack your chute before you get on the plane."
Connect with Jack Wilson: LinkedIn. His first appearance is episode 57.

Quotes

"I think the people who boast about work-life integration, those that say, hey, I don't need boundaries because I like when work blends in. ... I fear a lot of those people, they just haven't experienced the moment in their life where they need the boundaries." — Jack Wilson 0:20:23
"One of the things I say to almost anyone who I make an ask for ... it's genuine. I always say, how can I reciprocate?" — Jack Wilson 0:30:24
"Sales is like the mob, right? You can never leave. Like once you're in, like you can't get out and it, it drags you back in again." — Jack Wilson 0:43:03
"You're not paying for my availability. You're paying for my ability." — Jack Wilson 0:43:03
"We as sellers and employees have to stop overleveraging ourselves with a company that at the end of the day, when push comes to shove, they're going to look out for number one." — Jack Wilson 0:59:31
"That part of October is now officially blocked off, like in perpetuity." — Jack Wilson, on the Sales Success Summit 1:07:34

Listen & full episode details on top1.fm →

0:00 Scott Ingram: This episode is brought to you thanks to the generous support of Vidyard. To learn more about them and our other fantastic sponsors, click over to top1.fm/sponsors.

0:18 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm.

0:29 Scott Ingram: Here's your host, Scott Ingram. Today, my guest on the Sales Success Stories podcast is Jack Wilson. It's been almost 5 years since my first conversation with Jack in episode 57, and the pivot he's made recently, I think, is super relevant, and I couldn't be more thrilled to be doing this round 2 with someone who has become one of my best friends. Welcome back to the show, Jack.

0:55 Jack Wilson: Welcome, welcome, welcome. I can't believe you just said pivot. Like, one of my rules post-2020 is like I was never gonna say the word pivot again, but you already did it. You opened with it.

1:04 Scott Ingram: I didn't let you… I didn't preview my intro script, which is about the only thing I have scripted. But this is going to be really, really fun. And we talked through this just a little bit. And it's amazing how strong your recall is. Because I didn't think that you would remember all of it. Because where I want to start, where I like to kick off even in round 2, is with that immediate value. And I want to talk about what do you think are the top 3 things that have contributed the most to your success in sales?

1:32 Jack Wilson: Yeah, one of them is still very true today as it was, gosh, I can't believe it's 5 years ago, but that is that everything that you do, it has to be measurable and repeatable. And for me, that translates into what I call minimal viable habits. So understanding that there is a small core group of activities that you have to do consistently on a day-to-day basis, that's gonna lead to success. And I genuinely don't believe that you have to do those in a manner that burns you out. I feel like you have to find your sweet spot. You have to understand what a good amount of effort looks like and what you could do consistently over time. And if you do that, you wash, rinse, repeat, you will have consistent success as well. So I think that's number one. Number 2 is definitely moved up the ranks, if you will, over the years, and that is community. And I might've answered that question differently a couple years ago. I might've said network, but I think network is sort of just scratching the surface of true community. To me, community is a stronger word because it means it's not just something that you look to get out of. It's something that you're consistently putting inputs into so that when you need the outputs, they're there. You've built that investment, that capital. So Having community through networking, through organizations, through close relationships is very important, not just to success from a career perspective, but even like tactically in sales, being able to leverage people in your network to find opportunities and to get in opportunities, but bigger picture in your life, in your career, in supporting your mental health. That's very important. And then The third one, man, I think I'm like struggling to pick a third, but really what always comes to mind is it's integrity. And it's sort of understanding that in order to be successful, probably any walk of life, but more specifically in sales, I feel like you have to come from a place of such pure and positive intention. And you know, when I originally came to the Sales Success Summit the first time, gosh, in 2019, I think it was, I met Dale Dupree. Dupree and I joined the Sales Rebellion on the spot. And I did that because there was a revolution of character in sales. We understood that we wanted to restore sales to the noble profession that we believed it was. I think that's come full circle. I think the bad in sales and the negative stereotypes have started to rear their heads again because technology is allowing people to sort of rest on their laurels and to get a little lazy. And so I believe if you're going to be successful, you have to elevate yourself. You have to come from a place of high character, high integrity, high ethics. And the intention behind sales is always to do best by your clients, always to be a problem solver, to be strategic. So integrity and ethics means different things to different people, but whatever the positive version of that is for you, if you bring yourself, your whole self to the job every day with positivity and ethics, then I think you will find success.

4:43 Scott Ingram: Man, such good stuff. You know, what's really interesting for me is at this point, like I also have to be thinking about my own presentation at the summit this year because I committed to talking about my defunctification process. It's fascinating how much of that sort of aligns to the things that really helped me break through. And I haven't been thinking about it this way, but the minimum viable habits is actually a great term for one of the key ingredients to what I had to start doing, right? It's probably a little bit different lens than the way that you and I have talked about it before in terms… because it was more of like a prospecting pipeline, you know, focused kind of thing. For me, it's more of like a mental health routine. Like if I'm doing these things, then a lot of other things automatically fall into place. Right. And community as well. That's probably my biggest superpower in breaking through. Like I tried, you know, talking to professionals, but they could not get me the way that other top performers can understand me. And so like being able to lean into the community and people like you, like very, very, like specifically you to help me get through my stuff was huge. Absolutely huge. So really good set of stuff. And it's so interesting how the full circle thing it does, it all comes back around.

6:06 Jack Wilson: Yeah. And it's funny when you say that, like, I guess in sales, we're all part broken people and there's nothing better than having a bunch of broken people around you who were broke because the same reasons to help you get through it. So, but I mean, I think even you and I's conversation, cuz I remember it like yesterday, you know, one of the things we talked about to get out of that rut was, you know, what is the one thing that if you do it every day, you knew you had a productive day? And I think for us, we're very unique in that it was have a conversation with somebody that just genuinely lights a passion in us that can translate in many different ways, right? It could be talking to somebody in your network. About, you know, maybe you're looking for a job transition and someone else is going through the same thing, or they've just been through it and you're kindred spirits. Maybe it's just someone out there trying to, you know, book top of pipeline stuff, suffering through it. And, you know, you just want to have somebody that you can kind of reconcile those things with. So community is more important for many different reasons, not just getting things done, but just helping you be whole as a human being.

7:12 Scott Ingram: Yeah. Well, I know that community is going to be a theme, and the first thing I want to do is just kind of get caught up. So when we talked 5 years ago, you had come out of a successful career as a top performer in kind of the banking space. You went to work for Cinch IT, and when we talked, you were leading the sales function and building a team for them. I know that role evolved and kind of the direction with Cinch IT evolved, and then other things have happened. So kind of walk us through that journey, get us up to speed. Before Jack gets us current, let me give a quick shout out to our friends at Vidyard who do so much to support this show and this community. And I hope you'll help me return the favor. If you'll go to top1.fm/v for Vidyard, you can download their free plugin and start creating authentic videos that you can incorporate into any part of your sales process, from starting new conversations to walking through and reiterating the most important impacts of your final proposal. Top1.fm/v. And now back to Jack.

8:18 Jack Wilson: Yeah, I feel like I need a leather couch now to do this. So yeah, like when we talked, we had just started to scale Cinch IT. We had hired, you know, a handful of sellers. We were growing a team. We were going from really, you know, a small niche regional shop to really what would become a national player. We ended up franchising and, you know, the franchise today, they have over a dozen locations all across the country. And after we had launched the franchise model and we had started to grow, you know, 2019 and 2020 happened, which changed sort of a lot of the trajectory of that business and especially the forecast of how fast and how soon we would grow. So we sort of started winding down like the aggressive growth plan, which I wasn't there to grow slow. I was there to grow fast. And when there's a mismatch, you've gotta understand it. And I think, you know, Both myself and, you know, the leadership at Cinch IT saw that and we sort of had a mutual agreement to exit. And it was interesting to me cuz at that time, like that was supposed to be like the mic drop in my career, right? You go through a long career in sales, you're a top performer, you finally dabble in leadership, you find out that you're great at leadership, you jump into an organizational leadership role, you find success. Like now it's time to hang up the laces. Like we did it, right? Like mic drop. Well, I broke the rule of mic drop and I picked the mic back up. And it was like, well, now how about an encore, right? What are we gonna do next? And at the time I had just had my first son, Jackson, who's now 2 and a half years old. And it was a real decision, you know, do I actually go back and get a, you can't see the air quotes, but like, do I get a job or do I sort of venture out on my own? Do I take this capital that I've built? Do I, you know, cash in on the network and some of like the goodwill that I have to actually branch out on my own? At that time I decided I'm gonna do the interview game and I'm gonna find a couple of roles that I thought were exciting and interesting. And at the same time, I was gonna try to test the market to see if I could get some clients for myself. And what happened was sort of like a race to the answer, and the answer would let itself be known. You know, I got passed on one opportunity that I really, really wanted. I was, I came in second place, which as a seller I can't stand because I don't like to lose as much as I like to win. I do not like to lose. So I came in second and I said, you know what? This is for the birds. I already have 2 clients lined up. I'm just gonna go for it. So I actually decided to go out on my own. Going out on my own meant consulting for SMBs and mid-sized companies that were really trying to scale their sales org. So to do what I just had done for Cinch IT for other businesses trying to cross that chasm, I also did one-to-one sales coaching and group sales coaching for individual contributors. And I was able to cobble together enough opportunity to actually give myself a raise from my previous career. So I did that. I committed to it. I was doing that for 6 months, which is a pretty short amount of time. I loved it. I had a lot of control over my life. I didn't work Wednesdays so I could just be with my son, give my wife some time to focus on her career. Everything was great. Then some guy from the Sales Success Community called me out of the blue. And said, hey, come work for me. I want you to be an individual contributor. I'm gonna go be a leader at this enterprise SaaS company. And it got to a point where the decision was out of fear, to be honest, if I'm being really authentic. When you run your own business and you're an entrepreneur, you're thinking, where does the next client come from? And it's far different from what happens if I don't hit quota, because when it's somebody else's quota and it's somebody else's rules and they're cutting you a check, you don't feel as though the risk fully falls on your shoulders. So, you know, when that offer came, I thought about it. I said, you know what, I've done this for a while, but I'm gonna go do what I thought, in my opinion, was the more secure route. And I actually consciously decided to go back and be an individual contributor because with a new family, the amount of time it would take to be a leader, I didn't feel I had that kind of time and commitment to give. I wondered if I still had the fire. To be an individual contributor, cuz it takes that motivation. It takes that fuel to really like get up and go and get after it. But I wanted to find out, I said, you know what, let me test myself. Let's see if I still have the fire. I took the opportunity, turned out I did have the fire. I did get up. I was really passionate about it. I loved the company. I loved what the product was until, you know, I found out some other things about the leadership culture there, which is a longer story for a different day. Or if you join us at the summit, we could talk about that over a couple drinks. But I actually got kicked in the teeth in that role. I didn't do well. I really struggled, which was tough for me because as a top-selling, top performer my entire career, like you really have an identity crisis when you're struggling. And it was interesting because I was doing really great work. I was doing some of the best work, working harder than I had ever done before, opening up a lot of really good opportunities, but it just wasn't coming through in results. And then, you know, I had another child. That was an accident. Again, another long story for a different day, but we had another son, our son Weston. And another thing that I learned is like, if you're trying to be a top contributor and grow a family, those 2 things don't really go that well hand in hand. I know a lot of people that are being successful in sales while growing their family. My hat is off to them because it is a real challenge on so many different fronts, but you have to be consciously aware. I think when you decide, hey, we're gonna go through this period in our life where we're gonna grow a family, you have to understand what that's gonna mean for your career. And you have to go in eyes open, understanding the risks. So it impacted me a lot. I actually ended up transitioning outta that role. And then, you know, when that transition happened, here we are again at the crossroads. Do I go and take a job? Do I do my own thing? And then at that time, I actually just said, I want to go work for a leader who I believe will make me a better seller, who will give me a different perspective. And I was actually privileged enough to work with DeJuan Brown, also from this community, who his flavor of leadership was very similar to what I believe good leadership looks like. Human-first leadership, full transparency, trust, and truth, supporting someone, you know, in reaching their goals and helping them put their family first. So, I took an opportunity to go again into individual contributor role. And this time was a really small startup, which was a bit of a risky proposition. We had really big ambitious goals for a product that wasn't necessarily proven yet. And that lasted only 8 months. So the reason I tell this long story is because A, I tell long stories, but B, the point is when I had the choice to say, I'll bet on myself. Or I'll take a safe opportunity. What I perceived to be this safe, secure opportunity actually ended up being no more safe or stable than going out on my own because I ended up transitioning through, you know, 2 different jobs in a relatively short period of time anyways. So fast forward all the way to today.

15:33 Scott Ingram: Wait, wait, wait. I'm gonna pause there.

15:35 Jack Wilson: Full stop.

15:36 Scott Ingram: Yeah. So we'll get to that stuff because this next part is really the why that I wanted to have this conversation. I think it's so interesting. And what I'm seeing, and really the reason I wanted to have this conversation is because I'm seeing so much impact in this space, in this community, by folks who are getting laid off or they're just in untenable situations. Like their company that they're working for isn't really viable, whether they're admitting that or not. There's a lot of really challenging things. And so this is something that I wanted to really address. Head on. And, you know, we'll start the conversation here. We are absolutely going to continue this conversation as part of the summit. I mean, Jack, you've been part of many of these conversations and on panels and in at least one iteration every year of the summit. We've had sort of this ongoing conversation about managing your career in sales. And the first couple of years, it was really about, you know, which path do you choose? Do you choose the individual contributor path? Do you choose the leadership path? Do you choose some alternative path, right? Do you go into a different role or down an entrepreneurial path, or do you buy a franchise? I mean, where we've got folks in the community that have done that. And it's evolved more. And really what I think this conversation is, how do you protect yourself, right? Given that even the things that we thought were safe are not safe. How do you make sure that you have outlets? How do you augment your income? How do you augment your network and have, make sure that you have community in place to support you? And then what other paths does that potentially open? So we'll come to that, Jack. One of the other things I want to call out for you specifically though is your commitment to your family. And you've always been a very balanced seller. I'll point people back because it is absolutely worth going down this rabbit hole. And in fact, I started going back down it myself in preparation for this, and I think I'm going to finish, is Go back and listen to the Jack Wilson stuff. So Jack's original interview was episode 57. So here's a hack for anybody that's been on the podcast. If you go to top1.fm/jack-wilson, that works for anybody's name that's been on the podcast, you'll get to their episode. So we'll make another one for today. If you go to jack-wilson2, we'll have the links and I'm going to put everything in there, right? So you've got episode 57. You presented at 2 different summits. So you presented in 2019 on moving your margins and the impact of minimum viable habits. That's also where we got to know ikigai. So that… I've also shared that audio on the podcast, so we'll link all that stuff up. Then you co-presented with David Weiss in 2021 on building a world-class sales team. And that's where one of the highlights from that is we all got to learn that there is an I in team and you're just going to have to listen to it to understand where it is because it is phenomenal. And Jack, I think you said you've got a shirt that you're going to wear to this year's summit with that.

18:49 Jack Wilson: I did turn that entire slide into a t-shirt because I felt like it needed to be memorialized forever.

18:55 Scott Ingram: It totally does. But as you know, I'm very, very scared to ever have you on the stage again because of your… I'm going to call them wardrobe dysfunctions. Like this is beyond malfunction because of the intentionality. So your wardrobe dysfunction makes me very, very nervous because to level it up again would be a whole thing. So again, to get the inside jokes, just go down the rabbit hole, go consume this content because it's freaking awesome. So that's that. Those are kind of the things that I wanted to call out and highlight. And again, coming back to your family and your commitment to family, you know, this is something that I think you and I are a lot on the same wavelength. You probably don't think about it, that it's a really different thing. I was talking with a friend of mine, actually somebody else in the community, and we were talking while I was in the car coming back from having taken my daughter to a dentist appointment. I was taking her to school or something like that. And so we're having this conversation in the car and she picks up on what's happening and she just stops and is like, Scott, You need to know that what you're doing is important. Like, a lot of men don't do this. And again, I think that finding that balance, finding how do I be successful in my professional role but also be successful in the other parts of my life that are as, if not significantly more important, is a bigger part of this picture.

20:23 Jack Wilson: Yeah, and I love how, like, there are definitely some mental I say some, there's a lot of mental health threads that are like weaved throughout this entire conversation. And I think it's important because like, I don't like to be like the hot take guy. Like I really don't like when someone goes on LinkedIn and they're like, this has to stop, or this is the way, but this is a little bit hot take-ish, right? I think the people who boast about work-life integration, those that say, hey, I don't need boundaries because I like when work blends in. I like being able to answer a call here, there, or the other. I fear a lot of those people, they just haven't experienced the moment in their life where they need the boundaries. And the problem with that is, is by the time you need them, now you have to go to work to try to figure out how to establish it. It's a little too late for that. So I would urge the folks that are younger in their career, maybe they haven't started a family yet, to think about what it might look like for you when that time comes. And like, you know, do you want to be sitting at the kitchen table and say, I gotta take this, this is a really important client and walk away? Or do you think it's actually better or even more profound if you're able to say, I don't need to take that call because I could take it tomorrow during work hours. And like the real truth of the matter is if somebody calls me at 6 o'clock tonight and I don't call 'em back till 9 o'clock in the morning tomorrow, there's a very small percentage chance that whatever they were gonna say was going to be or needed to be resolved in that window anyways. So like it takes just putting your life and your work in perspective. And for me, that's always meant just having really strong boundaries to the point where when I interview for roles, I tell the interviewer, the hiring manager, hey, look, there's a few things that I'm just not going to compromise on. Can I share what those are? And a big part of that is family, right? Like if I don't take meetings before 9 o'clock in the morning, I'm lucky that I don't have to because I drop my kids off at daycare. You know, 5 o'clock comes around, I'm not taking a face-to-face meeting. There's a rare chance, right? High profile, super big opportunity. Somebody's global and they don't have any flexibility. I can make arrangements for that, but almost as a rule, I'm shutting down. And for me, it's like hide the cell phone. I've learned it has to go away so that I can focus on my family. And look, just because I prioritize family, I am by no means great at it yet. And it's something that you're always working on. You're always trying to perfect. What does it mean to be a good husband? What does it mean to be a good father? What does it even mean to be a good friend? And you can't work on those things when you're distracted and, and you're pulled in different directions. So if they're meaningful to you, dedicate the time just like you would dedicate the time to anything within your craft. That's sort of how I've positioned those things in my life to at least understand that I've got them where they belong, so to speak.

23:24 Scott Ingram: Love it. Love it.

23:24 Jack Wilson: Love it.

23:25 Scott Ingram: And Jack, one more thing. I'm gonna dig the Jack Wilson rabbit hole just a little bit deeper. This is eye-opening, probably for both of us, because I just did this in real time while you were talking, which is very rude. I looked at the number of contributions you made to the Daily Sales Tips podcast. So, in terms of being a contributor, you have contributed 79 Daily Sales Tips of the 1,605. Almost 5% of that show is you. And my assistant is going to hate me for now mentioning this, but if you go to this episode's page, we're going to link every one of those up because there's… what's cool about your tips is in some ways they are a little bit hot take-ish because there's context and themes kind of running behind the scenes that is inspiring these tips over time.

24:15 Jack Wilson: Yeah, and I think what's great about the way I approached contributing tips is rather than it being sort of like, hey, been there, done that, now it's time to write the book, I want to take tips that are things that are contemporary, like, hey, I just experienced this, I took the time to reflect on it after experiencing it, and now let's share it right away in a way that's meaningful with the right context. So yeah, I think you'll definitely see, I believe that, you know, focusing on your personal mentality and your mindset and time management and your focus on your passion and your beliefs are almost just as, if not more important than actual like tangible sales tactics and techniques. And you know, if you're good at one and not the other, you could still be okay. But if you're well-rounded in both, you're really going to be successful and happy. So that was my goal in, in contributing all those tips is I don't want… I just don't want people to be out here, you know, being top producers. That's one thing. I hope people could be successful and happy and find real meaning and purpose and passion in life. And that's kind of my ikigai, if you will, sharing that with people.

25:23 Scott Ingram: Love it, love it, love it. All right, let's get to the meat. So talk about this most recent transition. What are you doing now and why this particular path?

25:32 Jack Wilson: Yeah, it's really cool and interesting for a lot of sellers, I think, because They know it's a possibility, but they don't quite know how to broach it. So what I'm doing now is, well, first of all, let's start at the beginning. I was laid off as were probably millions of people, specifically sellers after only about an 8-month stint with a company. And so when I was laid off, I actually had already entered into an agreement with one client. Now, what I do for that particular client is really just contract relationship management is what I would call it. I have extensive experience selling into the HR suite in large enterprises, specifically talking about benefits and employee wellbeing. And I happen to network with a company that focuses on financial wellbeing. That's also looking to gain an audience with the HR suite in the enterprise-sized clients. So there's a natural fit to say, You've had those conversations. You have a warm network. You also have a proclivity to open up those doors cold. Would you be willing to do that for us in a fractional sense? So for that client, basically the way I've positioned my business is I always take a retainer and then there's some sort of commissionable aspect as well. So what I do is open doors, which is interesting because I think some people are like, well, isn't that like a glorified BDR? You know, it could be if I wanted to make cold calls all day, but luckily I've been in sales long enough. And I have a large enough book of contacts and a network and a community that I can leverage to open those doors. So it's not necessarily just cold prospecting or opening doors. But what I decided once I got that one contract was to say, how can I create what I call confluence of interest? I think one of the people's biggest fears about, you know, side hustles as they're called, is that their primary job or company, if they have one, is not gonna be happy with it. And there are, you know, actual guidelines around what is a conflict of interest and that you can't have these conflicts of interest. But as long as you're not selling against your company, as long as you're not quote unquote wasting the company dime or time pursuing some of these careers, you can create what I call a confluence of interest. So if I happen to be speaking to the same type of people, all I'm doing as a seller is uncovering the challenges that they're facing day to day. How many sellers Have you heard say, hey, if I don't have the answer for my client, but I know the person who does, and I can connect to them, that makes me valuable as a seller. That cements my relationship with them. That builds that trust. So just do that as a business. So on the one hand, you are having conversations with a captive audience, one that you have a penchant to be in front of. In my case, it's HR on the enterprise level. And then on the other hand, you're working with different companies that have different solutions that solve the problems you hear your customer talk about all of the time. I'm a huge Marvel nerd. If anyone knows me, it's not a surprise. So like my analogy here will get lost on some people, but it reminds me of the character Hawkeye. You know, he shoots arrows, but if you look at his quiver, every arrow in the quiver has a different ability. You know, one's explosive, one has a tow cable, you know, one blows smoke. If I'm a seller and I walk into the office of my client and I have the ability to switch arrows to best fit the need that they have, my skill as a seller is just understanding their world, strategically being able to position them to solve those challenges and understand where they're trying to go. What are the goals that they're trying to achieve? And if I can connect them with those solutions and it happens to be through me, and there happens to be a monetary benefit to me because of that, what better confluence of interest is there?

29:26 Scott Ingram: So good. And you know, one of the things that I'm realizing, I think there's 2 sides of this. So this is the first side and I'll try and call out the second side when we get there. But one is coming back to your theme of integrity. If you have sold with integrity over the course of your career, you have accumulated a mass of trusting relationships, right? You have sold to people and delivered solutions and delivered value. And a lot of those people, especially if you go back to the last interview and my conversation with Blair, those people, many of them have become friends over time, or at the very least, they're people that you can reach back to who are going to have good memories and remember the good experiences. And just the ability to sort of tap back into that with additional value, with, you know, here's another solution or somebody that I can connect you with in a way that you can monetize, is huge.

30:24 Jack Wilson: Yeah. And I think one of the other parts of that too is there's a lot of people that spend a ton of effort and energy building those networks But then they're reticent to activate the network. And it's out of a good reason, to be honest. It's because they feel sort of like guilty if you were right. I don't want to go ask somebody for something, you know, if I haven't done anything for them. Some people are just hesitant when it comes to close personal relationships, but just like one of the great characteristics of any good seller is asking for the business. You have to be comfortable asking your network for something that you need. Because it's not a linear path, right? It's not, I find someone, I get to know them, I establish trust, I give them value, I wait, and then I ask because I need something. That's just like this linear traditional thinking of how like a network works. But in reality, sometimes I'm gonna need something today right away, and they're gonna need something down the road. But the order of those things fluxes because the world we live in is just dynamic. So if you have an ask today, Just understand if you came in early with the ask, cool. I'm gonna have to make good on that promise. I'm gonna have to make sure that because I came with the ask and they honored it, I reciprocate. One of the things I say to almost anyone who I make an ask for, and I think they think it's like this like standard email signature sign-off, but it's genuine. I always say, how can I reciprocate? And it's meaningful because if anyone has a specific need that they have, the first thing I'm gonna do is to go about finding a way that I can leverage my experiences, my network, or even sort of add it to the trigger Rolodex of if I hear about something in the short term that I can then connect them back. You know, in the last month and a half to 2 months, I've helped 27 different sellers get a job. I knew that I was gonna have to be the one to ask for those favors one day, but if I just went out and I helped people find jobs, I helped the people looking to land people in jobs that when it came time for me to make the ask, I was gonna be more comfortable doing that. So there is the whole, you know, dig the well before you need it, but it also goes both ways. It's maybe just show up to the well and understand that you're gonna have to dump some water into it after you've taken a little bit out. It goes both ways.

32:44 Scott Ingram: I think there's also a huge context shift that you can make in this too, right? Because if you have vetted a solution, right? If you're going back to somebody in your network and you're making an introduction, if you're doing this right, if you're doing this out of integrity, if you're doing this with the right intent, you're not asking them, you're not taking from them, you're giving to them again. Because if you've done this correctly, I'm helping the company that I'm introducing, right, to this person. The only reason I would ever do that is if that solution or if that company is going to be then helpful to them and is going to add value for them. Otherwise, I should not be doing it in the first place. And so now the game's completely changed, right? There's… I'm never taking, I'm only giving.

33:34 Jack Wilson: And only giving with like real thorough context around what they actually need and understanding where they're trying to go. I think one of the best parts about being a strategic seller is like, once you do homework, this is especially like in the enterprise because they give you the answers to the test. It's all publicly available information. But like once you've done your deep dive on a company, like what they need and the general tenor of what they're trying to accomplish and like the top executive initiatives, those are known and those usually last for a bit of time. Obviously they don't last for years and years, but there is a particular window that you just know, hey, this company is struggling with XYZ. There are 5 to 6 different initiatives that they're going to need, some of which unrelated. But if you have connections in those fields, you can solve those problems. I think a real tangible example of this is when I was selling at Fringe. Fringe is an employee benefits marketplace. So I'm selling it to total rewards teams in the HR suite. I happened to be working with a cybersecurity company that said, Yeah, we need to do this, but also on the docket is we're growing globally really fast. You know, I reached out to people that I knew at companies like Deel, like Luke Floyd and others to say, hey, are you in talks with this company? Because they need a global EOR. If I could help them solve that problem faster by making connection, it's gonna build goodwill with me. It's gonna clear up sort of that project management priority. So that they could start to focus some time and effort on the initiative that we're trying to push as well. But also it's sort of like building this capital that they're saying, man, this guy Jack keeps getting stuff done for us. And eventually I'm gonna have to make an ask that doesn't fit perfectly. And I get to say, hey, remember all those times I did you a solid? This is one of those ones. I need you to return the favor. Right. It's okay to say that. There's nothing wrong with saying I'm pulling the friend card out, right? Or I'm cashing in my chips.

35:37 Scott Ingram: Yeah, love that. Talk a little bit more about some of the other… so we talked about kind of one client scenario that you've developed. What is the other type of stuff that you're doing?

35:47 Jack Wilson: Yeah, so I think the really unique thing is I am actually in multiple verticals and multiple segments. So the one client is in the financial wellbeing space on the enterprise side. Another client is in, I guess you would call it similar, like a wellbeing. It's a SaaS product in the wellbeing space, but they're really selling to like mid-market or commercial accounts. And then I also am actually working with one of the Cinch IT franchises. So we're working in cybersecurity with SMB. So I'm able to kind of spread my experience and talents in the same verticals I've worked in over the years, all at the same time.

36:26 Scott Ingram: Yeah. And I know another element of what you're doing. So we've talked about the one dynamic, which is, you know, the opportunity to be compensated to make introductions and create opportunities and do this kind of work. The other side is the consulting or fractional type of work, right? Where it's not just your own effort. Maybe you're helping them put systems in place. You're helping them build a team. You're helping them, you know, develop their go-to-market. Model, you know, whatever that is. And something that I think this is such a big, like, curse of knowledge thing is all we do day in and day out is we live, breathe, sleep sales. And that's what we think about. And it doesn't feel very special. But when you have that skill set, when you understand how to do all of these things, and especially if you can do it for a business or a group that doesn't have this skillset, it is absolutely a superpower and has so much value. It's not even funny. Right. So can you maybe add some color to that side of things also? Because I, again, I think there are 2 different plays and 2 different ways that we can think about, you know, this is a way that I can augment my income and develop a little bit of a side hustle and I can contribute to my community and grow my network in a really valuable way. But it's also a way that you can hone your own thinking and really make super meaningful contributions to people that are at just different stages in their evolution.

37:59 Jack Wilson: Yeah, and I'm glad you followed up because immediately after answering that, I realized it was kind of like those websites that you read that you're like, those are all nice words, but I still don't get what he's actually doing. So I appreciate that. So to your point, one of the best pieces of advice I ever heard was actually from Justin Welsh on LinkedIn. When he talked about like, you know, starting a following to be able to sell like coaching, for example, he tells people that if you think about where you were a couple years ago, let's say where you as a seller were 5 years ago, and think about the knowledge you didn't have and think about the knowledge that you have today, the coaching and the guidance that you're giving is for people who were where you were. Not where you are. So the curse of knowledge, you're thinking it's common knowledge, but sure, it's for your peers. It's for everyone who's generally in the same place, but there's a whole generation of sellers coming up behind you or people jumping into there that don't have those skills, don't have those experiences. That same general principle applies to the evolution of a business. So when I say I'm helping small businesses, for example, one of them I'm very literally just prospecting into a market. So they wanna open up a particular market. I'm literally doing cold calls and creating sequences and doing strategic outreach. For another company, I'm just closing deals. So they're sourcing all the deals. They want someone to be able to walk through discovery, make the pitch, close the deal. And then for another company, I'm actually consulting with what does that process even look like? What are the tools you should use? What are the things you should be coaching sellers? Should you even be hiring them yet? So it's more of sort of like a fractional strategy role. So you can take the skills that you have and I would say sort of prioritize them. What am I really good at? What am I efficient at? And what do I love to do? And you could go seek opportunities to sort of fill each of those cups. So I don't love cold calling and prospecting, but for some reason I'm good at it and I don't hate it enough not to want to do it every day. And one of the unique things is once you've been successful, there's a principle where we know, I think the number is like under 30%, but like the average seller spends around or less than a third of their time on actual revenue generating opportunities. Well, here's the cool thing. When you run your own business, you don't have to do any of the fluff crap that a company would ask you to. I don't have to forecast. I don't have to sit in and do a QBR. I don't have to do a one-to-one, you know, with my boss. If my goal is to book meetings, I'm just gonna go book meetings and I'm getting paid just to do that. I'm gonna find the way that I know is the most successful and I'm gonna do it on my time. So I've actually had, you know, prospective clients say, hey, we think this is a 20-hour, you know, a week kind of commitment. And they'll sort of set their price based on that. I turn around and say, I'm gonna do that in an hour a day. And I will still have better results than if they brought somebody in full-time sitting in front of a desk for 20 hours. So think about the things that you could do with high efficiency, things that you do very effectively and things that you don't hate, and then turn around and offer those to companies. That don't have those functions fully fleshed out yet. Maybe they don't have a full sales team, they don't have a VP of sales yet, and they need someone's help in actually executing on that.

41:32 Scott Ingram: And let me put a really fine point on that because I think the trap is time for money is just a horrible, horrible model. Everybody kind of loses, right? If you think about it, I mean, I experienced this. My very first business was an IT consulting business. And for those that don't know the story, if you know Breaking Bad, The name of my first company was Gray Matter Technologies. And one of the things I realized very early in running that business was the hourly model was just completely messed up. Because if I'm really efficient, or my team is really efficient, and we can get the same result in a third the amount of time as our competitor, they make more money. Even though they're worse. They get paid more to be bad. And so I think the other thing that is incredibly valuable is, and I'm a huge fan of pay for performance. Like, look, let me de-risk this for you entirely. You don't pay unless you get results, right? But Jack, to your point, there is some upfront work. I think it is important. There needs to be some type of a retainer, some type of skin in the game. I'm not suggesting that people put themselves into commission-only type opportunities. That's not what I'm suggesting. But what I am suggesting is you really have to put together kind of a value-based pricing type of a model that should have nothing to do with the amount of time that it takes you, because if you're good, it's not actually going to take you very much time at all.

43:03 Jack Wilson: Yeah. And I like that you clarified that in the end, because I think the trap is for people to say it's performance-based. Like, if I do this, I get X, And that's actually something I personally wanted to move away from. Part of the reason people want to, you know, look, sales is like the mob, right? You can never leave. Like once you're in, like you can't get out and it, it drags you back in again. And my last career decision was like, I just don't want to have this quota hanging over my head because no matter how well you try to wrap your head around it, even the best years that you have that you're crushing quota, it is this soul-crushing feeling. So what I've done with my business is I will tell a client, I'm not gonna guarantee you any results. You tell me what you're trying to achieve. I'm gonna tell you how I'm gonna go about doing it and how much I'm gonna charge you. And then we're gonna make sure that in that contract, you have periods to kind of look in and say, hey, like we haven't gotten enough, or we have, we're gonna continue, or we're not. Just like any sale, right? Both parties wanna mitigate their risk. The reason I think a retainer is important, you know, one of my first clients, they wanted to do commission only. Well, of course that makes sense for them. They don't have to pay anything unless I've generated revenue. But the way I put it to them and the way I think sellers should think about this, I talked about activating your network and not being hesitant to make the ask. Just because you're not hesitant, you can't make that ask every day and you can't make it often. There's a handful of times that you can go to one single person, for example, people and say, hey, I need this from you. So if you're doing that as part of your service, that's where your value is and that's where your risk is. So, you know, hey, Mr. Customer, if you're asking me to connect you with my network, if I connect you and it doesn't convert to a sale because not everyone is qualified, well, I just sort of burned that one opportunity with my connection for a while. There's value there. You need to pay for that and to make me whole for that. And companies really understand that and they're willing to pay a reasonable amount, especially on a fractional basis to say, okay, put your name out there, cash in the chips for us. And by the way, when it works out, we all win and it's even better. So I would definitely avoid as much as you can pay for performance. I tell people all the time, you're not paying for my availability. You're paying for my ability. And that kind of line starts conversation with people that is really meaningful.

45:36 Scott Ingram: I love that. I love that. I'd also like to… maybe we can both tell our sides of this story because it was fascinating to be a part of the way you executed this. Like, once you decided… because after you got laid off, I knew you were back into that decision point of, well, do I do another W-2 or do I go my own path? We talk through that and just like what the decision point was, what the inflection was, but most importantly, like what the execution was?

46:02 Jack Wilson: Yeah. And it's funny because I actually did it the same way both times I had the choice. So, you know, back 5 years ago when I first had the opportunity, I had fear. It's a real thing being an entrepreneur. And so what I said to myself is I'm gonna give myself a timeframe. I'm gonna start applying for jobs on one path. At the same time, I'm gonna start going to try to see if I can get clients. And at X date, you know, I gave myself, I think, 90 days. I said at the 90-day point, the answer will be known, right? Either I will have an opportunity lined up that I'm in love with that pays the bills, or I will have successfully uncovered that I can get enough clients, or at least have confidence enough that I will get enough to make me whole. So So the first time I did that, you know, I was able to actually get enough clients before landing a job. And the answer was apparent this time. The story you're talking about was really wild because I think you and I had talked about like, I don't even know what I want to do. And so again, fear, I just want to be transparent with people. Fear is real. When I got laid off, my mind immediately went to amygdala hijack. Like I've got 2 kids, I've got a family. We just built a house. Not be one of these people that is laid off for 300+ days. I think a lot of people might know Alex Smith from the community. His story from a couple years ago, I don't know the actual number. I should, cuz we're really good friends, but I'm pretty sure he was unemployed for 400-something days and actively, like in the best way possible, interviewing and doing everything you can as a candidate to stand out. So when I think about these stories, I was like, I, I just can't let that be me. And out of fear, I had 21 interviews in the first 2 weeks. So it was just like, okay, first things first, fill the pipeline, so to speak. But on the other side, getting clients, the reason it came together so fast, it's not because I was doing things to prospect people. It's because I had been doing things all along. To put myself in a position to be able to activate that. And what I mean by that is even if you're in a full-time job today, if people don't know that you are open to the possibility of these things, if they don't know, like if they think you're just head down, super loyal employee, like you don't have any appetite to be an entrepreneur, they're not gonna think of it. But if you're, if you're sort of opening yourself up through conversations, you know, someone has a challenge, you're like, man, I might be able to help you with that? Let's talk about, have you ever thought about maybe someone doing something on the side? Like if you're just entertaining conversations just to see where it goes, it's almost like you're building a pipeline of your own. So when I left Fringe, I had one client that I had met literally on a plane on the way home from a trade show. And I say that because I think a lot of times you hear like influencers talk about, you know, I'm on LinkedIn and I've got X amount of clients just cuz I have a great LinkedIn profile. Like that can work, but sometimes it happens out of dumb luck. But if you've listened to me before, you know, I believe the definition of luck is when hard work meets opportunity. And the opportunity piece of that comes from you availing yourself to it. You know, being gregarious, talking to people on planes, at events, and just sharing what you're passionate about. If people know who you are, what you're good at, what your background is, a lot of times they just ask you if you'd be willing to do things as well. So step 1, put yourself out there, make sure people know that you have these abilities and a willingness maybe to do it someday. But then the other part of that actually came from my network. So we talked about community. I actually had someone just share a LinkedIn post that said, you know, this company's looking for a fractional sales hire. And I did what any good seller did. I would reach out to them cold, send them a LinkedIn message, sent them a personalized video, follow up in a couple days. It was almost like a de facto sequence, book the meeting, have the conversation and, and walk 'em through a process. Every seller knows how to do that. And then the third client happened to be sort of a multi-year conversation that was ongoing. And again, one of those, make sure you keep sort of like fuel on the fire and you keep opportunities alive for when you need them. It was a little ambiguous, but I hope that kind of answers your question. I'm curious to see how you saw that unfold from your perspective.

50:25 Scott Ingram: Yeah. So I'll tell my version and you say what is and isn't true. So the day started, I was on a very long drive. So catching up with some friends and Jack and I were talking and my recollection is you were in this spot of, you're like, because you'd had a bunch of interviews lined up, right? So you had kind of the W-2 pipeline going and you said something to me along the lines of, you know, I think what's going to end up happening is I'm going to take kind of the first thing that comes along because I want to just be in a place. And, you know, it may or may not be the right thing. And, you know, maybe that lasts 6 months, I don't know. And maybe I'll have… I'll use some additional bandwidth to kind of keep going with this process and really try and find kind of that ideal fit, sort of longer-term thing. Is that about accurate so far?

51:16 Jack Wilson: I think the most important thing I said in there that you didn't say was like, And I hate them all. Like, and that was the real problem is I was willing to take a role that I knew I wouldn't love just because I wanted to trade in for security. And even though you actually said the best thing to me during that, you said, you just called your shot and you know it's gonna come true. Why would you still do it if it's not the outcome that you want?

51:42 Scott Ingram: Yeah. And that was it. I saw that and I was like, man, this is not good. Like, I don't love I don't like at all the situation that you end up in, but it's what's going to happen. And the rest of that was like, Jack, I know you. I know that, you know, you like this diversity. You like, you know, you're super creative. You like a lot of challenges. I know you've done some of this consulting stuff before. I know you, you know, you've, you had the one thing going kind of on the side already. I was like, man, why don't you just lean into that? Why don't you do that? That seems better aligned to where you're at. And I think another really specific piece of the puzzle that I shared and based on another experience. So one of the things we saw happen, I won't share names because we, I don't publicly share this session because it was kind of personal, right? It's one of those, you had to be there things, but somebody prominent in the community walked into the Sales Success Summit last year. It was a Monday. And that morning got laid off. But because they had been consulting prior to that, one of those consulting clients had said, hey, and they'd been having this conversation, they'd been trying to hire this individual. And it was like, no, I got this other thing. I don't need this. I'm perfectly happy with the consulting relationship. Well, the layoff happens. And within that day, it was hours, maybe it was minutes. I mean, it happened so fast, it wasn't even funny. So they come to me at the beginning, they're like, this just happened. Here's the move I'm going to make. And before like lunch, they had signed a contract and gone to work for this client and full-time role leading sales, still in that role. And so my advice to you along those lines, 'cause I knew that you knew this story, was as you're thinking about those consulting clients, maybe one or two of them are companies that would be interested in you going to work for them and/or you might be interested in going to work for them, but you can do the due diligence from the ultimate position. You can do the due diligence from the inside and really get a feel with way less risk of this being your full-time thing. And you went all in on this and it taking you 3 to 6 months to go, oh my gosh, what have I done to myself? And it's so hard to untangle that versus, hey, you're paying me every month and I get to learn the organization and I get to see the value and hey, maybe there's a path here to make this happen. So I'll let you follow up on that and then we'll get to the execution because to me it was epic.

54:15 Jack Wilson: Yeah, you kicked off a bunch of really good like analogies in my mind, right? It's the classic like you have to pack your chute before you get on the plane. That way when you jump out of the plane, there's a chute for you to pull, right? But it makes me think of, it's almost akin to venture capital. We as sellers are actually venture capitalists, but it's not money that we're bringing to the table. It's work and work is money. But what happens is we get to do that work either for one company and, you know, that's, hey, I just bet all my money on one pony. You get to do it for yourself, which could still be sort of all these eggs in one basket where you get to diversify. And one of the things I loved about what you said, where it's, hey, this role could transition to full-time or vice versa, like because you know someone, it could turn into a hustle at some point. To me, those are all kind of lottery tickets, right? If you go to a startup, one of the things that I hate is like people want to get into SaaS so bad because they think, hey, I'm gonna get equity. It's gonna pop. There's gonna be an event. We're gonna make all this money. The percentage of companies that actually have a profitable exit is in the single digits. And even if you're in one of those companies, the payoff for you as an individual contributor is minimal. It's just not going to change your life, but everyone approaches it in a way that they think they're gonna be the one that it's gonna change their life. But what if you instead looked at yourself like a venture company and you said, hey, I've got 4 clients. And they're all lottery tickets, and I only need one of them to pop and to have a good association with them for that to happen. You really can start to spread your value, your work around in a way that gives you more opportunities to get lucky. I don't even know where I just saw this. I think DeJuan Brown might've posted something about increasing your luck surface area, making sure that you're just putting yourself in as many places as possible. And it goes back to luck is when hard work meets opportunity, you're gonna work. You're gonna work no matter where you are, but you can control sort of the breadth and scope of the opportunity.

56:26 Scott Ingram: So interesting. I'll add one other like real-world piece to the kind of exit or acquisition lottery ticket. So I have worked, I've done 2 IPOs and an acquisition by Oracle. One of those was the same company. And I would say in each of those times, each of those was very, very significant events, right? I was working for a company pre-IPO, they went public, or in the, in the case, they went public and then a quarter later got acquired by Oracle. In each of those scenarios, as an individual contributor with kind of the options that I had, it was equivalent to like a medium-sized commission. It was like I closed a meaningful deal, right? That was worth, I don't know, 20% of my number for the year. So, you know, somewhere in that realm, like good, nice, but not life-changing at all. Right. So I think we get really skewed from that perspective of what's possible and how valuable that really is. I think the exercise here, what I really want people to do is just give this some thought, be intentional about this as you're planning your career and thinking about all of these things and buying these lottery tickets. Although I don't love the lottery ticket analogy because your odds of winning the lottery, your odds of losing the lottery are 94% with every ticket you buy. So maybe we'll use a slightly different analogy. I think the VC bet is a little bit better. Is where are you placing those bets, right? What industry is this company in? How is this company positioned in that industry? You know, there's so many dynamics, you know, the maturity of the company. I mean, Grant, yes, I worked for 2 companies that went public, but I was relatively late in those processes, right? I joined on average, I don't know, a year, 18 months before those events happened. Had I joined 5 or 6 years earlier than that, it would have been a different story. But it was a little easier to make those picks. Like I could kind of see how things were going and how things were developing. But this diversification thing I think is super important because it doesn't have to be binary. It doesn't have to be, well, it's either this company or that company and this role or that role. It could be that role and I have these 2 consulting clients or I have this role And I've got, you know, this product that I've built and we're going to talk about the product thing in the summit. I know David Weiss, for one, has some perspectives on that. And from the perspective of having built a product, I think there's a lot, a lot, a lot of good insights here, but the whole thing is just being mindful of it and thinking about it and leaning into your community to help you flush this stuff out. Because Jack, I feel like what we were able to do for each other, what you've done for me a thousand times. Is I know you, I see you, I see the options are on the table, and I hope that I'm able to bring some clarifying perspective around, you know, given these options, this feels like you, this feels like the right fit for you, this feels like the best balance of risk versus reward for you in this moment.

59:31 Jack Wilson: Isn't that the best part of community too? You know, and you alluded to it when you were looking for peers to kind of pick you up in a tough spot. You don't have to be in a tough spot to be able to have people that know you and trust you and at varying degrees. And, you know, one of the first things I do when I make a decision is I call everyone under the sun that knows me. You know, I get all of their opinions because all of those opinions are diverse, but then there's like this average sort of consensus that comes out of it. And then that's when you can go, man, the community has spoken. I gotta to that, right? There's real insights. They know me, they've seen me over a longer period of time. Like you said, that's invaluable. There is one thing I wanna touch on too, and this sounds like a little like dark, right? And I think some people are gonna think I'm, maybe I'm jaded because I've gone through some negative transitions, but we as sellers specifically, and I think employees of companies in general, but specifically sales, we have to stop personifying companies. You need to understand that like the word culture, it was actually created for internal marketing purposes, for retention purposes. If we can tout culture, if we can create this mysterious culture, it will help us hang on to people longer. Well, that is not a two-way street. And no matter how positive the culture of a company, no matter how much they put people first, people won't actually ever come first because it's a business. And that's not even saying it. Negatively. I actually don't mean that negatively at all. It's just a function of a business. If there's not enough revenue to cover the bodies, they just don't have a choice. So we as sellers and employees have to stop overleveraging ourselves with a company that at the end of the day, when push comes to shove, they're going to look out for number one. But we as employees are not doing that enough for ourselves. And I believe there is a way to do that. That you're able to reconcile a semblance of loyalty, but also hedge and protect yourself over long-term security. There is a sweet spot to be in the middle of both, but blind loyalty to a company and not blind loyalty, but even I would say over-indexed loyalty can be really detrimental to your career because then you end up in these reactive states like me where I'm thinking I'm just gonna take the next job because I need it, because I need the security for me to feel safe versus proactively contemplating what is it that I want to do? Where are my skills best served? One of the best ways to get into a mindset to do that is to detach from this loyalty to a company that in the end, unfortunately, a lot of them, they're gonna do the decision that they have to make that benefits them best. Yeah.

1:02:20 Scott Ingram: Yeah. There just is no safe anymore. I had a conversation yesterday. This is actually a pending intro, maybe a future Interview here on the show, and they said, "Hey, you know I used to work with this company. They had a leadership change. I'm still in touch with a lot of people. I want to put you in touch with their top seller." And they were the number one seller the last four years in a row. Year to date, 130% of their annual number, whereas the rest of the team was like 40%, and they let them go. And I have some theories, and they had some theories about why that is. And I'm not gonna speculate and get into all of that. But it just goes to show, like you would think. If you're that person, you're like, I'm 3 times, nearly 4 times better than anybody else here. I have the most consistent track record. Still doesn't mean anything. You're still at risk, right? So I think you just have to be completely eyes wide open with this stuff. And, you know, at the end of the day, to your point about the loyalty, look out for number one, right? Like, I believe in loyalty. I think that there is value in that for sure. I mean, heck, I've been working with the same company for the last 7 and a half years. So that absolutely has meaning, but gosh, there's so little that's safe. Jack, the last element of the story I wanted to touch on again was your execution piece. So we have this conversation in the morning where I kind of called you out and said, hey, this doesn't feel right. I think this path makes more sense for you. You text me later that day and you start teasing stuff. And I'm thinking, I think I know what just happened to the point where when we talk the next morning, you had brought on 3 clients, had more than replaced your base salary, have more upside, and will likely work less than in your previous full-time job. Is that an accurate summation?

1:04:09 Jack Wilson: Yeah, I mean, you nailed it. And like, I actually told most of them that I wanted to wait until September 1st to start because I was like, I'm gonna take some time. And then I sat on my front porch for 2 hours one day and realized that I was going gonna lose my mind. So I've actually started work for all of them like early. But you know, to that point, it's, that's got nothing to do with, it's got a little bit to do with me and having a bias for action. But at the end of the day, what it is, is when you make a decision, just go because you can't sit in this place of doubt the entire time. Because look, we're humans, we make decisions out of emotion and then whatever that is, we back it up with logic. So what I always try to do is I try to look from the logical point of view. I make the decision before the emotion can kick in. So if it's logical and it makes sense, go, you've gotta go, you've gotta execute. And that's what I did. And I made the asks and they were all positive and we signed and the rest is history.

1:05:09 Scott Ingram: Yeah. I mean, it's such an amazing story. I mean, I think there are 2 points. You made one of 'em, right? One was just go decide, get in motion before the fear kicks in. Because if you sit there and think about this too long, you're gonna talk yourself out of it. So don't do that. But the second part was that I think is important to call out, you alluded to it earlier, which was it's not like you created these all from scratch within one day, right? These were, you have been contributing, you have been in conversation, you had been creating your luck over a period of time where this pipeline, it was kind of hidden pipeline, but it was there for you to capitalize on. Like once you made that decision, it's like, you know what? I know who to call. I know what to ask. And you did.

1:05:51 Jack Wilson: Yeah. And that's the great part is think about when you're ramping in a new role and there's always like that low-hanging fruit that like you just happen to get because you're new in the role. But once you've got the motions down too, so the fear I had in the past about where does the next contract come from, I don't have that anymore because I realized I haven't even had to turn on a process or a sales motion to proactively go hunt. But as a seller, that's something that it comes natural to me that I am good at. But I was able to be successful without even kicking that in. So just think if you're sitting there today thinking like, I've wanted to do this, I've thought about it, like start the passive stuff first, see what opportunity presents itself. And then imagine what would happen if you actually just kicked in a little bit of effort. And I'm not talking crazy effort, but if you just put forth some consistent daily minimum viable habits to open up some doors for yourself. Your business could… I mean, you could end up taking on more and more clients and actually really, you know, expand your business in a big way. I choose not to do that. Enough is enough for me, and I've decided what enough is, but there is definitely potential for a lot more.

1:07:01 Scott Ingram: Yeah, yeah, such good stuff, Jack. I know we're coming up against a hard stop. Why don't we spend just a minute to talk about the summit and the community and just the importance of this? I know You have been so invested, such a huge contributor. I think that you have benefited pretty significantly as well. Why don't you talk about it rather than me pitching the summit? Why don't you just kind of share your perspective and help those listening make the decision to, you know, pull out their wallets, make the commitment, decide right before you get into fear, decide and come join us this October.

1:07:34 Jack Wilson: Yeah, I'll tell you the first time I attended the summit. I left that event going. That part of October is now officially blocked off, like in perpetuity. It is just, it is a thing. Like my birthday's in February. The Sales Success Summit is in October. It's just something that happens because that's how valuable it was. I actually think one of my favorite parts about the community is many of the people that I have the best relationships with are, you know, those friends that you have. That you haven't talked to in like, I mean, a long time that you kind of start to feel guilty about, but you pick the phone up and it's like you talked yesterday. They don't need to be maintained. They don't make you feel guilty. You just pick right up where you left off. Everybody's happy and valuable, right? There are no less than 20+ people that I have met at the community that are like that. Some of which Jeff Bajorek is one of the the best guys in the community. And I call him like not nearly enough, but from time to time he will call me out of the blue exactly when I need it just to say what's up. You know, Jacquelyn Nicholson is another one of those people. I've worked for David Weiss and DeJuan Brown, who then became friends. And so if you're looking for a place that you don't need expectations going in, but you always know there's something for you coming out, and it is a type of community that you can decide how it fits your life best, I would suggest that this is the event that if you go to one time, you're gonna find where you fit in that community.

1:09:11 Scott Ingram: Brilliant. Brilliant. And of course, the link to get involved in this year's summit, top1summit.com, T-O-P, the number 1 summit.com. As always, my job is to continue to level up the experience. I'm super proud to say I asked the question and the first survey question coming out of last year's event was, was this the best sales event you've ever been to? And 91% said yes, which is thrilling, like an unbelievable thing to pull off and also crazy scary because I have to figure out how to make it better this year. But fortunately, I have some pretty amazing thought partners like Jack. We've had some pretty amazing conversations about how we level up again this year and I think it's going to happen. If this resonates, if this topic is of interest, we are going to be digging in pretty hard. And there's some pretty actionable things that I'm leaning into so that we can potentially help you along this path if it's something that you want to take on. So come join us. Jack, as always, thank you for everything you do for me, that you do for this community. I appreciate you as a friend.

1:10:14 Jack Wilson: I wouldn't be here without you and what you've created, Scott. We talk about it all the time. There are so many lives that you have impacted. And you're probably the worst accepting compliments. So thank you, Scott, for everything that you do and keeping this community strong. Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.