Autonomy is a superpower, with Justin Welsh

Oct 27, 2021


Repeatable Revenue Podcast #006 - with Justin Welsh


In today's show, Ray connects with Justin Welsh to discuss building a team culture of autonomy and ownership. Justin shares how by 27 he had been fired from his first three jobs, and how joining a high-performing, values-centered team shifted his mindset and his relationship to work. A decade later, Justin needed to make another change after finding himself burned out and in poor health, and has since shifted his focus to developing a more intentional life for himself and his family.

Topics Include:

  • Justin's humble career beginnings

  • Mindset shift and maturation

  • Risk vs reward when changing roles

  • The connection between autonomy and creativity

  • Tackle audacious goals without permission–how to move up in the ranks of any company

  • How to create a culture of autonomy as an executive

  • What to look for when hiring

  • Creating a cohesive customer journey

  • What it means to be a hypothesis-driven organization

  • Burning out, creating an intentional life

  • Building a personal brand

  • Seeking feedback as a solopreneur

  • Creating space for creative thinking

  • And other topics...

Resources Mentioned:
Justin Welsh -
Scott Leese -
Jacco van der Kooij -
Jacco van der Kooij -
Starter Story -
Tim Ferriss - 4 Hour Workweek
Daniel Vasallo -
Jack Butcher -
David Perell -
James Clear - Atomic Habits
Amanda Goetz -



RJG: Welcome to the show, Justin.

Justin Welsh: Ray, it's great to be here, man. It's exciting to chat with you hope all is well in your world down in Mexico.

RJG: I have no complaints in Baja, especially this time of year, our winters are nice. Well, I mean, there's a lot of topics, like fun topics that I want to talk to you about today but, we'll talk personal branding, some solo partnership. But I want to, you know, for the audience, I want to set the stage.

And for anyone that kind of doesn't know your background, and do you mind just sharing your path into senior management into sales leadership, like what's the Justin Wells story from sales into the C-suite?

Justin Welsh: Sure, I started in sales in oh three. I graduated from college in oh three and got a job in pharmaceutical sales, which is what my dad did for almost 50 years.

And we had a pretty nice house and a couple of cars so, I thought this had to be the be-all end. I was going to live in Ohio, Cleveland, the rest of my life, and kind of lived the same life as my parents and, the thing that happened is I just wasn't very good at it and so, I got a pharmaceutical job, I got fired, I got a second one, I got fired at my second job and then I had to actually go backward in my career and became an associate at a medical device company, which I ultimately got fired from as well.

So, at 28 I had three firings, no sales, no quota attainment under my belt and, I put a relatively exaggerated resume, which I think all of ours are up on back in 2009.

And I got a call from a company called ZocDoc, which was a nine-person startup in New York City and, they were hiring their second salesperson so, I applied and, I went to the interview, and I was really prepared. I was really good interviewer and not a great employee at that point in time, and I was really prepared for the interview and, I did a good job and, I got the job.

And something really cool happened when I got that job, which was I moved to New York City. So for the very first time as an adult, I'm in this city that has a tremendous amount of energy. I'm working with some of the smartest people I've ever worked with. I'm repping a product that I completely believe in, and I just happen to be maturing at the same time, and the intersection of those four things did something really cool.

And I went on me to say all my very first day and spent the next five years of that company getting promoted multiple times, whole mindset shift for me. So five years at Zoc doc and then after that, I got really poached by a small six-person company called patient pop to be their VP of sales, and so after kind of stinking the joint up for six years as a bad salesperson, I really turned it around and became a different person.

And they took a chance on me and spent almost five years at PatientPop grew the business from its very first dollar of revenue, up to over 50 million in recurring. And in August of 2019, I stepped down and went on my journey of solar partnership and, I've been working for myself for the last 18 months.

RJG: That's awesome. So, when that happened and, they poached you. Were there certain things that you evaluated? So if somebody is thinking about switching and they're on that trajectory, it sounds like you had started to get some wins.

What did you evaluate when you made that change for yourself?

Justin Welsh: It's a risk-reward evaluation. So I'm at ZocDoc there was a different culture there and, it was a culture I loved. But if you looked across the senior leadership team, what you recognized was commonalities that I didn't have. So most of the people in leadership roles were, came from some of those big consulting firms McKinsey, Bain, cause that's where the co-CEOs came from, most of them had an Ivy League degree, Stanford, Harvard a prestigious university.

I'm a public school guy, I've never worked at a big consulting firm so to me, I just saw that and said, I don't think I fit in up amongst those folks.

And when patient pop reached out to me, I thought to myself, here's an opportunity to take a break. To go take my very first executive role in what is the risk? I looked at the price point, I looked at the velocity, I looked at the vertical, they all matched exactly what I had been doing at ZocDoc.

I said, if I'm going to take a risk here, this is the least risky risk of for a first-time executive with the highest upside in potential and, so to me, given the fact that it was so similar to my previous roles, it just made a lot of.

RJG: Makes sense when you were among the evaluations you mentioned culture.

What's a healthy culture for you, or how did you evaluate culture when you were making that switch?

Justin Welsh: Yeah, to me, culture revolves around autonomy and focus. So if you go into an organization and they've got mission, vision, and values that you can re that really speak to you that really get you excited, then you're going to thrive.

You have to have that in a startup. If you don't believe in the mission, the vision, or the values, the opportunity for you to be successful is significantly decreased, and if you look around the folks who are in there, do they all believe in that as well? And are they working autonomously?

Meaning do you have a high-level, high-quality of individual working at the company who can take direction? One time and go out and accomplish things, and when I went and I interviewed with patient pop, what I saw was people often different rooms, just heads down working on projects. There wasn't a lot of meetings.

It was a really autonomous place, and so to me, early on that, spoke to me and, because I believed in the mission of what they were doing, which was really democratizing access to health care providers, it was a no-brainer.

RJG: You have the autonomy and, it actually plays into it. I mean, what you do now, I'm in solopreneur. So autonomy is probably really high up there on your own personal values?

Justin Welsh: Yeah, autonomy is a superpower. Like if you give someone autonomy, their IQ doubles overnight. It's incredible.

Most people, if you micromanage them, will respond in turn, they will want to be micromanaged, they will ask you for everything, they will ask you how to do everything. Give someone autonomy and watch their intelligence double overnight, it's pretty amazing how that happens.

RJG: Interesting, I've never heard that before, I love that. What do you think happens, when you give somebody that freedom and that autonomy to that doubles their IQ?

Justin Welsh: Yeah. I think it puts people into a position where they have to be creative. I'll tell you something there are two different ways to teach people things. You can either teach them step by step, or you can allow them to learn it on their own and I've always been an advocate for the latter.

What the sprinkling of the former. So the way that I think about it is give people enough to self-discover, and as they start to self-discover the answer, they will not only remember it, but they will learn how they self-discovered that to me is a skill in and of itself is allowing yourself to learn things on your own without being handed them.

So to me, when you teach people to be autonomous, when you say, "Hey, here are the outcome that I want you to have now go figure it out, you got to get creative" and, the first time they've figured something out on their own, they're going to want to do it again, and that was the story of my life at Zocdoc.

They gave me all these interesting projects and didn't really tell me how to find the answer, and as I did it, I became known as like the fix-it guy, the guy who like you had a strange problem, you couldn't figure it out, toss it on Justin's plate and, he'll fix it. Talk about a cool skillset to have like a very valuable skillset as you get promoted through the ranks in different companies.

RJG: Yeah, it's funny. You mentioned that as you said that, I thought, I was with the U.S. Chamber for like 16 years, but when I look back at the trajectory and the moves up, it was a lot of "Hey, can you go fix this?" And then senior management getting out of the way and just letting you entrepreneurially or entrepreneurially.

Get the answer, but you own the outcome, so you take a vested interest in that. That's a great point. What do you as you were kind of in your trajectory into, to senior management, I know you have a good network of a lot of sales leaders and managers and salespeople.

If somebody is asking you, "Hey, what can I do to change my trajectory? Like I'm feeling flat and I want to move into the VP rank, or I want to move into the C suite", and what kind of advice do you give somebody to take ownership of their own career trajectory?

Justin Welsh: Tackle audacious goals without permission, so essentially, if you look around in your business, there are a million things that are broken in every startup company, right? Processes, systems, softwares. There are so many things that are broken that I couldn't get to, that my directors couldn't get to that my managers couldn't get to a really great employee who wants to put themselves on a leadership trajectory, looks at a broken situation, and says I'm going to go fix that without asking permission.

And then they go and they fix it. They change the outcome of something in your business and they come back to you or their boss and say, I didn't ask for permission to do this, but I found a way to three X, this or two X this, or decrease the cost of this when employees just take on responsibility like that.

You have an army of autonomous creative solutions oriented professionals. That's when startup businesses, in my opinion, start to grow and thrive, and when I look back at the two businesses, I worked for patient Poppins Zocdoc. They were full of people who were in individual contributor roles, or manager roles who are today CEO's COO's VPs.

It was a farm system of incredible talent and that's because that's the culture that we had in those businesses.

RJG: And if you were, if you're CEO of a startup right now and you want to create that culture are any advice to that owner, to that CEO on how to do that.

Justin Welsh: Yeah. Hire people who can show you some sort of entrepreneurial spirit in their past.

Now, obviously, and I'm painting with a broad brush here, but the younger that you are, the more difficult it will be to show historical entrepreneurship, right. I know that's not necessarily true with some of, you know, Mark Zuckerberg is of the world, but that's not who we're talking about, right. So I'll give you an example.

When I was hiring for my first sales rep in San Francisco at Zocdoc, I came across a guy with very little sales experience, but he had been running a traveling basketball camp that he and his brother put together, and they were also flipping nursing homes and it's like two really interesting entrepreneurial things that didn't relate at all to what I needed him to do.

But I was like, if I hire this guy, I'm pretty sure he's going to figure out how to go make sales and his name was Josh Angeles, he did. He ended up becoming a VP of sales, like I remember, going in and interviewing a young girl who would become an SDR in my organization and, she had created an entrepreneur's club at her college that in and of itself is entrepreneurial.

And the whole topic was obviously focused on entrepreneurship as well so that was helpful. But I just look for little things in people's past, and I would advocate that CEOs do as well that say, autonomy is important to them creation is important to them, because that's going to be really helpful in the early days of your business.

RJG: And do you think there's value in, you talked a little bit earlier about the mission and the vision and the values is that baked into that type of stuff formally or is it just a nature of, this is the way the business runs and it just organically, once you start that avalanche, it just kind of continues it's itself?

Justin Welsh: I think it starts organically, right. So I think it starts intentionally, let me say that. So if I look back at ZocDoc there's two things they did really well. The first thing that they did really well is they had an incredible mission rewind to 2009 way before, everyone was booking restaurant tables online and booking everything they do online, online doctor's appointments.

That was like the first company in that space to do that, to me, I looked at that and said, okay. That's the only way I want to book doctor's appointments moving forward, then they had this incredible founder story of Cyrus, the CEO and founder of the business who ruptured his eardrum when he landed on a plane, couldn't get any healthcare, couldn't get into a primary care doctor.

And those two things together made me feel. Man, I don't want that to happen to anyone else. I want to democratize access to healthcare. So I was really into that mission and, that mission continued at patient pop. And so, I think that part of my success was that I truly believed in those things. And if you looked across the Zocdoc roster or the patient pop roster, everyone bought into that mission.

But more importantly, they bought into those values. So remember, Zoc doc had values, you know, hire better people than yourselves work hard, speak up. I'm sure they have since changed, but people like wore those like a badge of honor, and when you get everyone rallying around the same values, people work the same way.

It's kind of like a cult, but a good one. So I enjoyed that type of environment, if I ever go back to working for someone else, I want it to be in that sort of Kool-Aid drinking mentality. I enjoy that.

RJG: Yeah. And it fosters, I mean, that's where the real teamwork and sets in, you're wearing the same Jersey, you actually give a shit about the other person's results, I mean, your actual collaboration, I guess got on that note.

You have a lot of exposure to not just a couple that you've mentioned but a lot of sales organizations through your network and through others.

What are some of the more common mistakes that you're seeing in sales organizations today?

Justin Welsh: Yeah, I would say two common mistakes is just selecting the wrong go-to-market, often I'll start working with a business in my advisory firm and, they'll have a really low price point product, 99 bucks a month, 150 bucks a month.

And they're going pure outbound and to me and, they're specialized SDRs and AEs, and I'm looking at that same. I don't think these unit economics work very well and often there's a high intent type of buyer and they're missing out completely on inbound marketing or digital demand generation and, so it starts with just having the right go-to-market.

And sometimes the companies I work with don't I think the second thing is measuring the wrong, you know, metrics.

So oftentimes they're measuring meetings scheduled, leads generated things like that, which are, you want to measure them but, they're not the right, measurements if you really want to get the business, right.

You really want to isolate and have a tight funnel, you want to understand how things move from MQL to SQL, to Sal, to win. And you don't just want to know how they move through the funnel conversion rate, you want to know how fast they're going through the funnel and if you're not measuring those things, it becomes really difficult to isolate and fix.

The best organizations can isolate all the different pieces of the customer journey and know trend-wise when things are going well and going poorly. So those are some things that I see companies generally missing.

RJG: A couple of follow-ups on that. So you mentioned the specialization, the SDR and I've seen some good material lately.

In fact, from Scott Leese, he's had a couple of posts on this, that are a little critical of the, like the separated, you know, specialized model versus the holistic sales model. Do you have any opinions on that or is it is a circumstantial?

Justin Welsh: I think it, it depends on a lot of different variables, but I will say this, I've read some of the stuff that Scott writes and, generally the thing that people talk about when they're kind of talking down on that specialized model is why should I have to talk to an SDR? And have this great conversation and then get tossed to another AAE and have this different type of conversation and I see that often, and that is just an outcome of poorly aligned sales people.

So what I try and instill in my sales organizations is something I call one continuous conversation. Meaning if a prospect is talking to an SDR, then they get pushed to an AA and then they buy the product and get moved to implementation and they get implemented in move to customer success.

The conversation that they have with those four different people should feel like they're having a conversation with one person. And that is an outcome of mapping out a really successful, really high touch, really cohesive customer journey. And if you don't do that, then you feel like you're talking to four different people.

So when you have high ticket items, and you want expensive people to be closing business and you want less expensive people to be generating business. I think it makes sense, but you have to have a cohesive customer.

RJG: That's a great answer. Makes a lot of sense. And the other on the second part of that, you had mentioned the funnel and having like a clean, tight funnel all the way through and understanding the right metrics and the velocity of the leads going through.

If you're a CEO and you kind of get that conceptually, but you want to dig in and really evaluate your own sales org. What would you recommend to go learn that to go? I mean, you've gotten it from experience and things like that, but if without that, how would somebody go, kind of self audit or DIY this and look to see if they have the right metrics in place.

Justin Welsh: Yeah. There's a bunch of different ways. I think one way is you get a great book on it. Some of my favorite books are by Jocko Vondra KOOS who does this, winning by design series. I think it's called SAS as a science and, I think those are some of the best books on really taking sales and making it scientific because that's what it is.

And oftentimes product or excuse me, founders are product founders and, so they understand design, they understand science, and so his books do a really good job of breaking that down. The other thing you can do is work with a coach. I coach founders for a living that's part of what I do as my business, bring someone into your organization who has done it before.

That can either be through a coach or that can be through a great executive hire, and so when you make that executive hire in the sales organization, I always recommend that person should be able to carry a bag, they should be able to sell, they should be able to motivate their troops early on all that different thing.

But there should be a science portion to them, and if they can't walk you through the funnel top to bottom and bottom, back up to top, right? How they hit quota, how the team hits quota, how you adjust levers, how you do things to reach goals, and they're not a real sales leader yet, and so those are three ways.

Educate yourself through books, hire a coach or an executive, or, get the right person in charge of you team.

RJG: Good advice, yeah. And you get the right person in there with that science mindset, like you said, they're constantly challenging their own biases. Like give me, even if I have opinions, let's set up a funnel in the right KPIs so that I can test it.

I want to test my own hypothesis and know if I'm from wrong. Let's adjust. Let's pivot as quickly as possible.

Justin Welsh: A hundred percent, we ran a hypothesis driven sales organization at PatientPop. No, even when things were going well, we were asking ourselves what are one or one to two things that we can test to see if we can do it better.

And so me and my team, we're always spinning up one, one experiment after another, just testing things and trying to learn.

RJG: Well, I feel like I could talk sales for hours with you, but I want to get into a couple of other things that are just from following you. And one is I'd love to hear, how do you describe what you're doing today, and in your own words, cause it's a hard intro to make, but how do you describe what you're doing?

Justin Welsh: Yeah, I'm trying to design a more intentional life, right? Like, the first six years of my career really stunk, I wasn't very good at it.

And then the 10 years after that, I figured out what I was good at. And there are two traits that I have as a person that don't work well together. One is, I'm a workaholic. If you put me in front of a computer, I will work for 15 consecutive hours that's just my nature, especially if I enjoy something.

And the second one is that I have a lot of perfectionistic tendencies. And so when you couple, those two things together leads to massive burnout, and that's what happened to me in 2019 and why I stepped down from my role at PatientPop, I just burned out after working really hard nose to the grindstone for a decade.

And so now I am creating a more intentional life in the way that I think about that is I want to be able to do what I want when I want with whom I want. And so what I've done is reduce my expenses, moved from LA to Nashville. I've opened up multiple streams of income through advising consulting, coaching, digital products.

My wife manages our money, so we've cut out adviser fees. We are making one to 2% improvements in all areas of our life to try and live a better way, spend more time together, take more walks, eat lunch together, do all the things that we didn't get to do over the last 10 years of my life.

RJG: So you mentioned the burnout, did you feel that coming, was it a gradual process or was it you hit a wall one day and just felt it knew.

Justin Welsh: No, I felt it coming for a while. I knew in mid 2018 that I was burning out. I was up 40 pounds. I was drinking a tremendous amount to cope with the burnout, eating too much.

Like working too hard, sleeping very little. So I felt that, like I knew that was coming. I think it all culminated in late 2018. I think it was December of 16. I had a huge, like massive panic attack, where 911 had to be called all the EMT has had to come to our house. Like I thought I was dying, be very frank and, that was sort of a wake up call that kind of got me back on the right put.

And as much as I didn't like that day, I'm glad it happened because it's transformed the way that I think about my life and my family.

RJG: If this isn't hopefully not too personal, what was the next day like? So that happens. That's a hell of a wake up call. What do you do the next day? What were the first steps?

Justin Welsh: Yeah, I went and I there's a couple of things. So we committed to walking every day. So we started to walk three miles a day, three times. So we were walking a lot nine miles a day. I started doing intermittent fasting. So making better choices in the morning.

 I cut out alcohol for almost 90 consecutive days. Started reading, taking some CBD, drinking, more tea, doing more relaxing exercises. There was so many different changes that I made the next day because I was scared. I didn't want to have that happen again. And that started to play into where I'm at in my life today and the life I'm trying to design and how we're thinking about life.

It was a really wild wake-up call.

RJG: I can imagine. What are the first steps you'd recommend? So if somebody is in a similar scenario and they're sensing some burnout, there's a, there's obviously a cash and money component, like you can't just quit your job and walk.

I mean, sometimes you can, it just depends. But what advice would you give somebody that's kind of sensing this as building and I mean, are those the steps that you would recommend to somebody else? Or were there certain things that stood out that you would say "here's what the first two, three things I really recommend you do are".

Justin Welsh: Yeah.

The thing that I wish I had done better in that I didn't do was just be really transparent about it to my CEO. Like instead I just bottled it up and decided that, I wouldn't mention it and I'm sure he could see it. I was bloated, my eyes were puffy, I was exhausted, like I'm sure that he could see that.

But I didn't open up about it and I think that had I opened up about it, he may have been helpful. In fact, I know he would have been helpful. And so I would recommend that people talk openly to other folks about it and, then I think it's a mindset shift like for me, I believed at that point in time, thinking back on it, that like I had to do everything.

That everything was in my control and that I could try and do as many things as possible every day. And really it's like burritos principle, right? 80% of what happens in your business comes from 20% of your effort. I wish that I would have instead gone through my calendar in cutout, all the things that I was spending time on that weren't impacting production.

And so those are the two things that I would recommend people do talk to their boss, be open and transparent. If your boss has a negative reaction, you're working for the wrong person and then make some changes in the way that you manage your time and, how you spend your days.

RJG: No, when you say, go through your calendar and cut out everything that isn't working, I sometimes I think I should start doing that right now anyway.

I mean, just proactively the challenge I have when I'm sure others do. The same mindset that put it on the calendar is hard to also differentiate that, because you're looking at well, that one that does affect production and, so you ended up kind of using the same loop that you use to put it on there in the first place.

Have you found an effective way to, to be more objective about those things that are on your mind?

Justin Welsh: Yeah. I mean, what I really have done is, and I'm a systematized person, so this probably won't be that surprising is created a decision matrix, which is really starts off with, will I enjoy this now in my personal life.

Right, and then it moves to like, does this generate income? And if the answer is I will not enjoy this at all, then it never makes my calendar. If the answer is "I will enjoy it, but it doesn't make income, then I have to think through it". If I had said as I, I don't enjoy it and it doesn't make income, it's obviously a no-brainer, but I try and put it through this matrix where essentially I make a couple of decisions.

Yes, no, or outdoor. And so that's how I'm starting to think about my life now. And I would recommend that people in leadership roles do that today anyways, even if they're working for a business, I'm talking to a client yesterday who had a sales leader, expensive sales leader, and he was coaching the team.

Like he should be. It's a smaller organization about six sales employees, but he was also spending his time vetting out a piece of software. Then he was spending his time trying to fix a software issue, working with the developers. And I said to him, based on your hourly rate, I know someone who could do this for half the cost and do it in one day.

And so we outsourced that project and took a tremendous amount of work off of this place and, she gave it to an expert. So I think that when we're entrenched in these situations, we forget that we don't know how to do everything, and so if there's a specialist or an expert who does, and you can pay them a decent fee, go do that, get it done more quickly, allow you to focus on things that are more important and move the project. So I think about it.

RJG: We actually, we're delivering a sales audit yesterday and at the end of this, we're having a conversation with one of the co-founders. And we were talking about this specific support role, which is maybe 40, $50,000 a year, a support role and I said, "well, how much?".

And they were going back and forth on whether they wanted to hire, and I said, well, how much time do you think this would free up? And the co-funders said, I think like 40%, maybe 45% of my time and I thought "Wow" like the price that I would put to get 40 or 50% of my day back. And I don't know the price, but I would, there's a significant amount of your life back.

And then it puts you in that place where you have the head space to be more proactive and, plan and, be more strategic, you know?

Justin Welsh: Yeah. I try and set like an aspirational, hourly rate and, if I look at something and I can outsource it for significantly below that hourly rate, worth it, I could tinker building my personal website for five hours. I'd rather just give it to someone who builds websites.

RJG: I hear you, is the decision matrix? I know you had a couple filters on there. Is that just an informal process? Like a habit you've built into doing things now? Or is there a spreadsheet somewhere that you are a running mate? Anything of importance this matrix?

Justin Welsh: Yeah. It's literally a matrix that I have right here.

RJG: Oh, that's awesome.

Justin Welsh: Yeah. So I actually have it taped on my monitor as you know Ray, I have a decent social media following. And so, I get a lot of messages every day and I'm a people pleaser by nature.

And so when I get messages, I have to have a framework for being able to say no. And I promised myself that in 2021 saying no would be high on my priority list. And so I use a decision matrix, which I borrowed from a book. I didn't create my own, made it easier, right? You just saw one I liked, I was like, that's a good starting point.

I'll tinker with it over time, and then I went onto a website called starter story and they have a great product. That's just 31 templates on how to say no and, so I downloaded those, downloaded the plugin and every time someone asks me to do something that I don't want to do, I just use one of those templates.

And between that and the framework it's, I vastly improved managing my time.

RJG: Do you recall which book it was that you took the matrix that your preference was?

Justin Welsh: Yeah, it's actually just out of the four hour workweek.

RJG: Ah, okay.

Justin Welsh: Yeah. Yeah. I was reading it the other day like every once in a while I thumbed through it, just to put my mind back into an interesting place in thinking through challenges differently.

And it was the first time that I saw it and I was like, oh, I've been looking for this. I've been needing something just like this. So I just literally cut it out of the book with a knife and paste it into my mind.

RJG: That is awesome. Yeah, I love that. It's probably due for a reread for me. Now I've probably number 10, 11 times.

So, great book. You mentioned your, and you, I appreciate your humility, but your social media following, I mean you have a big following and I'm interested your perspective on something that's been a conversation on our forum, on the sales leadership foundations forum, and it's primarily sales executives and the conversation that's happening right now is the personal branding piece.

The personal branding as a concept is obviously growing in popularity. I think it was accelerate when everybody went remote. But there's kind of this anxiety with a lot of sales managers, sales leaders, CEOs that are seeing their people on their team build brands that may not be affiliated with their company.

 And so you've been on both sides of this. I mean, you've helped me with my own LinkedIn stuff, you have your LinkedIn playbooks that you know the personal branding and how to do this. But I'm curious and you've also been in a CRO role, so what's your take if you're leading a team today and you start seeing people on your sales team that are building their own individual followings and it may or may not be directly related to the company sales or company outcomes, what's your reaction to that? If you're in a sales leadership role.

Justin Welsh: Yeah. I mean, I kind of have a pretty straightforward one, rich, which is I believe in outcomes, not hours and, so I'll start by saying a few different things. Number one, when I was working at PatientPop, I don't own my sales people's social media accounts.

They are their own personal social media accounts, I don't know their LinkedIn profile, I don't know their Facebook profile and, I don't own what they do, really at all, obviously, but especially outside of traditional work hours. So if someone's on LinkedIn from 7:30 to 8:45, or from 5:15 to nine o'clock at night big goal that I would have to have to say that I somehow control that to me is I think that's just straight up wrong.

Number one, number two, even if you're using it during work hours, I care about outcomes. So if you're delivering on your target, screwing around on LinkedIn, for lack of a better term or Twitter , during the day. I generally do not have a problem with that, I also believe that because I don't own those social media accounts in no way, shape or form are you obligated to have them be affiliated with the company that you work for? In fact, I take an opposite stance, which is if you build a brand based on the company that you work for, that's, what's going to happen when you get fired. Your X company is not going to come back and help you rebuild your brand.

So you might as well build it for yourself and, if your company wants you to build it for them, then they can pay for the social media account and they can pay for any activity that you do on social media, after hours, that's how I think about it.

RJG: That's really good advice too, and if you were in a say you're in a sales role today, and you start doing that and somebody, your manager or somebody brings it up to you.

Is that a pretty big flag to you from a culture standpoint or anything?

Justin Welsh: No, not really. It's easy for me to say what I just said because I was an executive and it's much easier for me to say, just go out and do your thing and don't worry about your company. So maybe that's not the best advice, but here's what I'd recommend if I were a salesperson, sales manager is be transparent with your boss.

 I actually did that in the beginning of my time at Patientpop. I said, I want to build a brand like, this is something I want to do and, if I'm doing a good job, I hope that you guys support me in that, and they actually did. My CEO, Luke got me onto the SaaStr podcast with Harry Stebbings 20 minute VC podcast.

He helped me get on some pretty big things because I was doing a good job and, so we were making a trade-off. I was performing, he was helping me build my brand, I think setting those expectations was really helpful.

Number one, but number two, read a media company, right? Not to rip Gary V but, your employees are spreading the word, even if it's not talking about your business, it's just getting eyeballs on the name of your business, the products that your business carries. Look at companies like gravy, gong outreach, who are leveraging their employees to create many media companies inside of social media accounts.

I think if you empower your team to do that, you're actually going to get much more bang for your buck. It's not going to be a distraction.

RJG: Do you think? I mean, so those companies are great examples. I think can a company orchestrate that, is that intentional or is that organic?

Justin Welsh: I don't think you can orchestrate it.

So, Gravy appears to have, I wouldn't call it a directive and I won't speak on their behalf because I don't know enough, but they appear to encourage, let's say that their employees to be active on social media. But if I go and I look at Casey and Tara and the different people that work there, they all appear to have their own voice, their own way of saying things, their own style, their own topics.

And so to me, the best way to do it is to allow all of your team to be authentic, right. Obviously you don't want your team saying things that aren't nice or, professional and all that stuff. So you want to make sure that there's some guard rails up. But to me, it's not orchestrated to me it's an authenticity play where everyone is being themselves and, some people will resonate in others.

RJG: Yeah. It's authenticity is key, whether you're doing it for personal branding or even on behalf of the company. I think the thing, some of those companies that are doing it well, it's also, they have leadership kind of showing the way to like leading by example, not necessarily mandating it, but Hey, this is what I do and, this is how it, this is how it benefits the company and me as an individual and, so seeing that example I imagine is helpful for, especially for, at the CEO level.

Justin Welsh: Yeah. I encourage guys like Jesse Getler, Sam Lewis, Derek, Jen Koski, Kevin Dorsey like they all worked for me, I encourage them to go out and build their brands.

And it did this really cool thing at PatientPop where suddenly we had like four to six people that were starting to get some really good traction and, our recruiting picked up and we heard things from high performance recruits that were saying things like, oh, I want to work for Kevin Dorsey. Ah, man, I want to be on Jesse gambler's team.

And so, it was beneficial there was definitely benefit for our business.

RJG: Right. And I'm aware of the company because of, I mean, Zoc doc and some of the others because of the people that are there, like just good branding. You've mentioned, you've said solopreneur, and I think earlier in the show too, and I've heard you talk about being a solo preneur, and I always think that's the epitome of small business ownership because you're the CEO, you're driving the strategy, and then in many cases, driving the tactical execution as well. I have found it's it can lend itself to the digital, you're just not objective necessarily about your own business, it's why outside help, like coaches and consultants sometimes can help.

How do you cultivate that outside looking in into your own operation or, just kind of keep yourself from getting drawn too far into the trees to see the forest.

Justin Welsh: Yeah. I have a net network of trusted peers that I lean on.

My wife obviously has a really good look at my business and she can see when I'm wasting time or when I'm going down a rabbit hole. She's really good at being, it has giving me like an outside perspective, very objectively, but then I have like a small group of peers that I'll share ideas with, I'll share articles that I've written and say like "does this make sense?" Like "is what I'm talking about?" Resonating here, "do you understand it reading through this?" I just did that with my most recent blog post, I sent it to a couple of buddies of mine. They wrote back some really great feedback. So mostly I just cultivate this network of peers.

And because I've been really active on social media, I've been able to grow that network pretty well, where I asked just very directly for direct feedback, and when they give it to me, it helps me make better business choices, it helps me write better, it helps me produce better, and so I also ask my customers, like I carry a nice six to eight customers at a time and every 90 days I'll reach out and say, What's going well, and what's going poorly with our relationship.

And I take a lot of customer feedback into account when I'm changing and molding my business model. And so from my wife, my peers, my customers, I tend to think I get a decent holistic view of what's going on? What's going poorly?

RJG: And the network of trusted peers was that something that did you formalize that with an ask or is it something that as you just develop a relationship and build some trust? It just kind of evolves into that.

Justin Welsh: I've so it's an interesting question. I feel like with everyone's stuck at home and also trying to be more successful with my time management, as we talked about earlier, formalized sort of groups are starting to lose their luster. Joining more slack groups, joining more communities like join these formal things, feels like an obligation.

So instead what I do is I'm trying to do the reverse of what everyone else is doing. So for instance, if I'm making a business decision and I want an objective opinion, rather than set up a meeting with someone and spend 30 minutes of their time or cultivated group inside of a community software application, I just send a quick text message and I'm like, yeah, you have five minutes to look at this.

And I just get ad hoc feedback all the time, less pressure on that person. It's less commitment on that person. It's less commitment for me and, it's the opposite of what everyone's doing right now. And so I like to feel like that gives people an easy way out to give me four minutes worth of feedback, which is not 30 minutes of their time on a zoom call.

RJG: Right. Yep, that makes sense. And in terms of the execution, I've always, I've said this, you know that about your work. It's very from the outside, looking in everything is very intentional, but I just, from conversations with you, I've said, "Hey, I'm guilty of shiny object syndrome", and I've heard you, you say the same thing.

It's the entrepreneurial, distractions, can I kick in? How have you been able to execute? Because from again, outside looking in it's very deliberate, it's very intentional that the latest release I loved the building, the course in public was phenomenal, and the way that was executed, I thought was really creative, really smart.

So I always admired your execution, everything it's very deliberate, from the outside looking in. But I've heard you say just from our conversations, I'm certainly guilty of it.

We kind of joke about the shiny object syndrome. How do you cultivate the discipline on the execution side when you're an entrepreneur at heart and just by nature, chase good ideas.

Justin Welsh: Yeah. Yeah. It's interesting. I get distracted more by what I would call shiny outcomes syndrome. So I'll give you an example of what I mean by that, and then sort of how I think about it. I look at other creators online, who I think are doing a great job. So there's a million creators, I think, are doing a great job and, some of them are doing things much differently than me, like a very common thing as a paid community.

Do I think that I could host a paid community? I do, I think that people would sign up for a paid community. Other people are doing cohort based coaching programs, an eight week coaching program to lead someone to an outcome. Do I think I could do that again? I think I could.

Yeah, and I get really excited when I see those types of ideas and I start to chase those ideas, recognizing that what I'm actually chasing is the outcome of what that person's looking for more money, more dopamine, bigger performer on Twitter, more popular on LinkedIn and, I have to re retrain myself and step back and say, what is the actual outcome that I'm looking for? And the outcome that I'm looking for is not to make more money. It's not to be more popular, is to enjoy my time more.

And so whenever I'm making choices, my business, I say, is this going to free up my time? Is this gonna allow me to work less? Is this going to allow me to spend more time with my wife? Is this going to do all the things that I want to do with an intentional life? Because if I don't think that way I'll get sucked into an ideal where suddenly I'm going to do an eight week coaching program and I get really excited and really into it.

And then I'm like, wait a minute, this is the opposite of what I'm trying to do. I'm trying to spend less time working on things like this. And so for me, it's all about the outcome like, not getting confused with what my outcome is and my outcome is to live a better life, not to be richer or more popular.

RJG: And if you combine that with what you were talking about earlier, the tendency if you're a workaholic with some perfectionist tendencies, add in trying to do 72 things at once, it is absolute recipe for it's like a time bomb.

Justin Welsh: Yeah, man, I try and stick to real simple things that I enjoy, I like to write. So that's basically what I do. I write, if I'm going to build a course, I like to time box it out to 14 or 30 days that I don't spend a year trying to build it. That's just how I'm thinking about things and I'm not competing with anyone, I don't want to be more popular than someone else, I don't want to be richer than someone else. I want to reach goals that I have internally with my life, so that we can live a more relaxed and comfortable life.

RJG: I love that, as as much content as you create, or do you, where do you find the creative spark?

Is it when you're walking? Is it a specific place? Is it random? Where do you tend to find it?

Justin Welsh: It can be random. But there are generally times that are more creative than others walking is one of them, my wife and I go on a now here in Tennessee, we go on a six mile walk each morning from eight 30 to 10.

And so we get a lot of creative ideas, both of us during our walks. And I like get a creative idea in the shower a lot and, I have like a waterproof notepad that's in there and, so if I'm taking a shower and idea pops in my head, I just jot it down on this waterproof notepad. If I see something online that sparks my interest, that I might have an opposite take on or a different take on, I just use things like pocket to save those things.

Reading a book, might come across an idea that I think is interesting and that I want to expand on. And she really thinking about what happened to me each day at the end of the day. What's something that I learned today that I think would be useful to teach people or to share with people.

And so there's all these different places and, one thing that's been really helpful to me, Ray, is I like to share strong opinions, things that I feel pretty strongly about, and so I just keep a list, wrong opinions that I have now, every once in a while I just revisit it. And I look and say, do I have anything extra to add about these opinions that could be helpful to someone.

RJG: And when you do the reflection at the end of the day, is that a, like a formal journaling process or just a thought exercise that you just, as a habit work through?

Justin Welsh: Yeah. It's more of a thought exercise, it's more of like, I'll sit at the end of the day and, then say, "okay, what happened today?" Sometimes nothing interesting happens during the day or, I just don't remember to make a note of it. But if I think about something interesting, I do it as simple is emailing myself. I don't get into notion or Rome research or all these tools like, I'm not a productivity fiend.

I'm an action fiend. But to me, it's just the least barrier to entry for remembering my idea, which is I'll just fire off an email to myself, that's it.

RJG: And going back to what you said about watching some other creators that are doing it differently than others. And you're one of those for me, like when I watched the way that you're doing things it's always a little bit different than what other people are doing. Who are the creators that you tend to follow most? Are there a few that you'd recommend for others that want to see people doing it differently?

Justin Welsh: Yeah. I like a lot of folks on Twitter. I spend so much time on LinkedIn, engaging with my audience that when I'm done, I generally jump over to Twitter and spend time and, I think that guys like Daniel Vassallo do a really great job on Twitter. He's someone who kind of got me thinking about designing my life in a better way.

He was someone whose ideas and takes on life, started to get my mind churning a little bit and, so I want to give him credit for that. I like Jack butcher, he's a graphic designer who breaks down really complex ideas using simple graphic design he's on Twitter, he's excellent. It's got like a hundred thousand followers, great courses. David is a really good writer, he's someone who just writes really effectively and teaches people how to write effectively. I think, especially given his experience, he's an incredibly good writer. I like James clear the author of atomic habits, he's got a great Twitter, Twitter handle and shares a lot of really good advice.

And so those are four people that I tend to. Oh, and I like Amanda Goetz from house of wise, I think she's really good, she's a kind of a entrepreneur selling luxury CBD online and, she transitioned out of like the tech world and to owning her own business and, I think she's got a cool story that she tells. So, yeah, they'll do like five people I like to pay attention.

RJG: And you spend the time and I, you know, I engage on LinkedIn too, so I know how much time I'm on it. And then when you hop over the Twitter, do you tend to, do you, time-box that like, do you know, Hey, at this point, how do you not get sucked into social media all day when you work in social media?

Justin Welsh: Yeah, so I post every morning at 7:15 central on Lincoln. And I've committed to engaging with the audience for an hour, almost exactly. So, if you make a comment at 8:20, you probably won't get a reply because I do it for an hour. I closed my computer screen, then we go on our walk that's my morning routine.

When I come back, I don't have a real rigid sort of structure for using Twitter or LinkedIn. I might revisit my LinkedIn post later in the afternoon, just to comment back to someone who left something thoughtful, but me what it was just like a, it's a break in between client calls, it's looking for unique and interesting information, it's looking to see the folks that I follow, what they've posted that day, but I probably need to do a better job of spending less time on it, I think is a lot of us get sucked into it during COVID.

I think one thing my wife and I are working on is just committing to shutting our computer down at five, and we're not very good at that and, so we're trying to get better at that.

RJG: Yeah. I know sometimes it's easier said than done, I get that.

And so you, this may be the last question here on the, you built this course in public and again, I think it's something that I haven't seen somebody do, to create or doing something that other people aren't and, so I've enjoyed watching it.

What's can you tell, I guess for the listeners, what is the course and then, what are the one or two takeaways from doing that in public?

Justin Welsh: Yeah. The course is called idea audience proof product, and truly just a side hustle, playbook. It's how to ideate, grow your audience, prove your expertise, and then build a digital product that can sell and scale 24/7.

And I decided to build in public because I think that part of the reason that my audience likes my content is that I tend to be pretty transparent. I'm not trying to pretend that I'm smarter or more interesting than I really am. I'm just trying to share what I'm doing on a regular basis and that seems to resonate.

So I thought to myself, a lot of people ask me how to build courses. No, the easiest way to answer that question is to just build it right in front of them and allow them to see all the ups and downs wins and losses, good choices, bad choices, how much money I'm making, how many hours I'm spending and at the end of that journey, they can make a decision.

Do they want to do that themselves? Right? It's not as easy as it looks spent over a hundred, I think I spent 90 to a hundred hours building that course and, it's been a really profitable good course. But I thought that like unveiling, the curtain would do two things, teach them how to do it on their own and be a really good partner for the course.

And then also maybe build a closer relationship with my audience. I think one thing I hate is when creators are really closed off where you can't really access them, they feel like people who are, you don't exist, right. They kind of up on a pedestal and I just don't want to be that person, I'd rather be much more accessible, much more open, when I say no to things now, one thing I feel good about is that I've produced a lot of stuff in the world that you can go and read.

If you have a question for me and I can't spend the time answering it, it's likely been answered somewhere in what I've created and, so I just point people in those directions, knowing that hopefully I've done a good job in answering most of their points.

RJG: And what you ended up with. I mean, is a more loyal following, you have more authentic relationships, you engage your audience, they actually get to know you better, they become more loyal and even bigger fans, the more authentic you are and, it's a virtuous cycle, with your audience.

I appreciate you coming on the show, I appreciate your time and as you know, I'm a fan of the content and, I know that as a person you're authentic and, so I'm glad to have you on and appreciate your time.

Where can people find you?

Justin Welsh: Yeah. People can find me in a couple of different places. If they're interested in what I'm writing and creating, they can go to that's just W E L S, Justin Wells or, if they're in, an early stage SAS founder, and they want to work with me as an advisor or a coach, they can go to

RJG: Excellent. We'll send them that way and, thanks for your time again.

Justin Welsh: Ray, good to see you as always, man. Thanks for having me on.



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