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21. Entrepreneurship + Mental Health: Optimizing For the Life You Want

21. Entrepreneurship + Mental Health: Optimizing For the Life You Want

Warning: We’re getting a little deep on today’s episode. I’m speaking with Josh Boone, agency owner for DTC eCommerce brands and we’re discussing what it means to optimize for the life you want and creating a business that actually fulfills you. Hear Josh’s story from running himself ragged with his first business venture to how he supports founders today to create businesses they love to run instead of businesses that run them. And listen through for the untapped marketing platform where you'll find your target customer all in one place!

We totally connected over our mutual disdain for the way most consultants operate, and how we do things differently when working with clients. His consultancy delivers an innovative and holistic marketing strategy that simultaneously strengthens in-house marketing teams from the inside and fortifies more consistent revenue streams. 

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Why is optimizing for the life you want so important to you? 

It's important for two reasons. Firstly, it's something that I've lived through and something that I struggled with quite a lot. Honestly, I still do to some degree because that’s the life of an entrepreneur — always trying to find the balance. 

Secondly, after working with hundreds of different businesses over the years in different types of industries, I kept seeing recurring structural and cultural issues within organizations. Coming to these teams as an outsider, people would be a little skeptical. Unfortunately, I was one of the only people they felt like they could actually open up to. 

It’s heartbreaking how much people struggle and how often people stay at a company because they believe in the mission or the goal. That includes people in the customer service team to the development team to copywriters all the way up to the founders themselves. Sometimes founders might get 5 or 6 years into a business and it's like the business is running them rather than them running the business. It doesn't have to be this way.

How did you get started?

I stumbled into all this marketing stuff. I have always been creative and originally, I wanted to be a filmmaker.

At the age of 13 or so I got into web design and building websites. I started with my dad’s small tree business. We were based in Dayton, Ohio so not a lot of small businesses had websites at all so it was really easy to show up. But I wanted to know what was bringing people to the website so I started researching SEO and keywords. So I went from that to building my own websites to starting an agency by the time I was 22/23. 

I was working a hundred plus hour weeks — I lived, breathed and died for the business. Don’t get me wrong, I had a blast doing it but it really started taking a toll on me. I never really asked myself what am I optimizing for, it was just grow, grow, grow. I didn't have a purpose or a mission in life so the business became that until I eventually felt trapped. 

Imposter Syndrome snuck in and I started to have a bit of an identity crisis. Questions started to emerge like, who am I supposed to be as a leader? Who am I supposed to be as a business owner? Who am I supposed to be in general?

I started thinking existentially, what would I do if I only had a year left to live? The answer was not this. I wanted to travel and have my weird Anthony Bourdain type adventure so I got away to a small town on Lake Michigan and spent the day completely surrounded by the sound of waves and listening to podcasts and music. 

For the first time in years I felt like I could breath. I realised I was running my own business, so I could do whatever I wanted and I didn’t want to work 100+ hours anymore. 

Fast forward a year later, I had gotten rid of just about everything I owned, had sold my portion of the business, bought an RV and hit the road. Now every January I ask myself, was I happy with this last year? I want to make sure I don’t have any regrets. I want to make sure that I’m living in alignment with myself. 

What’s the difference between a consultant and an advisor? 

A consultant is someone who comes in and looks at your strategy whereas an advisor is more personally integrated. I didn't really expect to become almost like a business therapist. 

I didn't expect to become an advisor in that way but increasingly I saw the need for advising because these founders often felt so alone. They like to march to the beat of their own drum, but most people aren't wired that way. It becomes a personal conversation because they don't ask themselves why they’re doing these random acts of improvement. That ends up translating to the business and the mission, which eventually goes down to the team. You end up with all this fragmentation, which is when people start hating their lives and not wanting to work there anymore. It just goes downhill from there. 

What is the first step that you take with the companies your work with? 

Usually it starts with someone needing help with their SEO or marketing but it often turns into a conversation about why they have a business. 

I ask them what their goals are and we chat about strategy and getting everything into alignment through performance marketing, branding or positioning. But as you start having the conversation about what their brand truly is and what assumptions can be made about their brand and their customers, founders start thinking about those same things in their life and you can begin to ask them why they’re even doing what they’re doing. 

I can't tell you how many times a conversation about SEO and marketing has morphed into a conversation about why they do what they do. Then we start talking about why I left my business, and that’s when we hit the core of it all — more often than not they feel unfulfilled. 

As startup founders, they have this imposter syndrome which makes them feel like they can’t open up and be vulnerable and it causes a lot of repression. That's one of the reasons why I'm so vulnerable when having these conversations is because I want to try and help change that and make it so we can all be more honest with ourselves.

How do you approach the holistic marketing concept with them?

The original goal was to create a more holistic structure for these businesses where teams can work collaboratively and just have a better life. But it became really apparent that the founders really lacked guidance themselves. As I talk to them about strategy they would say that they want to hit a specific KPI so I ask them why? They say they’re thinking about the next round in the next six months so it would be good to have these various metrics. 

So I ask them why do you want to raise another round? Sometimes they have a very good reason for it like they want to upgrade their facilities but other times they say they want to scale faster. When I ask them why they want to scale faster, that's when they start opening up about what is really important to them. 

We can talk about all the strategies and the tactics but if it's not ultimately creating the business that you want or that you envisioned, then it's not the right thing for your business. 

We see people from the outside and we think wow, they have it all. They must be so fucking happy but a lot of the time, they’re fucking miserable. They have to run away from their business — just like I did when I ended up traveling for a year in an RV.

Using Reddit to show up authentically on Social Media

One way that you can actually show up in an actionable and really sincere way is Reddit. Most people don't understand Reddit and they kind of tried to avoid it because they just see the pitchforks come out and I just see brands getting eviscerated on there, justifiably so. You can't go on there and just try and selflessly promote yourself or your business, because they will tear you apart.

But, if you're authentic, they will love you. So many celebrities and brands have gone on there that nobody really gave a shit about. But through authentically answering questions and being present, people start to turn around and say I love you. They start championing businesses and people and from there you start seeing way more articles and way more stories about them. 

You have to really show up authentically and be part of the conversation on Reddit and it’s what you should be doing in your marketing anyway. 

Instead of looking at business as a vehicle to get you to some destination, how can you make the business what you really enjoy doing? 

Find your sense of purpose. If you just keep going and going, reaching for those dopamine highs and ignoring everything else, you’re going to hit that point where you’ve done everything and you’ve been everywhere. You have achieved everything you want to achieve and there's nothing left — and that is scary. 

The first step is acknowledging there is a way out. You have to go through that hero's journey, you have to go through the darkness. If you wait and you hold off until it's unavoidable, you're not going to be prepared to handle it. 

Veterans and ex-cops feel this a lot. They’re constantly chasing the next thing that when they don't have that, all of a sudden they don't know what to do. Physiologically, you get so used to the rush and the high then you just cannot calm down. 

This is the exact thing that a lot of entrepreneurs deal with because they're just constantly hustling and grinding, searching for the next thing that when they actually reach the point where they’re no longer hustling, they don’t know what to do next. 

You feel like you're going crazy because your brain is optimized to run on all cylinders. If you have nothing to focus on, you begin to focus internally and it’s too much. I think that's what makes the suicide rates among vets and entrepreneurs so high.

So I would say you need to prioritize this internal work now. Don't wait until you retire or you exit — start now. I hate saying like unprecedented times but let's just be real, these are crazy fucking times people, so it's really important that we are taking care of ourselves. 

It doesn't matter how successful your business is or how much revenue you do, if you build a business that you don't love, or that doesn't support the life you want for yourself, you're still not going to be happy. It's not going to fill that void for you and you're not going to feel successful. 

What’s a tactic or strategy that you tried that didn't work? 

There's not really a specific tactic that comes to mind immediately. The thing that comes to mind immediately actually is more like the overarching kind of viewpoint. 

I’ve worked with companies that scaled really, really fast. They went from having a handful of employees to 100 employees really quickly, so a lot of what I did was come into a business and ask how can we reverse engineer this? How do we turn the freight train around? How do we get this optimized? How do we make sure they're going in the right direction? How do we get all these teams working collaboratively?

Starting backwards to help all these businesses course correct. One of my biggest failures overall was the first brand I worked with. We tried to do too much too soon and we overextended ourselves. We knew what the end goal was so we started trying to do everything at once — PR, social media and all this other stuff. It was crazy and they just didn't have the team or the resources to really execute all that at once. 

I also wasn’t as stern with the founder as I probably should have been. I gave my two cents but they started going in certain directions against what I had suggested. 

I wasn't thinking in terms of an advisor, I was thinking about it like a consultant. I thought my job was just to sit there and tell them what I think and they could either take that advice and run with it or they could choose to go in a different direction. 

What I didn't realize back then, particularly with younger founders, a lot of what I should’ve been helping them with was mentoring and steering them in the right direction.

Ultimately, it’s their decision. I can't run their business for them, nor did I want to, but I think I should have been a lot more adamant about steering them away from a couple things. 

Your competitor has blind spots, but so do you

In terms of strategy, I would make sure you’re aware of your blind spots and opportunities. You have strategic blind spots internally that you need to deal with and your competitor has that as well, which are your opportunities. 

The thing to keep in mind is that your blind spots internally are also the opportunities for your competitors. If you don't get that stuff dialed in, they're going to take advantage of that one way or another. 

You really want to try and get your existing channels optimized but the problem is people try to do too much. They just try to tack on more and more things and they don't get their stuff optimized so they get spread too thin. They start doing random acts of improvement and their team is running around like chickens with their heads cut off. 

Focus on a handful of channels — get those really loud and go really deep. This is an art form in a way. You want to get everything optimized, you want to get it dialed in, and then you want to start diversifying. You have to have to have a balance of yin and yang. I think COVID has been unveiling the inefficiencies that were already there and speeding them up. 

For example, say you relied entirely on paid social media for your growth and that has taken a hit recently. Your competitor also relied on paid social, however, they diversified and they're on Reddit, they have their email marketing setup and dialed in and they also have a great search and content strategy. They have diversity so when their paid social took a hit, guess what? It didn’t matter to your competitor because they had a variety different channels optimized. 

Do you think that there's like an optimal amount of time to focus on one channel before moving to the next? 

Do one thing really, really good instead of a bunch of things half ass because it's going to be so much more powerful. But you can't do one thing forever. It's entirely dependent on what you are optimizing for. Think about that in terms of what success looks like? What does success look like two or three years from now? 

Strategically, the biggest thing is dialling in on what you are actually optimizing for and then setting some very specific metrics, like quantities or KPIs. 

Then the other side of it is more of the philosophical — what are you actually trying to accomplish? That’s the yin and yang, the high and the low, the macro in the micro. 

You need to set that balance for every channel. For example, if you wanted to be on Reddit, how would you communicate with that audience in an authentic way? A lot of times founders have an overwhelmingly good amount of resources for positioning, but they are shit at being able to get it down into actual words. 

Your goal is to develop a real relationship with people on Reddit and start pulling it together and building some brand recognition, what's a KPI for that? Do you want to create your own subreddit and start like getting people in there? After you’ve dialled in on that, then you move onto SEO and content strategy. 

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Hey, I'm Jessica

I support scrappy female entrepreneurs with actionable steps & strategies to grow and scale the traffic, sales & profit in their eCommerce businesses. 

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