TMBA558: Are You Running the Wrong Kind of Business?

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In past episodes, we’ve talked about “Founder Fit”, or the idea that you should be running the type of business that is best suited to your own personality and lifestyle.

But what happens if you’re not doing that?

It turns out that having a bad fit between you and what you’re building can potentially lead to a whole lot of pain.

Jesse Hanley is all too familiar with this experience.

Jesse is the founder of an agency called TalentTree, and he recently made the decision to shift the focus of his agency to a productized service model in order to fund the development and growth of his new software company Bento.

Jesse joins us this week to share the emotional toll he experienced running that agency, why he decided to make drastic changes to his business to improve his quality of life, and how he has been able to find a large portion of his clientele on a rather unexpected platform.

See the full transcript below


Listen to this week’s show and learn:

  • How Jesse got his first break managing eCommerce for a supplement store. (3:02)
  • Why the story that we tell ourselves is so important. (11:40)
  • The turning point where Jesse knew that something needed to change. (15:45)
  • What led to the creation of Bento. (28:37)
  • How a small Twitter following has led to seven figures of revenue in Jesse’s business. (33:30)


Mentioned in the episode:

Before the Exit – Our New Book
TMBA Masterminds
Partner With Us
The Dynamite Circle
Dynamite Jobs
Dynamite Deals
Tropical MBA on YouTube
Jesse Hanley
The 4-Hour Workweek by Tim Ferriss
Happy by Derren Brown
Tommy Joiner

Enjoyed this podcast? Check out these:

TMBA503: What’s Your ‘Founder Fit’?
TMBA531: A Lot Can Change In a Year
TMBA557: Ascending the Staircase


This week’s sponsor:

Today’s podcast is sponsored by Smash Digital.

Smash Digital is a growth agency filled to the brim with unicorn images and SEO memes.

A team of SEOs who actually know how to use SEO instead of just selling SEO to people who don’t know SEO.

An agency with so much link juice, you’ll need a mop and a bucket to clean it all up.

A group with actual skin in the game, ranking their own portfolio of profitable businesses, and offering the exact same services to clients.

If you want to have Smash Digital in your back pocket, check them out over at and a big thanks to Smash Digital for sponsoring the show.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian






Full Transcript

TMBA Ident

Dan: Hello from Colorado. Welcome back to the TMBA pod. Wherever you are in the world today, I hope we can bring you a little bit of positivity and inspiration on today’s ep. I know I had a wonderful time producing this episode.

Today we’re going to talk about the stress, the struggle, and then the potential satisfaction of finding a business that is a good fit for you. I’m going to talk about this concept of founder fit. I’m not talking just about your bank balance, which of course is important, but also as a person, because if you don’t find this fit between you and what you’re building, it can potentially lead to a whole lot of pain.

Jesse: I was in my little white Airbnb and I was crying. It was just like too much. A good analogy was – I was standing there, it was almost like everyone that I was in contact with had cables attached to me. So all my clients, my team, contractors and you got these like hundreds of cords, all plugged into you.”

Dan: You know that feeling? Who of us canot relate to an incredible amount of stress brought on by our business. Today’s guest is here to talk about that and more. His name is Jessie Hanley, someone our team has been working with recently. And after a few years of travelling the world, Jesse is currently based in Japan.

He’s the founder of BentoNow, a software company that does email marketing and live chat, and also the content agency called Talent Tree. So we’re going to get into lots more details about those businesses as this story unfolds. I gotta say in person and on Twitter, and in the DC Jesse is very approachable and generous. And I think it shines through in this interview.

Just some of the few things will cover Jesse’s path to becoming a software developer without traditional training, his use of Twitter to find an extraordinary number of customers, and why it’s important to find and follow your unique narrative, rather than the one that’s been advanced by those around you.

So let’s get to it. Jesse’s story starts in Sydney, it’s around 2010. He’s 18 and has skipped going to college to focus on bodybuilding and becoming a personal trainer. And what better place to advance all that and taking them by taking a job in a supplement store.

TMBA Ident

Dan: So you’re working in the supplement store, you’re pumping iron.

Jesse: Fat burners, testosterone boosters, protein powder, all that stuff. Yeah.

Dan: You get bored. So you build them an Ecommerce store, what happens next?

Jesse: It starts making money. And the boss comes to me and he goes, I want you to come down to Canberra. Let’s put someone else in the store and come down the Canberra and build this, like supplement empire with me. And the guy had a lot of confidence. He came from like x bank in a pretty jacked guy as well. So a little bit intimidating.

I basically packed up all my stuff in Sydney and went down to Canberra to move in with like another bodybuilder. And it was just like a hilarious journey, like three to four years. During the time, it’s like a quick recap. We basically grew the e commerce store to one of the top ecommerce stores in Oz for supplements. And you know, we’re buying backlinks and doing all this type of shady stuff, but it was early days, so you’d like you could do it and pull it off. I’ve been listening to the ‘Four Hour Workweek’, and had heard about ‘Get Friday’ on that. And so we like we hired them to basically do all of our content strategy.

Dan: And ‘Get Friday’ was like a virtual assistant service. Is that right?

Jesse: Totally, and what’s kind of interesting about this business was um, we had the supplement stores but also we created a distribution company. So in Australia, basically all the supplements we imported ordered from the US. And we were buying from distributors.

But we’re like, why don’t we just make our own distributor. And so we did. But no one knew that they were related because we sold to all of our competitors as well. So we kind of had the secret distribution companies that existed to sell it to ourselves to get cheaper margins on goods, but also sell to our competitors to make money off them. It was this very complex setup. They started doing extremely well, and I was involved in all the upside so basically worked with the boss over time on a lot of the operations and the systems.

So a lot of the marketing chops that I had was actually him just giving me too much freedom at the time. Just basically being like, ‘Just do whatever you want just make more money’. As long as he saw that it was in the grain. He was super stoked. And then when it was in the red, he’s like, ‘Fix it’. So yeah, it was very much like a cowboy time.

Dan: How many stores did you guys have?

Jesse: Maybe like 12,13, 14, 15 spread throughout Australia. So all up the East Coast and some down south. We used a software called NetSuite, which is like an enterprise management platform for the distribution companies. So I like set that up way too fast. It was supposed to be like a six month integration like we did in a month. And the integration partner was like, because my boss was like, so ‘How fast can get this done?’ And I was like ‘Six months, and he’s like, ‘Do it in a month’. Try. And I remember calling a lady called Joyce at NetSuite. And she’s like, ‘Please don’t go live. It’s not ready’. And I was like, ‘But we have to’.

But yeah, a really bizarre time and with that business, so again, to recap, we had the supplement stores, the ecommerce store, and then we had the distribution companies but then we also bought the master franchise rights to Gold’s Gym and then started opening up gyms. And that was a big one because the master franchise rights to Golds was very expensive.

And then over the course of a few years, open some gyms, open some retail stores. But then stuff started to get a little bit tricky with the Aussie dollar tanking, so like a lot of our margins were importing goods. And so as the Aussie dollar started to tank so did on margins. And I started, because I think I had visibility on a lot of the financials, I started to see that and, again, I was listening to your podcast, I was listening to the ‘Four Hour Workweek’, I started to convince myself I needed to just get abroad.

And I convinced a remote working arrangement with him at the gym. So I remember walking up to him during a set and being like, ‘Hey man, I want to I want to go travel’ and he just looks at me and he’s like, ‘Why, what are you gonna do because like you run, you know, you run the whole ecommerce Ops, you run the back end a lot of the systems that we’ve built for the distribution companies’, and I was like, ‘I can do them online’. Yeah, kudos to him. He was just like, ‘Okay’, and then just kept training.

Dan: So you’re on a wild ride. And you’re like ‘Let’s just make it even crazier’. I’m gonna interrupt this guy’s chest flies and I’m gonna say I want to get on an aeroplane? So where did you go?

Jesse: I went to Thailand. I went straight to Bangkok. Maybe your podcast and maybe some other ones and the ‘Four hour workweek’, I think just kind of it places that seed. I think it takes a few years for that seed to grow. But it was almost inevitable that I think I would have ended up there given the media that I consumed at the time.

Dan: Does Thailand deliver on the unspoken promise? In the blogosphere

Jesse: I think so. I think Bangkok did for me. I love Bangkok I, I find it’s an adventurous city to be in, it has a lot of energy. But a couple of friends like I’ve mentioned a lot of cities whisper certain things to you. And Bangkok wishes very loudly to me, there’s a lot of chaos. And if you have that energy and you can match it, it’s good.

But I think every time that I’ve been in Bangkok and I’ve been running my business, often I’ve been overwhelmed with my business and being in a city that’s overwhelming hasn’t been good for me. Whereas in cities like Chiang Mai let’s say in Thailand that has delivered, it’s a calmer city. I can kind of control the noise around me. And it whispers ‘It’s okay. Everything’s under control, like just focus on your stuff’. And so in terms of Thailand cities for me Chiang Mai delivers.

Dan: So let’s then, if we can, fast forward to what was the breaking point with this company where you decided to become an entrepreneur.

Jesse: I was forced to, so I was in France, having a coffee in the morning and I had just a great weekend, and opened my laptop. And one of my colleagues is like ‘the businesses bust’. And so I’m like looking at this email and I’m like, ‘Ah, bugger’. And I was kind of forced to do it, because I was like, like, I’m playing this game, right? Like, I’m travelling and I think for the first it was about six months, I was on the road, and had been through the US, had been throughout Europe, and I was kind of in that Europe, three months bit.

Dan: Now what year is this?

Jesse: This is a 2015.

Dan: And, it sounds pretty fun.

Jesse: It was a really fun start of the year. At the time, like I was still working full time, but again, because I was kind of seeing the tea leaves, so to say, I started kind of preparing. So I was making a lot of friendships out of a lot of communities that I was hanging out in.

I spent a lot of time in like SEO communities. And I found a partner at the time for a, like a small agency that we kind of created out of thin air and had like one and a half, maybe two clients, along with my full time job. And so when the email came through, it wasn’t like, like Doomsday. It was just like, ‘Oh, I’ve just gone down from like, my salary was, I think, between seven to nine thousand Australian a month down to like two or one grand. And so I think at that time, I was like, ‘Okay, cool. I need to take this seriously and I have to make this work’.

Dan: I feel like I want to zoom back just really quick. I hate to interrupt the story. But you know, I’m noticing reading through your story that you were able to connect with the people at the top of these organisations, even when you rocked in with no experience. It doesn’t feel like that’s possible for a lot of people. So why was it possible for you?

Jesse: I think my first job, like reflecting on that, my boss at the time, gave me a lot of permission to just go for things and get in rooms with people that were bigger than me and it was really uncomfortable, like being 18,19, being in a room of guys that are like 30 to 40 and I’m like pitching them deals or I’m negotiating something or, you know … again at like 18, 19 being on a call with like a large agency, like all that stuff’s really intimidating and I think it was because I do feel like I never had much to lose a lot of the time.

Dan: Here’s what I was thinking right before you said that. I was thinking. ‘I wonder if it has to do with the fact that he has less ego. I wonder if it has to do with the fact that he’s object oriented or mission oriented. I wonder if it’s because Jesse’s a good soldier in that sense’. In other words, like the journey was of primary interest to you not necessarily what your benefit was going to be from it in the short term.

Jesse: I think what’s been really important for me is like the story that I tell myself. And I haven’t really been able to articulate that kind of saying of the story that I told myself, since a couple of years back when I read a book called ‘Happy’ by Darren Brown. It was it was a really good book, but one of the things that he mentions is like, ‘Yeah, the story that you tell yourself is like one of the most important things’.

Dan: Is Darren Brown The Illusionist guy?

Jesse: Yeah. And he kind of wrote a book kind of on stoicism. But the general theme of the book is the story that you tell yourself is the most important thing. And, and evaluating the story that you do keep telling yourself is generally a good reflection of how you feel. And for me, l think when I was young, the story that I told myself was like, you know, ‘I love business, I’m in business. You know, one day I’m gonna have a business of my own and like, I need these skill sets’. And so whenever anything was too nerve racking, I would just be like, Alright, but like, this is where I want to go and like, this is how I see myself like, let’s just keep at it and give it a shot. I don’t really have much to lose.

But I do want to put emphasis on one of the reasons I feel like I don’t have much to lose is I’ve a really good family support network. And so for me, knowing that I have a mom and a dad I can call up and get help with in terms of not financial, they’ve never given me a single dollar, but in terms of love and support, that gives you so much confidence just to go after stuff. And my dad’s always told me that he’s like, ‘You’ll always be fine’. He’s like, ‘So just go for it. Like, you’re gonna be okay’. And so having that support. I think here’s why I’m comfortable taking a lot of risks.

Dan: I’m curious about that process of like, workshopping your story. What does it even look like? Like, what’s an example of a story you could tell yourself and how might you adapt that story?

Jesse: The story that I’m telling myself now is like, ‘I’m a good boyfriend. I live in Japan. I’m learning Japanese poorly. And, I’m working on a software company each day. And I’m a good leader to my team’.

And I’m trying to simplify it now to reduce a lot of the anxiety. I’m trying to keep the story that I tell myself very short, in time lines. So it’s mainly, ‘What I’m doing today, like who I am today, and the type of man that I am today’, versus like who I want to be in the future. And I found that to be tremendously helpful. Both in terms of reducing anxiety and in terms of my own direction. For me, if I wake up every day, I write great code, and I work on stuff that I’m passionate about and I’m like a good leader to my team, I’ve had a good day. And I’m kind of proud of that. I’m almost sure that if I just keep repeating that the momentum is gonna get me to, you know, an aspiration or a goal down the line, but mostly focused on just keeping stuff to today. Does that make sense?

Dan: What do you mean by anxiety? Yeah, it does make sense.

Jesse: I just feel like when you do think,so far forward, especially in the early days, you know, the first thousand days when you’re like, how am I going to get to my previous salary? There’s just so much anxiety not knowing how the hell you’re gonna get there, right like my path to getting where I am now, where I was able to take like, a long weekend off in Yakushima with my girlfriend and not touch my computer, that’s been like five years in the process.

And there’s a lot of anxiety just trying to … almost like your eyes are shut and you’re just feeling around the room trying to find the door. And the first thousand days does feel like that. And that anxiety is good, because it keeps you alert, keeps you open opportunities. But for me, personally, it built up to a pretty scary point a couple of times. And so for me, it’s nice to have less of that, I think.

Dan: I really relate to your idea of anxiety being like a spice on the entrepreneurial soup, the way you put it maybe it hasn’t quite been on the show before. Where does it get too scary? How do you ‘check yourself before you wreck yourself’ kind of thing?

Jesse: So in 2018, at the time at an agency and that agency was

Dan: The agency that you started developing after your business imploded underneath your keyboard?

Jesse: Exactly. So basically like to do a quick recap. I started consulting immediately after I lost my job. Picked up clients. I hired my first two team members, and then built up kind of a full service agency, I had an ops person, I had like a head of SEO like that kind of typical thing. All I was doing was basically closing deals, working out how to do that work, and then hiring people to make that happen. I was involved in everything. And we got to the point where I think we were doing, like, I don’t know, 35 to 40,000 a month, and I was completely wrecked.

I was in Slovenia and I was so overwhelmed and frankly like I was depressed and completely wrecked. And I was in my like little white Airbnb. I was emotional, I was crying. It was just like too much. It was kind of – a good analogy as I was standing there, it was almost like everyone that I was in contact with had cables attached to me. So all my clients, my team, everything, contractors and you got these like hundreds of cords, right? That’s all plugged into you. And it makes you so claustrophobic and I yeah, I gotta try not to get like a bit teary”. Sorry.

Dan: Dude, a lot of us relate to this shit. We’re doing hard stuff.

Jesse: It was a pretty scary point. And it was really overwhelming. So I called my dad and I flew back to Sydney, and basically sat down with him and reevaluated to the business. And for me, that actually looked like completely shafting in the whole company. And starting again.

Dan: It sounds like a situation that a lot of service business entrepreneurs can find themselves in, where you ultimately build up the skill set that was super valuable at an e commerce company that you did everything for them. So now every client comes along and you can say like, ‘Dude, I can take care of your business. I can do SEO, we can do some dev stuff over here. We can run your PPC campaigns over here. Exactly. You signed the $5,000 contract, you’re meeting your revenue goals, like you dumped the work with your contractors, they’re confused about it a little bit’.

And so now all of a sudden, you got to a world of mess. I’m actually curious, like, not to dig back into it too deeply.

Jesse: I’m good now.

Dan: But specifically like, what were the sort of like, behaviours that led to the anxiety? So was it like, was it clients being angry? Was it stuff not getting done or paid on time? Like what were the things that started to break in the business that made you consider getting rid of the whole thing altogether?

Jesse: It compounds over time, and you don’t really realise that you’re getting into this kind of crux point. So, for me ,the time when I was in Slovenia, upset, depressed, sad, that was basically a compound of invoices not being paid. And I was generally really good at this, after running like the distribution company. I was like, ‘I’m never going on terms’ and so everyone at the agency, doesn’t matter what they were on. I made everyone pay up front, but it’s when like, three or four of those go 14 days overdue, 30 days overdue.

It’s not that bad. But it adds the anxiety like – what happens if they what happens if they churn? Do I have enough cash balance to pay my team? And so even if I thought I was doing best practice around billing, around invoicing, I was always anxious that something would go wrong.

I think also, in the SEO side, when you are doing SEO, and you’re doing like link building and you’re doing content, there’s a lot of anxiety around that. What happens if I build a bad link? What happens if the link building doesn’t work? I really cared about the work that I did. And this is going to be a weird comment. But I think that is not advantageous for a successful agency, especially an SEO agency. The most successful SEO agencies that I’ve seen, from a business perspective, not in terms of the work that they do. They generally are very good at sales and marketing, and not very good at deliverables. The agencies are really good at deliverables, sometimes they are better off working for themselves on their own projects. It’s a lot less stressful. Does that kind of make sense?

Dan: Well, it sounds like you had a hard time drawing the line because it’s like, ‘Hey, I delivered all these links and content to you. But we, as a company, as an agency still feel like that’s our product’. And like a good agency sees it go out the back of the truck and delivers to the customers, like, ‘You guys deal with it’. You know? It reminds me of talking with Tommy Joiner on the show. And what I thought was so interesting about his business was that they specifically would not sell results. It’s like, you are literally buying like this, concrete info piece of value from us and like that’s it.

I mean, I used to work for clients and I was anxious all the time. Because there was literally 1000 things that could go wrong. And any one of them would trigger a phone call to me. And 99% of them were out of my control. That’s the other thing that that can be difficult.

Jesse: I think the other thing as well as like a lot of client agency success is actually I feel mostly dependent on the brands themselves. And this is me kind of like pulling back a bit, but like good successful brands paired with like a good agency kind of like take off. So you know, brands that are naturally acquiring links, brands that just have great processes and systems they do well.

It’s when you take a few of those clients that they don’t actually have like real companies or products yet, but they have like some cash and like you as an agency owner, you’re like, ‘I need cash’. And so leads come to me, I’m going to close them and start working for them. It’s not actually like a positive engagement.

And if you have a few of those, combined with everything else that’s going on, it gets too overwhelming. And again, I didn’t have a clear offering. I was a full service agency. We were running ads, running Facebook ads, running Google ads, doing SEO, doing content, technical SEO. I was doing enterprise SEO as well as consulting for large corps. I don’t know how I got into those rooms, but I managed to do it.

It was just very full on. And when all this stuff kind of compounds, my own expectations of myself, my team’s expectations, people asking for pay rises, people are asking for new responsibilities. And you know, they’ve got their own aspirations. It was just very tricky, and I don’t think I was actually capable of managing employees that well at the time just because I didn’t know how to .. I didn’t have any like an agency mentor. So I was just doing all from first principles as well and and I don’t think I did it well, if I’m gonna reflect on that a bit

Dan: So then, if you could zoom back then, and be the business coach for ‘the Jesse who wants to persevere’ in that situation, what’s a good positive business move they can make in that situation? And then what ultimately did you decide to do?

Jesse: Sure. I mean, looking back, I don’t think I would have changed a thing in that agency. I made so many great relationships. So many great friendships, people that pay me for Bento today, were clients four years ago. And in a way, like, as I was reflecting on, you know, my first job where I basically I got so much permission to try different things. The agency also gave me permission to try things. It taught me how to learn Facebook ads at scale, they taught me how to learn Google Ads at scale. It taught me how to run a content team at scale. The agency taught me loads, it just got to a critical point where it became too overwhelming for my personality type.

So when I flew back to Oz and sat with my old man to be mentored, we basically realised that there was one critical offering that I did offer in the agency, which was we basically hired full time writers for people, you know, e commerce firms and affiliates, and I loved that business.

And the team of that business, but what it would have required was me essentially laying everyone off but the writers and then building that again, and that emotionally was really hard because I’d never laid anyone off before. And so that journey of laying people off – I essentially found everyone new jobs. And it took me about a month but I found everyone new jobs, either at clients or friends of friends companies, and then started again with Anna and Anastasia.

Dan: So just zooming in to give a little bit of context, so Anna and Anastasia now lead a team of 20 to 30 at Jesse’s company called Talent Tree, which has a productize service offers access to full time high quality writers based in Eastern Europe now as a productized service. There’s both upsides and downsides of those business models, as regular listeners will know, something we’ve been talking quite a bit about on this show. So I’ll get Jesse’s perspective on that. Now to Jesse

Jesse: The company is now larger than it was. And we only offer that service. I just do sales for that business and even lightly so now and it runs really smoothly. Clients are really stoked. The business whispers such different things to me than the previous one. But same revenue, higher margin. Again, I don’t think I would have got here without going through all that kind of shenanigans before. It’s just really hard at the time I think, you know, I got emotional before it’s, it’s hard.

Dan: And it’s even harder to say no to revenue.

Jesse: Yeah, a nice paycheck that you’re just cutting yourself. And at the time, just to give some more context, I basically was grabbing money from the agency and deploying it into other assets. So I had bought affiliate sites, which was interesting because it kind of hedged things a little bit. That was a nice decision. I bought an affiliate site that was paying enough to cover rent and food for me. And by the agency buying that affiliate site, I was like, ‘Even if everything goes to zero,I can just hang in Chiang Mai and hang with Dan’.

Dan: That is such a millennial rich, ‘Rich dad, Poor dad’ move. I love it. It’s like a new class of assets. Other words, you’re going out and you’re making sure that your passive monthly income is greater than your expenses essentially.

Dan: So we’re just taking a short little detour here with your productized service and I want you to comment on whether or not you think prototype services are overrated, which is a topic we’ve been discussing a little bit on the show here in the last few weeks.

Jesse: I wonder if it’s like ambition. For me, my ambition now for Talent Tree is essentially like, Talent Tree is my ‘in quotes’ VC fund for Bento. So when I need money, I just pull it from that business. And that’s how I actually see that vehicle. And it pays me a salary, so pays me a salary and I use it as kinda like VC capital when I need it. And that’s my only ambition for that company. It grows at the rate that it’s comfortable growing. So like we’ve got a lot of leads. And essentially, when we find a good writer, a new writer, we close a new lead and then add them to it. But often I’m asking Anastasia and I’m like, ‘Oh, how are you going with workload? Do you want to close another lead? Or do you just want to focus on existing clients?’ and when they’re like, ‘Oh, we want to focus on existing clients’, and we just don’t really do anything. It’s a very relaxing, calm business, which is what I always wanted. It’s just taken a while to get here.

So, for me, I don’t think they’re overrated because, that business being a productized I service. It helps me build strong relationships with my friends, because a lot of my friends also hire writers through us. I still get exposure to great companies. And again, it’s a good cash flow vehicle, we’ve got really good margins. So like we operate on, I don’t know, 50 to 70% margin, depending on the writer. So like, pretty healthy.

Dan: So you bought us to 2018? You basically became a personal recruiter for all of your ex employees and found them jobs, tell me about the move into Bento?

Jesse: Sure. So it’s been like a bit of a journey. But we’ve kind of come to, I think a nice point of product market fit this year. But Bento is essentially, real similar to brands like ConvertKit and MailChimp. We send email marketing messages, broadcast sequences, workflows.

But whilst building Bento, we’ve kind of gone through this journey. Bento has been a lot of different products, and in the last year has found itself. And because we kind of went this more complex path, we didn’t really start at the email marketing part, we actually started at analytics and personalization, we ended up building a lot of these kind of really great tooling around tracking and around web personalization.

And it has led to an email marketing product that, in my opinion, serves marketers better, the tracking is a lot better because again, we’re using web tracking you can tie things together. So you know, with your automation, you can send an email at the right time, but then also update the web copy on the website to match a certain email that they’re getting. You can hide elements on a website. It’s more like an email marketing product for professionals. And I ended up building it for myself and have, you know, sold it to others. And it now feels like a real company now, which it’s been a bit of a journey to get there.

Dan: Why don’t you just become an affiliate marketer or something? Why not just keep a healthy stable of sites that sell protein powders and stuff like that and ride off into the sunset.

Jesse: I feel like business selection is mostly tied to identity and personality. I like talking to people, I like hanging with people. I get a real big buzz of being involved with customers’ projects and stuff like that. So for me, especially with Bento now, like, I have customers in my Slack that I’m very intimately working with on like a daily basis, even if they’re paying $15 a month or 100 bucks a month or three and like, it may not financially make sense. But for me, it’s very fulfilling and rewarding, which is what I want my day to be like.

Because my productized service is spitting off enough cash flow to pay my salary. And because like, I don’t really need to worry too much financially at the moment touchwood, the things that matter to me most of these kind of more long term vision things. I guess like for me working on a software business over the long term, making it better, working with customers, that’s what I really enjoy.

Dan: You mentioned identity and personality multiple times in this conversation, Where’s all that coming from? Identity is not a word that people toss around very often.

Jesse Yeah, I just feel like a lot of the decisions that one makes, I feel in the early days, like it’s hard to know where you fit. But after a certain point, maybe after ‘the thousand days’, you have some success under your belt, you have some relationships, you’ve kind of created your own identity and you had whether or not you’ve realised that or not.

An example of this recently was, um, I got hit up by a competitor to invest in Bento, which was really exciting. But identity wise, I still want to, for some reason, I want to do this all myself. And I wanted to have full ownership and I want to invest in the product myself and invest in myself. And so I kind of pushed that deal aside and ended up kind of not pursuing it for .. I basically said, I wouldn’t pursue it for six months. I put off the decision for a little bit.

Dan: I love it. So investing in yourself is obviously an enormous theme of this show. So Jesse grew up seeing his father run a software company and knew that eventually, he wanted to do that too. And for this part of his journey with Bento, he’s chosen an interesting way to achieve that over the last three years by learning to code, something so many of us that are non technical, have considered seriously doing and he did that by deploying his favourite social media tool.

Jesse: The first developer that I brought on to the project, Andrew Culver, he was someone that I’d followed on Twitter for a really long time and someone that like I respected and I actually caught up with him in Tokyo, pitched me the idea and brought him on, he was the first contractor and kind of the deal was, I’d bring him on as a contractor. And he would help me build the tool.

And that was about a year of development. And in that there’s like mentorship, right? Like he’s committing code. I am looking at it, reading it, understanding what he’s doing, making small changes, but he’s kind of mainly focused on the more complex thing. And over time, he slowly phased out and then I slowly took more responsibility for the code. But whenever it’s been like a complex problem on the dev side, I brought in other people that are much smarter than me, got them to do it, looked at how they’ve done it, learnt, and then I can kind of take over that code base and improve myself.

Dan: You wrote. ‘Every week I set aside about eight hours to help other online business owners with their e-commerce and SEO strategies, at any stage, for free. It helps me sharpen my skills, and I’ve made some lifelong friends this way’. What’s that all about?

Jesse: So one of the smartest things that I did early on was I just put a, there’s an app called Calendly, which essentially allows anyone to book a time in your schedule. My Twitter bio, for the first three, four years was my Calendly link. And so people would come across me on Twitter, book a call with me. And then I would talk to them, and depending on the size that they were, so generally, like, I would mostly just help people out and then the call would end and it would be awkward, because they would expect me to pitch them something. Like, I basically helped them for like an hour and a half. And then I’d be like, ‘Cool, man, like, have a great day’.

Then they’d be like, ‘What?’ But those relationships down the line, you know, people would come back and either like they would hire us for Talent tree hire us for Bento, well, like they’re just be really good relationships and friendships or on the opportunity side.

Recently I got an offer to buy a site from a friend I chatted to maybe four years ago. So it has opened up a lot of relationships and friendships and opportunities, just by having that like one little optimization because I love Twitter. I like Tweeting. I don’t have a large following there but it has been the number one source of leads in business since the beginning. And as probably netted over seven figures in revenue just from tweeting with a small audience, which is cool, and again, that the process has essentially been someone accidentally sees a tweet of mine, one of their friends likes one of mine, so it appears on their feed. They check out my profile, they see that I do x and y, click on my link, talk to me about SEO because that was what my profile was kind of optimised about. And then I would just chat to them, help them out.

And then if I felt there was a sales opportunity that I would close, but if there wasn’t, then I would just help them out. And another benefit was, I’ve helped someone out. And then they’ve introduced me to people, at pretty decent sized companies who just happened to be friends. Almost all my enterprise SEO gigs, the ones that I’m really proud of. They happened that way.

Dan: So this is very curious to me because there’s not a lot of marketing writing about people using Twitter in this way that I’m aware of. And Twitter’s changed a lot in the last few years and I’m a little older. I didn’t realise how much money people were making from Twitter. And I’m wondering if you can help our audience to think about how they might make money from Twitter.

Jesse: Most people, when they’ve got downtime, will open Twitter and just kind of like scroll things that they’re interested in, right? And so on. Like for you, and for me, like it’s an escape whether, I don’t know who you follow, but let’s say you follow like cyclist accounts and some startup people and all that. Generally the people you’re following are like founders of a business or their people, you know, at the top of their game. But also there’s not that much noise on Twitter, like, unless you have a very substantial following.

So a head of marketing at let’s say, a large SaaS company or a large, like e commerce has a pretty large community now. People that are running, you know, very large e commerce businesses, they’re just talking the shit on Twitter. And like, if you reply to them, they are gonna see it, and they’re gonna engage and like, if they’ve enjoyed that interaction, they will follow you. And this is what I don’t think most people realise is like, often a lot of sales deals, like people have to be in the right headspace and the right time to actually like be closed. And so in like email marketing, let’s say, people aren’t going to switch from MailChimp, Clavijo, Drip just because I don’t like did a good pitch, right? Really like, they’ve gotta be frustrated with their existing solution and be actively looking.

So often, if you’ve interacted with someone, they’ll remember, and so that when they do move into the market later to buy a service or an offering, you’re now an option in the selection.

And so for me, it’s like, alright, well, my job is to nurture good relationships, talk to people that are smarter than me and just kind of like, be a good netizen and just try and help people. And when it comes time that someone has a problem that I can uniquely solve, whether it’s hiring a writer in Eastern Europe to scale out their content, or whether it’s offering some pretty interesting email marketing stuff, then, yeah, then they’ll come and they’ll reach out and that is what has been happening basically since I started.

A lead that I’m closing for talent tree today, he’s been following me since 2015. Maybe the start, maybe the start. And it’s only now that he has a successful financial affiliate site and has enough revenue that he can afford to hire a full time writer.

If you like you go on that platform and you try and like hack it and like you don’t kind of treat it like a dinner table conversation then it won’t go well for you. People see through that. Even trying to be like mined for a relationship, that’s bad like when I go on Twitter, I just have fun.

Dan: Yeah, it reminds me something I thought about earlier while you were giving an answer, which is like, just provide a great deal more value than you saw, or than you capture. It’s not that hard to do, actually. And in fact, I thought about it earlier, when you were talking about how you made customizations and without the money in mind, and I thought to myself, ‘Well, yeah, as entrepreneurs, we don’t actually work for money’. You know, I haven’t worked for money for 15 years. Like I don’t do anything that people pay me to do.

Jesse: Totally. There’s also that kind of, like, maybe deeply ingrained thing, let’s say, I help you know you guys on your project, there may be a conversation or a dinner that you’re at much further down the line three, four, however many years down the line, and someone’s like ‘I hate, you know, my existing email marketing platform’ and you’ve had that, you know, good experience integrating with me. And you’ll be like, ‘Oh, you should talk to Jesse’. And that could be a huge life changing deal for me.

But that’s not really tangible. And it’s really hard in the early days to like, understand what that advice means. But I think after ‘The Thousand Days’, that’s something you kind of like, inherently realise is like, when you put a lot of good energy out there, it comes back. But you can’t really have any expectations for actually coming back. So you just gotta do the best that you can do.

Dan: There’s something short sighted often about just focusing on data and transactions, because those things are not efficient at actually capturing how our organisations pan out all the time.

Jesse: I agree. And then on the metric side as well, and this has been interesting like with Bento, we’ve got a large analytics portion of the product. Even trusting a lot of the metrics, like when you build open and click tracking for email, you then start not believing any of it because you actually realise how the cookie has been made. This is a hard point. I haven’t really been able to articulate this properly. But for me, a lot of them the metric driven decisions and metric focus stuff often misses the larger point.

Same with websites and stuff just because you have a lot of traffic and a small portions opting in doesn’t mean that a large portion doesn’t hate you for all the pop ups that you’re doing and stuff, right?

Dan: Correct.

Jesse: And that’s one example, on the email marketing side, people look at opens and clicks. On the open rate issue, like Gmail would just randomly open your tracking pixel, like 100 times, and it won’t be the user. And so like, do you trust that metric? In my opinion, like no, but the email tools aren’t really incentivized to like tell you that. Just like look at the opens you’ve got some tools that will trigger an open based on a whole bunch of like sometimes even statistically like there’ll be like we think it could have opened and then they’ll trigger and open that way. Yeah, I don’t know

Dan: We kind of get to this point in the conversation where I have a few wrap up questions. And it feels like, you know, part one a little bit. I’m working on software right now. So I feel like I should be asking you more smart questions about building software, but I just asked you about your mindset the whole time, like an idiot. Are there things I should have asked you about getting started in terms of product market fit, pricing, getting your first customers involved, and then finding a way to build a real business out of selling software to people?

Jesse: So a couple of points. I think software takes a really long time. And you need to make sure that you’re not just going into software because it’s like the fancy thing to do. It’s because you kind of deeply resonate with being like a software founder. I believe that that part’s true. And so for me, ever since I was young, I always wanted a software business. I couldn’t do that in my early years. I can do that now. But it’s taken my early years to build up the cash flow, the reserves, the relationships, the sales, like the ability to sell to be able to run the software company now. So that’s one point, I think.

Dan: So you ‘stair stepped’ your way like Rob Walling style, up to the ability,

Jesse: Yes, consulting, consulting agency, productized service SaaS. And my long term vision is actually SaaS to physical location space. I’d like to have an office that I can rent out to other people plus my team.

I miss being around people and I think having a business where I can put my own team in there ,they can come in, and come out, plus other people could be a nice way that I can get that and not feel obliged to check in every day and still travel and do all that.

But that’s kind of how I’m stair stepping. The other thing as well as I think, if you are a non technical founder, potentially learning how to code can be very advantageous. So for me when stuff is going wrong, fixing it immediately, and telling the customer ‘Hey, it’s being deployed right now, refresh your screen’. That is like the biggest competitive advantage I think I’ve ever had, especially when I’m coming into like the email marketing industry. Like I’m up against Drip I’m up against MailChimp, I’m up against ConvertKit and there’ll be like, ‘ConvertKit does this’, and then I’ll ignore them on Skype. And then I’ll be like, refresh we do it too like, be like, Oh, cool. Alright, so said that. That has been a competitive sales advantage.

And only now am I trying to like extract myself out more. And that’s bringing on one of the developers coloured to work on the product significantly more and then another agency in Ukraine called Coda Labs, also now working on it a lot more. And I’m trying to extract myself out because I’ve actually left marketing and positioning stuff to the wayside just to focus on product for the last while, but I think that’s been necessary. It takes a really long time to build a product that resonates with a market. And again, when you’re up against like, Clavia, hundreds of engineers, it’s just me. So like, trying to build a feature set that I can pull customers away from them is tricky, but very fulfilling when I actually do close those deals.

Dan: How it possible?

Jesse: Honestly, because a lot of people don’t use a lot of the features in these toolings so people will sign up to clavia they’ll sign up to ConvertKit, have a lot of these ideas, but they’ll never actually execute on them. And then what will happen is they’ll run into like a block or something. they’re really frustrated with some products that’s like pricing. They’re like, ‘I’m spending $1,000 a month and I’m sending one email a month, like, I’m not using the tool’. And so I can sometimes close the deal by saying, ‘Hey, I’ll migrate you over plus integrate you with, you know, best practice on a whole bunch of things’. If it’s ecommerce, or if it’s a, you know, a publishing site, I can do that. I’ll migrate and then deploy all the best practices, and then they’ll come over and then they’ll just stay there. Because most people don’t really turn email marketing, very similar to hosting.

And the other thing is also like, I’ve been building this tool since the start for myself and for my clients. And so there’s a lot of very nuanced things in the tooling that other companies can’t do, for a few reasons. Like for example, for one, when you send a broadcast in Bento, you can send him back And not just that you can pause mid batch. And one of the reasons we did that was, let’s say send an email to 100,000 people. It feels pretty good to pause a campaign after it’s gone to 100 people fix your mistake and then resume. Why hasn’t MailChimp done that, MailChimp does that little like copy thing? And then if you made a mistake, like, yeah, like it’s just gone out to everyone.

Dan: Well, we did that manually with every single campaign we’ve ever done. You send 100

Jesse: Yeah, yeah, yeah.

Dan: There’s plenty of entrepreneurs that I’ve met over the years that have just taken a piece of software like Infusionsoft or Salesforce and they just ,they SWaS it, they software with a service, and they go out and make a good living for themselves, you know, whatever their vision is for their income or their business. They do it.

I’m wondering, would it make sense for you to build an army of, you know, ‘Bento Benny’s and Belinda’s and they have insider access to everything that’s happening at the company and they just go out and implement the shit out of this.

Jesse: Yeah, I love that. But again, coming all the way back to like, ‘What the goal is for this product’. Like, I want to have a software business that I work on for the long term that I’m super stoked to work on every day. And, yeah, I’m kind of in any, any rush. So I’d like it as fun as it would have a whole bunch of people, you know, integrating bento all the time. At this stage. It’s kind of nice, the pace that we’re going, and I’ve often looked like what a larger business would look like. And I actually don’t think and again, that’s why I didn’t take the money before from the guy that reached out is because I don’t want to go faster that just yet. There’s like still a lot of things I’m feeling out. And I’m super happy where I am. And I don’t know at this stage like I feel like often in the entrepreneurial journey. Like you don’t appreciate where you are, and like the moment and I’m trying to do my best, this time around, to do that and just like go to pace I’m comfortable with and enjoy the ride.

Dan: That’s fantastic, we’re done. Thanks for coming on the show. This is amazing. And you know, Bento Now dot com Of course, Talent Tree dot io but give your give your pitch for your Twitter handle. I think people should follow you on Twitter. Because I watch the master at work here.

Jesee: We’ve got my personal profile which is at Jessie T. Hanley. And then I’ve actually got a funny story about this. I’ve also got At Bento, just the word. And do you remember the ‘Startup’ podcast? You guys did some episodes on it, remember?

Dan: Yes.

Jesse Do you remember there was a business that was documented on it called Bento?

Dan: I do not

Jesse: Okay. So there was and they got VC funding. They went under, and they listed everything on Flippa and I bought it for three and a half grand.

Dan: That’s so fantastic. You have a really cool bio, a really cool photo, you have some Japanese there to add a little flavour and maybe most notably, you are only following 654 people and 3800 people follow you. And that’s been the source of seven figures worth of deals for you. Jesse, thanks for sharing your time with us today. It was a real pleasure.

Jesse: Thanks, Dan.


Dan: Big shout out to Jesse for swinging by the show. What a wonderful talk. Jessie does what he always does, he over delivers, he shows up and shares his story in a very frank and honest way such that we might benefit from it.

And one thing I want to pull out of the conversations, we started out at the top talking about burnout, and how so many of us can feel stressed out by our creations. And a lot of that has to do with – we’re doing what other people see for us instead of sticking to our own unique vision. And sometimes that means not always going for every opportunity to grow or not always jumping for every pot of gold that someone sticks in front of you.

And you know, sometimes it’s easy to fall into that trap because that’s the right thing to do. That’s the ambitious thing to do. That’s what everybody teaches we ‘Ought to do’. And I hope one of the themes of this show over the years has been that sometimes it takes even greater ambition and vision to stick to your own. unique sense for what kind of value you want to create in the world and how you want to deliver to your customers. These things are complicated. And at the end of the day, we have to live with our own creations.

So pretty, pretty cool. A lot to think about in this one. I hope you enjoyed it. That’s it for this week. We’ll be back as always, next Thursday morning and a big shout out the team over at Smash Digital for sponsoring this week’s show. As always, we’ll be back next Thursday morning. Thanks for joining us.

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