Tropical MBA: Entrepreneurship & Founder Lifestyle

Last time Dustin Overbeck came on the show he talked about why he chose to live in Transylvania, Romania with his family whilst growing an agency and ‘Town Web’ which helps local governments in the US build and re-design their websites. Today he tells Dan about why he felt it was vital to institute structural changes to the way he worked and hire a General Manager, and about his new software business ‘Hey Gov’: “I realised Dustin is now an arsonist. But he's also a firefighter. He's creating problems that only he can solve … And sometimes you just have to step back and realise that smart people will figure out the solutions. And that's what I did.”

Today Dan talks to one of our favorite writers Sam Dogan, the man behind ‘Financial Samurai’. And Sam has recently written a book called ‘Buy This, Not That’, laying out the ideas and strategies he learnt not only from his decade long career at Goldman Sachs but also investing personally and interacting with the many millions of visitors to his blog. This week’s discussion ranges from why the traditional ‘Financial Independence, Retire Early (FIRE)’ model, of which Sam was an early pioneer, is now outdated; the reasons you can’t just ‘set and forget’ your financial planning but need to think about opitimizing it for the different decades of your life; and what it’s like to be involved in writing a book for a major publisher: “One of the reasons why I don't want to write another book is because it's so painful. A lot of cooks in the kitchen. They're all on your side, they want to make the book amazing, inclusive and a success. But I'm not used to that, I’m used to waking up at 5am writing, and then I'm done. I send it to my dad and he makes some edits. And we’re good.”

Do you remember when you had to pretend that you had a dental appointment just to be able to attend a job interview? Dan and Ian do. With so many more people working remotely, even within large corporations, those days are gone. And good riddance. But a listener emailed the show asking our thoughts about what they see as a more challenging aspect of the increasing numbers of people, especially Americans paid in dollars, now able to work from anywhere: skyrocketing rents and real estate prices in European cities like Lisbon and Barcelona, often pushing locals out. And an update from Dynamite Jobs where the team has been hard at work on an applicant tracking system (ATS) to try to help with the problem of the huge amount unsuitable applications many business owners receive when they are trying to recruit, and also a new innovation that allows users to gauge the potential number of suitable applicants for a specific role that they can expect to access when using DJ : “Our goal is to kind of demystify the results that you'll get if you post with us. I want you to know, hopefully, what you're gonna get before you post with us, especially if it's for the first time”.

The ‘post-COVID’ location independent summer is beginning. We’re seeing more and more posts in the DC forum that begin: ‘Who’s in Medellin this month?’, ‘Anyone in Poland or the Balkans’. Traveling and navigating new cities, and regions is very much the theme of today’s show, which is a discussion for those thinking of visiting Bangkok, and Thailand in general, later in the year. And, of course, we’re hugely excited for our first DCBKK event in three years, coming in October. With that in mind we’ve asked Kyla Gardner and Jesse Schoberg - both of whom have lived in Bangkok, and other places in Thailand, and attended a fair few DCBKKs - to share their thoughts. We’ll cover: where to stay in Bangkok for a great vibe and delicious food, where to consider going after DCBKK, how to manage your time around events like DCBKK, and much more: “I don't know whether to advise people to just accept that you really just have to go really hard, you’re not going to sleep, you're going to be exhausted but it's going to be worth it. Or advise them to try to take some power naps … it is just so stimulating, so much fun.”

The 4-Hour Workweek was, and continues to be, a life changing inspiration to many seeking more freedom in their lives through the path of entreprenuership. But, prompted by listening to a recent podcast featuring a conversation between its author Tim Ferriss and Cal Newport, Dan and Ian reflect on what they see as ‘the elephant in the room’ in the book, in relation to others seeking to emulate the path it lays it: “Tim is talking to people who already have a lot of enterprising know-how and other resources like industry relationships … But the book’s audience extended well beyond the well heeled and gainfully employed. It also appealed to those of us who didn't have businesses, established cash flows, or other traditional advantages”. And this episode also includes responses to a related question posed by a listener, one that often pops up in the TMBA mailbag: how to have an impactful career as a solopreneur.

Today’s guest, Sherry Walling, is a respected clinical psychologist who specialises in entrepreneur mental health. She’s also the host of Zen Founder, a podcast where she is sometimes joined by her husband Rob. Those who have listened to Zen Founder know that Sherry has been sharing movingly about the upheavals and losses she’s gone through over the last few years - in 2018 she lost her father to cancer followed, six months later, by her brother to suicide - and how it's affected her, and their whole family. On today’s show Sherry talks to Dan about how she tried, in some way, to make sense of what happened by penning a book “Touching Two Worlds: A Guide To Finding Hope In The Aftermath of Loss” “The events of the past few years have been so strange to me that I must force myself to study the story, like something I am learning from the outside in, like something that happened to someone else ”. It’s a moving account of what she discovered, including some great practical suggestions for others finding themselves in a similar place and struggling to cope. In Sherry’s case this included joining the circus (evenings and weekends only).

Unless you’ve been living in a cave recently (and if you have, hit us up because we’d love to hear about that), you’ll be aware that crypto has been on a wild (at the time of writing mostly downward) rollercoaster. As we’ve mentioned before, it is a volatile investment, especially when viewed short term. But today’s show isn’t about that. It’s about how crypto can be - *insert an important ‘health warning’ here: this is not advice, it’s just thoughts and views - a practical way to fund other things, like buying a house, and even be set to be a relatively low ‘management threshold’ investment, as today’s guest did when she had a baby. Cathryn Lavery is well known in the entrepreneurial community as the CEO of Best Self which produces stylish and imaginative planning, goal setting and relationship journals. She talks to Dan about how a painful business break up, in part, lead her to create a practical course for those who want to learn more about investing in crypto, called ‘Zero to DeFi’: “It was such an emotional drain for me. The crypto stuff, just learning about it and getting into it, was something exciting for me … I didn't even talk publicly about crypto. Because there's this vibe of scammy. Like how do you go from Best Self to talking about crypto …And then, at the end, I was like: screw it I'm just gonna start talking about this stuff. Because I think, as entrepreneurs, we get interested in different stuff. And so if I'm excited about working on something, then hopefully other people are excited about it as well”.

On today’s show Dan and Ian are reaching into the mailbag to reflect on some topics that listeners have asked about. These include an update on the incredible response to our upcoming DCBKK, things to consider when thinking about business models, and how to manage your net worth without hurting your brain: “I have been guilty in the past of overcomplicating my financial process with too many credit cards, too many bank accounts, too many clever tax manoeuvres, and I would have been much better off to keep it super, super simple’.

Today’s show challenges bootstrapped entrepreneurs to think about lessons they can draw from high-income private equity funded business, especially about structured forward planning and accountancy. But it also covers what lessons PE funded companies could learn from the other side of the tracks. This week’s guest is Jason Long, a valued member of the DC community, well known for being always open to sharing the highs and lows of his long experience of founding agencies, creating Software as a Service businesses and, most recently, from accepting a job as a ‘turnaround CEO’ for a private equity group. He talks to Dan about how the devastating effects on his agency of the 2008 financial crash caused him to diversify his portfolio, and the pros and cons of that decision. Plus why working with a multimillion PE firm has enhanced his experience both as a leader and entrepreneur: “This is a team that had been passed from CEO to CEO, from leader to leader, who just had failed them over and over and over again .. And so when I came in, I said, ‘I’m not gonna I'm not gonna fire anybody’ .. And I brought in a lot of methods to make sure that there was transparency with the top level all the way down to the frontline workers .. so everybody felt like they were knowledgeable about where the company was going. And I felt like that made a huge difference in the trust”.

Lots of entrepreneurs and listeners to this show are inspired to create ‘The 4-Hour Workweek’ type businesses by founding e-commerce stores and agencies, creating money and value entirely online. Today’s guest, Alex Pantich, has chosen a different path with the business he co-founded. Upshift provides hospitality venues with vetted temporary W-2 hourly workers who are able post online the days and hours they are available for work. Alex talks to Dan about how this double-sided marketplace works, the equity share scheme Upshift deploys, and why he thinks so many entrepreneurs are missing out by not considering blue-collar, location dependent opportunities: “When you're getting online and into E-commerce, you're competing with your peers. If you go into the real world, you're competing with baby boomers. Are you telling me the baby boomer who doesn't know email is going to beat you at any sort of innovative business game? They're not. I prefer going into areas where I see tonnes of opportunity and not as much competition”.