Tropical MBA: Entrepreneurship & Founder Lifestyle

Even though 2020 has been a difficult year for some entrepreneurs, it has arguably been an all-time year for many people running eCommerce businesses. Longtime listeners know that we first cut our teeth in the eCommerce space, and we love keeping tabs on how that industry continues to evolve and innovate. It's no surprise then that today's guest made his way onto our radar. Aaron Rubin is a longtime veteran of eCommerce. Aaron's growing annoyance with the shipping costs related to his business drove him to create ShipHero, a remote company that offers outsourced shipping fulfillment services and warehouse management software to other eCommerce businesses. Today, more than 1 in every 200 eCommerce packages delivered in America are shipped through ShipHero. Aaron joins us today to share his story. You'll hear how his first eCommerce business nearly went bankrupt, how a need to "scratch his own itch" led to the creation of ShipHero, and Aaron's somewhat insider take on where the eCommerce industry is headed in the future.

We are reaching back into the mailbag this week to answer questions submitted by Tropical MBA listeners around the world. In this edition, we'll be focusing on three specific questions that we believe get to the core of what it means to be resilient as an entrepreneur. We'll be discussing how much money you should save as a "runway" if you plan on leaving your job, the fundamental differences between hiring freelancers and hiring employees, and how you can navigate questionable business advice on the internet. You'll also hear an update about the new products that we are launching over at Dynamite Jobs, and why we are somewhat optimistic about events returning in 2021.

This week's episode is about something that is incredibly near and dear to our hearts: personal blogging and what it means to write on the internet. To help us tell this story, we've invited two of our favorite writers who both have a long and rich experience in the blogging space. Taylor Pearson has been a frequent guest and contributor on this podcast. He is the author of The End of Jobs, and he runs an excellent blog over at TaylorPearson.me that has been required reading for us for quite some time. Amanda Cook is an author, a podcaster, herbalist, and the founder of a business called Wellpreneur. Over the years, she has published online about a wide variety of projects, but the one consistent thing is that she's always had an excellent blog, which you can find at AmandaCook.me. Join us for this round table discussion about the past and future of blogging on the internet, tips for those starting out with a personal blog, some of our favorite blogs to read today, and so much more.

We've been receiving a ton of requests recently from listeners who want to hear an "old school" episode, so this week Dan and Ian are jumping on the horn to talk about the progress that they've made with their remote jobs business Dynamite Jobs. Since the start of the summer, we've been building a new software platform designed to make the hiring process a whole lot easier for entrepreneurs. Just a few weeks ago, we finally started onboarding users into the platform. So far the results have been remarkable, but the challenges immense. In today's episode, we're sharing four specific things that we've learned from creating a brand new software product. You'll hear updates about some key figures in our business, how running a SaaS business has differed from a lot of our other ventures, and a whole lot more.

For our money, there is nobody quite like Kevin Kelly. Not only is he one of the co-founders of Wired Magazine, but he is also the author of some of our favorite pieces of writing about technology, including What Technology Wants, New Rules for the New Economy, and the brilliant essay 1,000 True Fans, which has been discussed countless times on this show over the years. This week, Kevin is joining us for a conversation about technology and how it informs our lives and businesses. On this podcast, Kevin shares his thoughts about why we have to stretch our imaginations more, what we can learn about technology from the Amish, why you should focus on "Being the only", and so much more.

Today's podcast is all about one listener of this show who took the concept of productizing and applied it incredibly well at a very high velocity. More than that, it's a story about endurance, applying systems intelligently, and the power of community. Ian Horley left a long stint at a successful corporate job in 2014 to create his own web agency, but he ultimately found himself incredibly stressed and unhappy. Today, Ian is the founder of HubSnacks, a productized service which offers unlimited tasks on the HubSpot platform for a fixed monthly fee. In this week's episode, Ian joins us to recall his tale of leaving the corporate world, why he struggled with the day-to-day of running an agency, and how productizing has finally allowed him the freedom to create a business on his own terms.

Longtime listeners know that this is typically the time of year that we host DC BKK, our annual Dynamite Circle event in Bangkok. Each year, hundreds of entrepreneurs flock to the capital city of Thailand for the chance to meet and share ideas with like-minded people from across the globe. This has always been sort of a magical time for so many of us in the community, and to say that we are disappointed that we can't take part in it this year would be a huge understatement. It has become something of a tradition that our good friend Jeff Pecaro sits down with us after the event to crack open a beer and talk shop. Jeff is an incredibly talented copywriter and the founder of MostlyStories.com. He is also the man behind the content at most of our in-person events. This year, Jeff is joining us virtually on the podcast to commiserate and share some of our favorite memories, thoughts, and insights into the history of DCBKK.

Greg Gerber, a cryptocurrency expert known for making complex topics accessible, joins the discussion on the current state of crypto. He delves into the philosophical distinctions between Bitcoin and Ethereum, shedding light on their roles in transactions and investments. The conversation highlights the burgeoning crypto lending market and potential passive income opportunities. Greg also shares insights on his new venture, BitLift, aimed at helping entrepreneurs navigate the evolving landscape of digital currencies.

We've been devoting a lot of time to talking about software businesses in recent weeks. One of the reasons we are so fascinated by them is that despite how difficult it can be to start one, these types of businesses can have tremendous upside. Jordan Gal is the founder of CartHook, a software company that helps Shopify merchants present offers to shoppers at checkout. Jordan first reached out to us back in 2015 with an investment opportunity (and we turned him down!). It really shouldn't come as a surprise then that Carthook has grown exponentially in the years since, with its user base having made more than a billion dollars worth of sales. Jordan joins us on today's podcast to share the story of CartHook.

Today's episode is all about software startups, and there are very few people more capable or qualified to talk about them than today's guest. Simon Payne first joined us on this podcast back in 2016 to talk about his role as the technical co-founder of Leadpages. Since leaving Leadpages in 2016, Simon has gone on to found multiple software companies, including a video tool called Convert Player, and a ticketing tool that we regularly use in our own business called EventsFrame. But, as you will hear on today's podcast, the results of these endeavors have ultimately been a mixed bag.  Simon joins us this week to share the details of his entrepreneurial journey over the last few years, to discuss how the relationships between developers and marketers can make or break a software business, and to explain why he's recently decided to help us build our own software platform at Dynamite Jobs.