On this week’s show Jeff Fruhwirth talks to Dan about how a failed foray into e-commerce, and a change in personal circumstances, caused him to pivot into real estate investing with little capital or experience. Today he has a portfolio of multi-unit buildings, which he’s expanded by learning about the hidden potential within different sorts of properties: “One of the best ways to make money is to kind of take on deals that no one else wants to touch. I looked at a building last summer that had been hanging on the market for quite a while. And the main issue was .. there was a five unit apartment building and a two bedroom house, but they were on the same tax lot and share the same water tap. So there was plenty of money in there, as long as you are willing to pay to dig up the water and sewer line, and then pay the $13,000 to the water utility to get the water metres separated … then you could sell off the house, you could fix up the apartments, and functionally double the rent”. Jeff also shares some inside stories and insights from the very first DSki, which took place in Steamboat Springs, Colorado.

This week Dan and Ian share updates about progress at ‘Dynamite Jobs’. Drawing on some sage advice from recent guest Ayman Al-Abdullah, they’ve been focussing on the ‘P’s that really matter, namely breaking through plateaus by building strong foundations through ‘product, promotion and process’. The idea being that will enable them to move on to the next stage in their business, from ‘player to coach’: “One of the points that Ayman made is, ‘Look, you are the last star player, you're ever going to get on a rookie contract’, everyone else is going to work less hard than you, is going to care less, and is going to demand more money”… So when you're ready to pick up the clipboard, you have to have a rock solid legacy in place in terms of product, promotion, process and people … And now all of a sudden, we're not jumping the gun. I want to flag this up because I see a lot of people trying to get to that mid eight figure seven figure business by jumping the gun on bringing in the executives that are kind of doomed to failure, because there's no clarity on how the business will grow”. And stay tuned to the end to hear Dan and Ian’s thoughts about resume gaps and ways to fill them.

The last time Allen Walton was on the show he talked about the origins of his e-commerce business SpyGuy grew out of a difficult period when he was living in his parents’ basement struggling to make a living. Today Allen talks to Dan about some of the challenges he’s had which, despite the considerable success, has caused him to consider if it’s time to re-orientate what he’s doing and focus more on his new venture FlyGuy: “Spy Guy is a hard business to run. Like a lot of e-commerce businesses we've been facing supply chain problems, shipping shortages, our costs have really gone up … And I think about Tony Hsieh’s book ‘Delivering Happiness’, he talks about poker playing, and how you could sit at a table and you might just keep losing, losing, losing against the people you're playing with. One of the best things you might do is just get up and move over to another table. You might find out that you're playing way better there. And I kind of feel like that might be the case for me”. And, later in the show, Allen gamely agrees to play our favorite fun challenge: ‘Donate A Business Idea’.

One of the biggest challenges we discuss on the show is how to take businesses over the “five figure” hurdle. Today’s guest Ayman Al-Abdullah has done that in his time as former CEO at AppSumo, and he shares his major takes on achieving that with Dan. “You're essentially crafting your rock band. What more important job than who I'm hanging out with on a daily basis and hanging in the tour van, I think the most important job of the CEO is: ‘Who is in the van?”

On today’s show, GrowthHit’s Jim Huffman talks to Dan about the pros and cons of running a successful agency, and how he’s recently been encouraging and enabling his team to create new products via an internal ‘startup studio incubator’. Interestingly, he’s done this, in part, to incentivise people, and offer a creative and rewarding work environment in this increasing competitive job market: “It’s potentially a path to allow really good team players and employees to make their own decisions and part carve their own path within a company, maybe without taking on some of that initial risk .. how can you create this hybrid that meets those people where they're like, ‘Hey, I want to work remote, I want to like do my own thing, but I'm down to have this structure’. It's like, ‘Ok, we need the agency work to get done. But we have a budget to allocate if you have a good idea and if that becomes something, then you have a significant stake in it.”

‘Side hustles’ are a long running theme on this show: those ‘weekends and evenings’ projects that many entrepreneurs have in their back pockets. Many don’t work out but when one does, it’s a great opportunity to run with something which has the possibility to evolve to the next level. But how do you decide when that tipping point is? In today’s show Ben Dowling joins Dan to describe how coding a simple API, to solve a problem he was experiencing while working as the CTO of Calm, lead him to found a Software as a Service called IPinfo, which create datasets about IP addresses: “So many projects I shipped .. felt sort of uphill pushes. And some of them had some moderate success, but it was always an effort. Whereas IPinfo, the traction was sort of straightaway .. And so I think if people are struggling with a project, ‘Hey, do I just need to keep working hard on it?’ It may be best to try something different .. I had no expectations for IPinfo .. but it very quickly sort of started going in that direction”.

Back by popular demand, Dan and Kyla Gardner blow the dust off their bookshelves, and fire up their Kindle and Audible libraries to share some of their favorite recent reads. In this episode, they’ll be talking about what sustained them through the long months of COVID containment. And Kyla also shares her experiences of writing fiction under her pen name Kyla Sharp. “There are so many people making so much money from fiction. Obviously, anyone can self publish, so it has a bad rap and there's a lot of junk out there. But sometimes you can't tell the quality difference because people hire professional editors, they get professional cover designers. They run it through their readers to make sure everything makes sense and they don't have typos. And then they self publish it and they get 70% of those royalties from Amazon instead of traditional publishing where you have to pay back your advance and you might be getting something like 5%”.

Affiliate Marketing businesses have been around way longer than this podcast, and it’s a model that receives its fair share of criticism, especially of those selling ‘courses on how to sell courses’ on the subject. However, one thing is for sure: thousands of entrepreneurs continue to support their families from income generated by affiliate marketing. On today’s show Dan talks with Niche Site Project’s Doug Cunnington about how the model has changed since the early 2000s, ways to seek out good niches and why, even if affiliate marketing isn’t your end-goal, it can be a great place to start: “For example, if you start a niche site, and you're not sure if it's going to work out .. you learn about setting up a website, you learn about keyword research .. and all these different skills that can be really helpful in the future. You may figure out that you're really good at hiring writers, and managing them. And that could turn into a whole different business.”

The ‘AntiWork Movement’ has been with us for decades but, through the pandemic, it’s gained a new traction over at the online discussion forum ‘Reddit’, where the r/antiwork subreddit group (slogan: “Unemployment for all, not just the rich!”) has over 1.7 million subscribers. Just recently, a controversial media interview by one of the moderators caused the thread to be temporarily locked. Today Dan and Ian discuss why, in some ways, they’re sympathetic to some of the AntiWork Movement’s points but not necessary the ways they go about addressing them: “We have a lot of the same founding premises, maybe in 2007/2008 timeframe, we'd say, ‘Hey, we're gonna quit our jobs and start a lifestyle business because we don't want to be subjected to the poor outcomes, and the poor treatment, a lot of the American workforce sees. But also, we saw a changing tide in technology and globalisation, and a necessity to employ a new strategy to be able to achieve wealth and freedom in this new environment”.

Tiny Seed co-founder Rob Walling joins Dan to share insights about why bootstrapped businesses, particularly Software as a Service (SaaS), are becoming increasingly desirable to investors, partly due to the ‘downside protection’ they offer. They also discuss the pros and cons of serving ‘two sided marketplaces’ and why Rob has recently updated his ‘Stair Step Approach’ to entrepreneurship: “One thing that has changed is that there are a lot more opportunities to do ‘step one’ businesses that are recurring revenue from the start, like Shopify add ons .. If there's already a marketplace in place, it takes a huge amount of complexity off your plate .. it allows you to build the business and then learn the other stuff as you go.”