Other Playbook

Upshift is a double-sided marketplace connecting hospitality venues with vetted temporary W-2 hourly workers. Co-founder Alex Pantich deliberately chose to build in the blue-collar, location-dependent space rather than competing in crowded e-commerce and SaaS markets, arguing that traditional operators lack the digital sophistication to compete effectively.

Allen Walton, founder of the e-commerce business SpyGuy, is transitioning to a new venture called FlyGuy after facing significant challenges in e-commerce including supply chain disruptions, shipping shortages, and rising costs. Inspired by Tony Hsieh's philosophy of moving to a better opportunity when circumstances aren't favorable, Allen is exploring this new direction while reflecting on his business journey.

GrowthHit is a successful agency run by Jim Huffman that has recently implemented an internal 'startup studio incubator' model to encourage team members to create and develop new products. This hybrid approach allows employees to maintain agency work while pursuing entrepreneurial ventures, offering them equity stakes in successful products as a retention and motivation strategy in a competitive job market.

Brian Casel transitioned from running Audience Ops, a productized service, to building ZipMessage, a SaaS product. He discusses the fundamental differences between the two business models—productized services rely heavily on repeatable processes, while SaaS requires continuous feature development and marketing channel experimentation. This time around, Casel decided to take funding after previously bootstrapping and selling Audience Ops without a broker.

Jodie Cook built a social media consultancy agency designed as a lifestyle business around her name, allowing her to balance entrepreneurship with her career as a competitive powerlifter representing the UK internationally. The business achieved a successful exit with no earnout period required, demonstrating strong fundamentals and the ability to scale beyond a personal brand dependency.

CruiseSheet is a website created by Tynan, a bestselling author and unconventional entrepreneur, that helps travelers find great deals on cruises. The source provides minimal information about the product's traction, revenue, or growth metrics.

MaidThis is a residential and Airbnb cleaning service company founded by Neel Parekh. The company has implemented a customized version of the EOS (Entrepreneurial Operating System) framework to manage team growth and operations with impressive results.

Greenback Expat Tax Services, co-founded by Carrie McKeegan and her husband Dave, helps Americans living abroad prepare and file their taxes. The company emerged from the McKeegans' personal experience raising their children as "Third Culture Kids" outside the United States, with Carrie using the Covid pandemic as an opportunity to reinvent her family's educational approach while building the business.

DropInBlog is a SaaS platform co-founded by Jesse Schoberg. The company appears to be bootstrapped, with the founder discussing location arbitrage and financial freedom in the context of the permanent travel lifestyle.

Mythia is a financial startup co-founded by Derek Pankaew that partners with banks to offer a debit card exclusively for gamers. The company has raised approximately $2.2 million in venture capital funding. Derek's entrepreneurial journey spans from bootstrapped passive income businesses to venture-backed startups in San Francisco.

TouchMBA is a service founded by Darren Joe that matches prospective students with MBA programs. Darren operates as a solopreneur and has authored a book called 'The Fail-Safe Solopreneur' based on his experiences navigating entrepreneurship independently.

Nick Huber pivoted from Storage Squad, a student storage company decimated by COVID-19, into Bolt Storage, a multi-million dollar real estate private equity company. He leverages Twitter to find investors and has built significant traction in the real estate space through strategic pivoting and rapid decision-making during the pandemic.

CrewFire is a brand ambassador and influencer management platform founded by Alan VanToai, a non-technical founder who has successfully created and exited multiple software ventures without coding expertise. The company operates as a SaaS business focused on helping brands manage their influencer and ambassador relationships.

Objection.co is a SaaS business founded by Curtis Boyd to identify and dispute fake reviews on the internet. Curtis started by disputing a single review for a client and evolved the concept into a software platform addressing a multi-million dollar industry of online review manipulation. The business grew out of Curtis's expertise in review authenticity and his decision to study artificial intelligence to better combat fake reviewers.

ZenMaid is a niche scheduling software for maid services founded in 2013 by Amar Ghose. Born from the failure of Amar's own maid services company, the product pivoted to serve the industry he learned from firsthand. Amar has applied digital marketing strategies to the blue-collar maid services industry with his software solution.

ShipHero is a remote company offering outsourced shipping fulfillment services and warehouse management software to eCommerce businesses. Founded by Aaron Rubin, a veteran of the eCommerce space, the company was born from his frustration with high shipping costs in his own business. Today, more than 1 in every 200 eCommerce packages delivered in America are shipped through ShipHero.

HubSnacks is a productized service founded by Ian Horley that offers unlimited tasks on the HubSpot platform for a fixed monthly fee. After leaving corporate in 2014 to start a web agency, Ian struggled with the stress of agency work and pivoted to productizing his HubSpot expertise. The business represents a shift toward systems-driven operations and community-focused growth.

MostlyStories.com is a content platform founded by Jeff Pecaro, a talented copywriter. The company is known for creating content for Dynamite Circle's in-person events, including their annual DC BKK gathering in Bangkok.

Simon Payne is a serial software founder who served as technical co-founder of Leadpages before launching multiple ventures including Convert Player (a video tool) and EventsFrame (a ticketing tool). His entrepreneurial journey has yielded mixed results, and he is now focusing on helping build software platforms at Dynamite Jobs while discussing the critical relationship between developers and marketers in software business success.

Caravan Digital is a digital marketing agency founded by Eagan Heath that serves eCommerce businesses. The company represents a strategic pivot from his previous approach of serving local businesses by filling knowledge gaps, instead focusing on filling 'efficiency gaps' by optimizing marketing services already being used by online retailers.