Brynn Michelich, Chief of Staff at Chicago-based Jellyvision, joins Scott to talk about the panic surrounding COVID-19's impact on businesses everywhere, what Jellyvision has had to change and what they haven't, how to maintain and improve team culture and keeping the team productive in our new normal.

John Green and the team at Nada wants to make you CEO of your largest asset: your home. Nada simplifies the home ownership buying and selling process by handling mortgage, title and insurance services while eliminating realtor fees. John joins Scott on the show to talk about how his background as punk rock musician helped shape his career as a strategist, understanding the problems in the real estate market, how to test product-market-fit and putting more equity in homeowners pockets.

Jason Fried, founder and CEO of Basecamp and HEY Email, joins the show to talk with Scott about the future of email, why it's gotten mucked up and why bringing privacy back into our lives is a correction long overdue.

Albert Baez, co-founder of Blended Sense, joins the show to talk with Scott about the missing infrastructure small businesses need to succeed digitally and drive revenue. Blended Sense is a platform and content management system for production communication, project management, and delivery of high quality assets. Using a subscription model, Albert and his cofounder, Abigail, provide a centralized marketplace for business owners to fulfill needs and source creative talent locally, who are matched on projects automatically based on project needs and receive steady work.

Gaming has been a part of Ben Goldhaber's life since he started as a competitive player in his teens. He's stayed in the industry ever since, and after his experience as part of the founding team at Twitch through the Amazon acquisition, he saw firsthand the broad market opportunity, exponential growth in the gaming industry and most importantly saw what was missing: a centralized platform to get the best information on all things Esports. That's the engine behind his startup Juked, which Scott likes to compare to the Bleacher Report-for sports. Ben joins the the show to talk about how he came up with the idea, how the model works, monetization strategies, the rapid esports transition into the mainstream, gambling, and how you can invest in the company today through their crowdfunding campaign on Republic.

You've heard the stories about WeWork. The private jet parties, the billions of investment and unfathomable $47 billion valuation. What you don't hear is the the back story behind the man that started it all, Adam Neumann. Reeves Wiedeman, NY Mag writer who penned their feature article detailing the behind the scenes work of Adam, goes into full detail in his biography "Billion Dollar Loser: The Epic Rise and Fall of WeWork". Reeves joins Scott on the show to discuss the business fallout from the failed IPO, who Adam really is, lessons in entrepreneurship and why the best intentions can still mask a graver reality.

Securities aren't as dependable as they used to be, and with alternative assets like crypto, crowdfunding, PE, etc growing in popularity, future retirees aren't reaping the benefits like previous generations could from stocks. Eric Satz, founder and CEO of AltoIRA, joins the show to talk about retirement investing, why it's changing and what individuals need to do to diversify their investments and be actually able to retire comfortably.

Pillar Booth creates ventilated, soundproof desk spaces that give you a safe space to avoid distraction. Ryan Leavitt, a repeat founder previously of LearnCore (acquired by Showpad) and Catapult Chicago, shares his long entrepreneurial journey and how the shift towards open office spaces leaves employees with no place to take a phone call in private and generally diminishes productivity. The booth allows workers to focus better on specific tasks, make calls and with the slow return to the office, a safe place to get things done.

Whether you work remotely or in an office, you're no stranger to the overload of project management apps your company has you use in the name of productivity. Slack, Asana, Microsoft Teams, Google Drive, Notion- all have their pros and cons, but how do they all work togethers across different company departments? That's the question Jonathan Friedman set out to solve when he founded TrueNxus, a platform that shows how work is being done against the greater project plan, and tracks results with visual predictive analytics. Jonathan talks to Scott about taking an overview look at a business and how teams work together, his background and how to stay out of Google Sheets and Powerpoint hell.

When COVID-19 put the office workers at home indefinitely, Thru Shivakumar thought her company would be dead in the water. However as the dust began to clear (working professionals and parents struggling to work from home),it's evident offices have a place in the current work environment. Cohesion empowers real estate owners to maximize asset and portfolio value with all building systems, workflows and people seamlessly connected in one intelligent building platform. Thru joins the show to talk about the future of the workplace environment, how Cohesion uses IoT to make office systems more efficient, employees safer and more comfortable.