That Will Never Work

Diego Chavez, founder of the Local Contact travel-support app, shares his journey through startup burnout and the intense pressures that led to personal crises. He emphasizes the need for founders to prioritize mental health and the benefits of taking time off and seeking therapy. Therapist Susan Zinn provides evidence-based strategies for managing stress and discusses the stigma of mental health in startup culture. They explore the importance of honest communication with investors and advocate for reassessing growth goals to ensure well-being.

Karl is faced with a puzzling subscription problem: he has plenty of downloads of his Cofeesup app – but his conversion rate from free trial to paying customer is surprisingly low.  His solution to lift up neighborhood cafes over the mega marketers like Starbucks seems like a no brainer – you can get three cups of specialty coffee a week for just $8 a month… and the cafes even get supplied with free beans.  So why isn’t his growth as caffeinated as his product?Listen in as Marc takes Karl on a back to brass tacks masterclass in how to understand customer behavior… and then goes on to tackle another entrepreneurial biggy… How does Karl know when it’s time to let go of being the CEO?This episode is so jam packed with advice you won’t want to miss it! Want to take a deeper dive? Pre-order the paperback edition of international best-seller That Will Never work here: www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530182 It’s out June 7th. Want to be a guest on That Will Never Work? Head to marcrandolph.com/guest to apply.  While you’re there, sign up for Marc’s newsletter: marcrandolph.com/newsletter/Feeling social? Marc would love to hear from you:Tw: @mbrandolphIG: @ThatWillNeverWork LinkedIn: Marcrandolph  

Is the old adage still true, that it takes money to make money?  That’s what this week’s guests Lauren Arshad and Jen Cefaly are trying to figure out.They are the co-founders of Los Angeles based Design Hive, an edutainment company that creates hands-on STEAM workshops for both kids and adults. The duo are brim full of ideas and are poised to grow but both they - and their capital - are spread thin… Is it the right time to raise?Listen in as Marc dissects predicaments faced by every early stage entrepreneur… and gives tips on how to find your business sweet spot.Want to take a deeper dive into the topics on this show? Pre-order the paperback edition of international best-seller That Will Never work here for delivery June 7th. www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530182 Want to be a guest on That Will Never Work? Head to marcrandolph.com/guest to apply.  While you’re there, sign up for Marc’s newsletter: marcrandolph.com/newsletter/Feeling social? Marc would love to hear from you:Tw: @mbrandolphIG: @ThatWillNeverWork LinkedIn: Marcrandolph   Tiktok: @marc_randolph

Paul Bennett, founder of Cicero Learning, shares his journey into world schooling and the challenges of providing bespoke remote tutoring solutions. He discusses the unique blend of tutors at Cicero, including retirees and remote educators. The conversation dives into effective sampling strategies to attract customers, highlighting the success of free trial classes. Marc offers insights on tiering services to expand the client funnel and emphasizes the importance of becoming an authority in remote education through content creation.

In this discussion, Josh Cliffords, founder of FreeWater, shares his vision of creating ad-backed, free consumable products. He talks about his nonprofit origins and his ambitious goal of launching the world’s first free supermarket. Josh explains how FreeWater uses packaging as ad space, tying in charitable giving with profits. They also dive into the challenges of advertiser ROI and the impact of his viral TikTok success on brand awareness. Can he prove the model works and transform consumer shopping? Tune in to find out!

It’s no secret that the pandemic hammered small businesses - especially those with brick and mortar locations.  But this week’s guest, Angela, wasn’t going to let her thriving math enrichment business close, even when her store had to. As a prime example of the power of the pivot, she’s actually managed to more than double her customer base and take her Philadelphia local business Trapezium Math, national by moving it online... But all this potential for growth has her at a crossroads - should she keep going slow and steady or is the time ripe to raise funds and expand even faster?   And can she compete with the big franchise players like Mathnasium and Kumon?That’s what Marc’s here to help her figure out today… Want to be a guest on That Will Never Work? Head to https://marcrandolph.com/guest (https://marcrandolph.com/guest), fill out the form and record the question you’d like Marc’s help with right there on the site. And while you’re there sign up for Marc’s newsletter https://marcrandolph.com/newsletter/Feeling social? Marc would love to hear from you:Tw: @mbrandolphIG: @ThatWillNeverWork LinkedIn: Marcrandolph   Tiktok: @marc_randolph

She’s worked with celebrities like Kendall and Kylie Jenner, brands like Adidas and magazines including Rolling Stone and Teen Vogue… She's even been a judge on Miss USA.   But fashion photographer Sophie Elgort has hit a career juncture faced by many would-be entrepreneurs: how do you scale when your business is you?She thinks she’s created a solution in her new company ClickHouse, which does  back-to-back portrait photography pop up sessions to create “headshots” - photos that people use of themselves for business purposes.  Her vision is to emulate the success of blow-dry salon Dry Bar and create a repeatable, scalable business that she can replicate all across the US.  She’s had success with her New York local pop up studios, but to make real money she needs to get some big businesses on board to give her the volume of people needed to keep with her vision of keeping the costs affordable but still being able to generate enough revenue for her company to be a success. Listen in for some great tips on how to find your scalability sweet spot, as Marc discusses her options in approaching the next phase in her business evolution and even gets some tips on his own headshot in the process.New episodes every Tuesday. Want to be a guest on That Will Never Work? Head to https://marcrandolph.com/guest (https://marcrandolph.com/guest), fill out the form and record the question you’d like Marc’s help with right there on the site. And while you’re there sign up for Marc’s newsletter https://marcrandolph.com/newsletter/Feeling social? Marc would love to hear from you here:Twitter: @mbrandolphInstagram: @ThatWillNeverWork LinkedIn: Marcrandolph   Tiktok: @marc_randolph

Army vet Cooper is the founder of SoBet, a new peer-to-peer sports betting and social media platform that targets the elusive Gen-Z consumer.   But it’s a pitch that Marc has heard a thousand times before… and most of those pitches failed to make it.  Can this West Point grad prove both to Marc - and to the market - that his mix of reducing the juice and onboarding influencers is enough to get his platform off the ground?Listen in for Marc’s tips for trying to find success in a crowded market.  Want to be a guest on That Will Never Work? Head to https://marcrandolph.com/guest (https://marcrandolph.com/guest), fill out the form and record the question you’d like Marc’s help with right there on the site. And while you’re there sign up for Marc’s newsletter https://marcrandolph.com/newsletter/Feeling social? Marc would love to hear from you:Tw: @mbrandolphIG: @ThatWillNeverWork LinkedIn: Marcrandolph   Tiktok: @marc_randolph

How do you support entrepreneurial spirit in your child?  That’s what Marc explores in this week’s episode with the help of the first ever quartet of co-founders to appear on the show.  Elementary schoolers Julianne, Zachary, Maxfield and Mark have created beverage brand Astronade and caught Marc’s attention with their plucky marketing plan that even wound in their local mayor.   Could the kid factor be the secret sauce?  Listen as Marc gives a masterclass in how the youngest of entrepreneurs can get on the launch pad to success. Want to be a guest on That Will Never Work? Head to https://marcrandolph.com/guest (https://marcrandolph.com/guest), fill out the form and record the question you’d like Marc’s help with right there on the site. And while you’re there sign up for Marc’s newsletter https://marcrandolph.com/newsletter/Feeling social? Marc would love to hear from you:Tw: @mbrandolphIG: @ThatWillNeverWork LinkedIn: Marcrandolph   Tiktok: @marc_randolph

James Kostrichan, a professional adventurer and founder of My Adventure Group, shares insights on transforming thrilling expeditions into corporate team-building experiences. He discusses the challenge of communicating the value of his unique programs, aimed at high-profile clients like Rolex and Ferrari. Marc helps him reimagine his offering to attract more customers by suggesting a tiered system that includes lower-commitment options. Their conversation explores the surprising mental shifts wilderness experiences can inspire in participants.