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Episode 287: Sam Rosen – Coworking Space Pioneer, Co-Founder of Deskpass

Sam Rosen, the Co-Founder and CEO of Deskpass, joins the show to share his journey from starting a rollerblading delivery service growing up to making coworking spaces easier to reserve than ever. Hear how he started the first coworking space in Chicago, the most creative coworking spaces, how to manage thousands of customers, his favorite lessons from his creative parents, and the best things to do in the Chicago River. This episode covers everything from beat poetry to Grace and Frankie. Here’s a small sample of what you will hear in this episode:

• What other businesses did Sam start growing up
• Pure Truth: New Edition by Sam Rosen
• What were the early days of coworking like
• How do you start a coworking space
• Thumbs up!
• What’s the story behind Sam’s mom’s paintings
• That’s why you ask 1 question at a time, Max
• A triple entendre

Connect with Sam at SammyRosen.com and Deskpass.com.

Enjoy the shoooooow! Check out the show notes below for much more detail. You can also find the full transcript here.

Show Notes

• Intro & Serial Entrepreneurship
  • [0:35] Email me at max@maxpodcasting.com to save time with your high-quality podcast and use it as a business-building tool
  • [0:45] Connect with Sam at SammyRosen.com and Deskpass.com
  • [2:15] Shoutout, the Rozens!
  • [2:39] What was Sam’s rollerblading delivery service
  • [3:14] Lincolnwood, IL
  • [3:31] Uber
  • [3:52] Why didn’t that business work out
  • [4:20] Beverly Hills Cop (wrong reference)
  • [4:45] LEGO
  • [5:02] What other businesses did Sam start growing up
  • [5:18] Pure Truth by Sam Rosen
  • [5:54] Pure Truth: New Edition by Sam Rosen
  • [6:07] Healing Earth Resources
  • [6:11] Fender Sunburst Guitar (Starburst)
  • [6:27] How did Sam get into beat poetry

• The Deskpass Story
  • [7:51] What were the early days of coworking like
  • [8:01] The Coop
  • [8:07] One Design Company
  • [8:50] Wi-Fi, Latency, Soundproofing
  • [9:41] Millennial, Entrepreneur
  • [9:51] Rabbithole
  • [10:01] Internet
  • [10:32] Shoutout, Noah!
  • [10:41] What is Coworking
  • [11:02] The Change You Want to See
  • [12:45] Oh boy
  • [13:24] Podcast Guests
  • [13:31] Google, Wikipedia
  • [13:42] How do you start a coworking space
  • [14:01] Charles Adler, Kickstarter, Ryan Graves, James Bond
  • [14:09] Ha!
  • [15:20] Where did the idea for Deskpass come from
  • [16:18] Math!
  • [16:54] Great question
  • [17:25] Deskpass Website
  • [17:59] How do most people use Deskpass today
  • [18:18] Adoption Curve
  • [18:38] TRONCH
  • [19:46] Shoutout, Judy!
  • [20:24] What are some well-known Deskpass clients
  • [20:43] Synchrony Financial, GoodRx, GSA (General Services Administration), USGS (United States Geological Survey)
  • [21:10] What does ICP mean (Ideal Customer Profile)
  • [21:40] How do you attract new customers
  • [22:30] The Lightswitch Analogy
  • [22:38] Thumbs up! (see above)
  • [22:50] Metaverse
  • [24:21] How do you manage thousands of coworking spaces
  • [24:57] Technology (Tech)
  • [25:02] That’s why you ask 1 question at a time, Max
  • [25:32] How does Deskpass find coworking spaces
  • [25:52] Shoutout, H’boken! (Hoboken)
  • [26:42] Industrious
  • [26:58] Revenue
  • [27:20] The Wild Business Growth podcast is on YouTube! Subscribe @MaxBranstetter to watch full video interviews with Wild entrepreneurs like Sam
  • [27:58] Sign up for the Podcasting to the Max newsletter at MaxPodcasting.com/Newsletter and receive How to Edit Your Podcast in Audacity. It’s where podcasting meets entrepreneurship – and terrible puns
  • [28:00] Such an honor speaking at Podcast Movement ’23 in Denver! Sign up to grab the slides from my session at MaxPodcasting.com/PM23

• Inspiration & Creativity: Lessons from Sam’s Creative Parents
  • [28:42] What’s the story behind Sam’s mom’s paintings (Nancy Rosen)
  • [29:14] Grace and Frankie, Netflix, Lily Tomlin, Jane Fonda
  • [30;08] Shoutout, Dana!
  • [30:23] “The Art Show“
  • [30:34] Bazinga
  • [30:38] What commercials did Sam’s dad direct and produce
  • [31:11] Michael Jordan Chevy Blazer Commercial
  • [31:42] Did Sam’s dad get to meet Michael Jordan
  • [32:00] Cal Ripken, Jr., Bobby Cox, John Smoltz
  • [32:08] Atlanta Braves
  • [32:15] Atlanta Lottery (Georgia Lottery)
  • [32:51] What’s the most important lesson Sam learned from his parents about creativity and entrepreneurship
  • [34:21] Solon, OH
• Rapid-Fire Q&A
  • [35:12] Renga-Tei, Lula Cafe
  • [35:56] Furniture Creative Coworking
  • [36:54] How do you have a successful long-term relationship
  • [38:35] Chicago Architecture River Cruise Aboard Chicago’s First Lady, Chicago Riverwalk
  • [39:22] Groupon Electric Boat Chicago
  • [39:54] Shoutout, Spense!
  • [40:38] Breather, Industrious
  • [42:53] Connect with Sam at SammyRosen.com and Deskpass.com
  • [43:56] What are Sam’s Final Thoughts
  • [44:28] Branch Rickey Quote
  • [45:08] Follow the Wild Business Growth podcast and tell a friend about the podcast. And show love (or roast me) by leaving 5 stars on Apple Podcasts and/or Spotify
  • [45:19] The Wild Business Growth podcast is on YouTube! Subscribe @MaxBranstetter to watch full video interviews with Wild entrepreneurs like Sam
  • [45:34] Check out the Wild Business Growth podcast on Goodpods, where you can see what your favorite people are listening to
  • [45:35] Connect with me on LinkedIn, Instagram, Twitter (aka X), and Threads @MaxBranstetter and TikTok @WildBusinessGrowth
  • [45:38] Save time with your high-quality podcast. Email me at max@maxpodcasting.com to bring your podcast to life and use it as a business-building tool
  • [45:43] Sign up for the Podcasting to the Max newsletter at MaxPodcasting.com/Newsletter and receive How to Edit Your Podcast in Audacity. It’s where podcasting meets entrepreneurship – and terrible puns
  • Theme music: Freestyle Percussion Magik – “Jungle Tribe” – provided by Jamendo

What is the Wild Business Growth podcast?

Wild ideas. Wild growth. Every Wednesday morning a new entrepreneur joins the Wild Business Growth podcast to share the wildly creative and unusual ways they grew their business – and teaches you how to do it, too. Hear the minds behind WordPress, Stacy’s Pita Chips, Drybar, NFL RedZone, Big Mouth Billy Bass, the voice of Bart Simpson, and more Wild stories. Hosted by Max Branstetter (that’s me), Founder and Podcast Producer at MaxPodcasting.

How do you start a podcast?

Interested in starting a professional-sounding podcast for your brand, but don’t want to deal with the time commitment of all those behind-the-scenes details? I’ve got you covered. Email me at max@maxpodcasting.com to save time with your high-quality podcast and use it as a business-building tool.

Thanks for listening to Sam Rosen on the Wild Business Growth podcast. To hear more Wild stories like this one every Wednesday morning, follow the Wild Business Growth podcast and tell a friend about it. And become rock out on Deskpass with them. Until next time, Let your business Run Wild…and Bring on the Bongos!!