Recent Podcast Episodes

#239: 7 is a Lot Closer to 10 than 1

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Today we chat with Charles and get an update on his new business, RelaNet. We talk about how he almost (but not quite) reached his 2017 goal, his struggles with taking on a sales role, learning from real customers, and dealing with rejection. Continue reading

#238: If You’re Free, Go to the Party

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Through his freelance design business, Joe has had clients for many years. Charles, on the other hand, is new to managing client relationships. So today we talk about how to handle those client relationships as we head into the holidays. Do you send a card? Do you send a gift? Do you attend the holiday party? What exactly should you do (or not do) during the holidays to nurture relationships with your clients? Continue reading

#237: Ian Landsman (part 2)

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Today we’re again joined by Ian Landsman, creator of HelpSpot and co-host of the Bootstrapped podcast. Ian has been building and running his self-funded helpdesk product HelpSpot for 13 years, and along the way he’s learned a lot of lessons about running a successful business online. Today we talk to Ian about the advice he gives to people building their first business, his new side project Thermostat.io, and his experiments with freemium in SaaS. Continue reading

#236: Ian Landsman (part 1)

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Today we’re joined by Ian Landsman, creator of HelpSpot and co-host of the Bootstrapped podcast. Ian has been building and running his self-funded helpdesk product HelpSpot for 13 years, and along the way he’s learned a lot of lessons about running a successful business online. Today we talk to Ian about how he got his start in entrepreneurship, how the business landscape has changed over his 13 years at HelpSpot, and how he manages to compete (and succeed!) in a market segment dominated by much larger, VC funded competitors. Continue reading

#235: Might Want to Pep That Up a Bit

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Today we start wrapping up the year by talking to Joe about how he’s done this year. We talk about his his goals for the year, what progress he made on them, and his plans for the future. Continue reading