Rob Kenedi spent two days at Startupfest parked in the same spot under the same tent. All day he was there live-recording interviews with entrepreneurs, investors and others for his podcast, Entrepreneurs in Small Rooms Drinking Coffee.

The Toronto-based founder started the podcast in 2014 and has now recorded over 70 episodes, including intimate chats with Dragons’ Den Next Gen’s Nicole Verkindt, the founders of Wealthsimple, Upverter, Nymi and many more. At Startupfest, Kenedi recorded interviews with eventual $50,000 investment winner HelloMD, as well as startups like Parlay, Fans Unite, Gatsby, Zoom AI, Ubios, Tylio and Tunestars.

The impetus for creating the podcast was simple enough for Kenedi.

“I had served as a CEO or director for both funded and bootstrapped startups and especially when I was a CEO I was like, ‘Oh my god, it’s really hard.’ No one actually has the answer to your problem. Everyone has advice and it’s always conflicting,” said Kenedi.

At first Kenedi spoke about what he was feeling: just how hard it was to be a tried-and-tested entrepreneur and how we make the decisions we make. Above all he wanted to help other entrepreneurs.

“There’s a lot of buzz and uselessness on the Internet and the point of the show was to have honest conversations, or the kind of conversations that I was actually having both running and advising Startups,” Kenedi told MTLinTECH.

Over the years he’s published episodes that he thought would resonate well with listeners only to have them fall flat. Other episodes that he thought were awful attracted fanfare on social media.

“I had no idea what an interesting show would be,” said Kenedi.

One of those episodes was with Forewards, a startup that provided a customer referral network for Shopify store owners prior to Shopify’s IPO. Kenedi thought the episode was amazing, but he didn’t get the reaction he’d expected.

Eight months later, Kenedi interviewed Forewards again as the startup neared a collapse.

“That arch from excitement to failure was so interesting for me and [COO Jason Dea] was so observant about why he failed. He was like, ‘Here’s how Shopify works. Here’s how the average person selling isn’t sophisticated enough to understand they need a customer referral network, and so on.’ Catching those major inflection points in their life and having a really great reflection on it on an emotional level was just amazing. That really did it for me.”

Another favourite of Kenedi’s was when Nicole Verkindt, now a familiar face on CBC’s Dragons’ Den, came on the show. At the time the dragon admitted that she was still new to the investing world.

“My favourite moments have been when guests get to the core of it. They really admit that nobody actually knows how the future will turn out despite all the hype,” said Kenedi.

Kenedi wants to grow the show and he wants more listeners. Interestingly, the most popular time to listen to the show is on Saturday afternoons. Perhaps it’s just that time of the week where people can put everything down and just concentrate.

“There’s this solitary time for people when they listen to audio. With audio, the human brain can only listen to one thing at one time, so podcasting is a very intimate experience.”