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What do you learn from a 20-year career building products for small businesses? Some things change, and some things stay the same, according to Brevi founder and CEO Randy Parker, our guest for Episode 1 of the Heard on the Street Podcast (listen above).

We have new technology in local, says Parker, including AI and an expanding marketing stack. This has provided tools to automate SMB marketing and save time, a founding principle for Brevi. But it’s also fueled the need to build more comprehensive one-stop-shop offers for SMBs, à la SMB OS.

“What we had 20 years ago is this fairly linear marketing challenge: I just need to get out in front of a customer to get them a message and bring them back,” says Parker. “Now we’ve gone from checkers to 3D chess: You’ve got to be doing social, you got to be mobile, and you’ve got to be very real time.”

Along with that evolution, there have been certain constants, such as the challenges of serving SMBs. And one longstanding truth has been that the best way to get an SMB’s attention is to get between them and their customer. That and the fact that they often defy logic when it comes to perceived ROI.

“I always say you can bring an [SMB] a machine that you put a $1.00 in, and it gives you $1.05 back, and they’ll say ‘leave me some literature,'” says Parker. “But if you are between something that they’ve got to do today with a customer, then you can get their attention.”

There’s also a combination of new and universal challenges involved in founding startups, he says. Those include scaling challenges, maintaining focus, and venture funding. Funding can be great, but it’s not the panacea it’s often made out to be in tech culture. It can bring dilution, limited exit options, and distraction.

We talk to Parker in Episode 1 about these and several other matters—everything from company culture to what it’s like to operate a business and live in Boston. We also find out that Parker is a “Buddhist who grew up in the hedonism capital of South Florida,” and who his role models are in business and beyond.

Check out the episode above, find out more here (subscription links coming soon), and stay tuned for episodes every two weeks.

Mike Boland is Street Fight’s lead analyst and author of the Road Map column. He covers AR & VR as chief analyst of ARtillry Intelligence, and SF President of the VR/AR Association. He has been an analyst in the local space since 2005, covering mobile, social and emerging tech.

Mike Boland has been a tech & media analyst for the past two decades, specifically covering mobile, local, and emerging technologies. He has written for Street Fight since 2011. More can be seen at