Advice From SaaS Founders: The Playlist

The Long, Slow, SaaS Ramp Of Death: Gail Goodman

One of the most-watched BoS talks, and with good reason. Here Gail Goodman describes the difficulty of growing Constant Contact, and what they did to overcome the roadblock.

Healthy, Wealthy, & Wise: Jason Cohen

Jason Cohen is a hugely successful entrepreneur – he is the founder of Smart Bear Software and WP Engine.. In this, his 4th talk at Business of Software Conference, he raises the issue of Founder Health. Are you the Hacker News ‘Founder in Pain’? Or maybe you struggle making the big, emotional decisions that necessarily come with running a business? Jason has words of comfort and challenge for you.

Keeping The Fun In Your Business Life: Natalie Nagele

Why are you running a business? That’s the question Natalie poses in this inspiring talk from BoS USA 2017. Natalie talks about the importance of putting your team first, and how to make sure you’re pursuing your own goals, and not just feeding ‘The Beast’.

What I’ve Learned In 10 Years Of Balsamiq: Peldi Guilizzoni

In this talk from BoS USA 2018 Peldi shared an honest update about his worries in Balsamiq’s milestone 10th year. On realizing he’s still too integral to the business, Peldi started the ‘Winter 2018 Injected Turbulence Project’ – delegated product design and engineering management, deleted Slack and Twitter from his phone, and stopped watching their internal wiki.

Facing Fears (Growing Bigger By Growing Bolder): Dharmesh Shah

In this talk from BoS USA 2019, Hubspot founder Dharmesh Shah talked about facing his fears about the future of Hubspot.

Online workshops

New to AI in your business?

AI in Your Business: Where to Start

Set up your AI company OS. Two sessions, cohort of 12.

“I’ve been talking to it loads about positioning, sales framing, North Star metrics. I came up with a succinct statement that I really like.”

Marv Rance, InTouch

Register now Want to do it with just you? One-on-one option ›

Already set up your OS?

Building Your AI Company
Operating System

Not sure what to do next. Four weeks, cohort of 12, with Tim Barker and Mark Littlewood.

“I think about the business differently than I used to. I would never have come to that conclusion without this process.”

Stephen, cohort participant

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Conference

In-person BoS Conference 2026

Date TBA ⌄

📅 Date TBA 📍 In-person

Two days with software founders and leaders who have actually built profitable businesses. No panels, no keynotes designed to impress. Talks that earned their place because the idea was worth the room’s time.

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