
Startup to Last
Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.
Latest episodes

Jun 6, 2024 • 51min
Step on the gas, or pull back?
In this episode, we talk about a decision Rick needs to make with LegUp Health. Should he treat it like a high-growth startup, or a lifestyle business?

May 16, 2024 • 52min
We ain't talking about zero to one
The hosts dive into the nuances of moving from early-stage startups to sustainable growth, questioning the universal application of traditional advice. They share quirky anecdotes, like dressing up as 'The Lord of the Rings' characters at an internship. The discussion shifts to the complexities of outbound sales, emphasizing quality over quantity in outreach. They also explore transitioning customers to a new product version, highlighting the importance of communication and user engagement during launches. The blend of strategy and personal stories keeps it relatable and engaging.

May 9, 2024 • 49min
Forms forms forms
In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the business

Apr 25, 2024 • 41min
Leveling up the team
In this episode, we discuss using consultants to level up your team.

Apr 11, 2024 • 55min
The first step of a flywheel
In this episode, Rick explains how he’s getting more hands on with marketing.

Mar 28, 2024 • 52min
Sometimes you need to touch the hot stove
In this episode, we discuss how some lessons can't be taught, they have to be learned through experience. What does that mean for mentoring less experienced employees?

Feb 29, 2024 • 49min
When to outsource
In this episode, we talk about when it makes sense to outsource work to contractors and agencies, vs when it makes sense to do something in-house.

Feb 15, 2024 • 40min
Talk to sales
In this episode, we talk about Less Annoying CRM’s latest sales experiment.

Feb 1, 2024 • 46min
Learnings from a few days of snowboarding
In this episode, we talk about takeaways from big snow tiny conf, and more.

Jan 18, 2024 • 50min
Profit first
In this episode, we discuss how Rick is using the “profit first” mindset to manage company finances.