Startup to Last

In this episode, Rick helps Tyler think through how to roll out a major product redesign for his 20,000 users. Tyler has a plan, but he’s concerned about losing customers through the transition. His biggest roadblock is figuring out how to roll this out without causing his customers to get angry and leave. After going back and forth, the following framework emerged for communicating major product...

In this episode, Tyler helps Rick evaluate how to build a new software application from scratch. Since Rick is a nontechnical founder, his biggest roadblock is figuring out how to build the application without raising money. After going back and forth, the following framework emerged for nontechnical founders trying to hire a first employee: What is the idea (i.e. problem and solution)? What type...

What’s an employee handbook? Tyler: The topic this week is employee handbooks. This has been on my mind because we redid our whole employee handbook this last spring leading up to hiring some new people. So I rewrote it and put a lot of thought into it, but I wanted to talk through it with you. I'd like to cover things like what should actually go into it. And one thing that I hadn't thought of pr...

Tyler: In this episode, we're gonna talk about the pros and cons of remote work, such as when does it make sense for a company to have employees altogether in an office versus fully remote or something in between. Rick: I personally get this all of the time. I've heard of four core models that . One is “single site” which means everyone works in the same office environment. Second, is “multi-site”...

The role of a small business or startup CEO Tyler: In this episode, we're going to talk about what the role of a CEO should be at a small business or a startup. I always hesitate to call myself a CEO, depending on who I'm talking to because it seems a little pretentious. I run a 17-person company and some days, I don't do any CEO stuff: I just write code or design something. And some days I'm in m...

Tyler: In this episode, we're going to talk about impostor syndrome. Do you want to kind of explain what you had in mind here? Rick: Yeah. So you know this. I left PeopleKeep after 11 years. For most of the time, I was the leader of the company under various titles, most recently CEO. I left in October. So it's been about nine months now. Rick: One of the big reflections I had was sometimes how I...

In this episode, we discussed salary transparency. After some back and forth, we concluded that a company’s salary transparency policy should be based on its personnel strategy. In other words, how you handle salary transparency, whether it's no transparency, partial transparency or full transparency, entirely depends on the people you have and more importantly the people you want to attract. Befo...