All Episodes

Displaying episodes 31 - 60 of 142 in total

Giving early hires skin in the game

This week, we talk about how Rick can structure a compensation plan with his first hire to make them feel like a true partner. Most startups give equity, but that isn’...

Rebirth / Welcoming 2022

The rumors were true. Startup to Last is back, and we're starting out with a recap of 2021 and a look forward to 2022.

The final episode

We've got some bittersweet news. Rick has accepted a new job which isn't really a fit for the topics we discuss on this podcast. Because of that, we've decided that th...

Sustainability starts with planning

This week, many of our topics have a common theme: How do you put a plan together to run a sustainable company? I mean, this podcast is called "Startup to last" so I g...

What to cut and what to keep

This week, we talk about simplifying a business. How do you know what complexity is important to the business, and what can get cut?

Home runs vs. consistency

This week, we discuss the difference between things that require big one-time achievements vs things that require lots of gradual, consistent improvement. Let's go.

Throwing things at the wall to see what sticks

This week, we discuss whether or not Rick can cut out some of the complexity from his business now that he knows what's working and what's not.

The thing about utopias is that they're not real

This week, we discuss how building a business is like building your own personal utopia. Or maybe that's a fantasy.

Sharing profit with employees

This week we get a bit philosophical. If a business has extra profits, how can they be fairly shared with employees and other stakeholders?

When platform risk goes wrong

One of Rick's API vendors shut down his account without warning, which throws a wrench in his productized service. This week, we discuss how he should respond.

When churn and word of mouth cancel each other out

This week, we talking about what happens when churn and word of mouth cancel each other out, what we're doing to focus on the right types of work, and more.

What we've learned about podcasting after 100 episodes

We're going to be a bit self-indulgent this week. This is our 100th episode, and so in this episode, we reflect on the experience and share what we've learned.

Content marketing: Putting all our eggs in one basket

This week, we talk about an idea we have at Less Annoying CRM to do content marketing all focused around one really good piece of content rather than our normal strate...

What does a $100k/year support person look like?

This week, we discuss what the role of a highly skilled, highly compensated support person would be. Let's go.

Can a course business succeed even if no one finishes them?

This week, we dive into one of the big drawbacks of online courses: That not very many people actually complete them.

Making your first hire

This week, we answer a few listener questions about how to make your first hire.

When customer expectations aren't met

This week, we discuss a situation Rick is dealing with where a customer is disappointed and feels that their expectations weren't met.

The Theory of Constraints

This week, we discuss the theory of constraints: A mental model for deciding what to focus on as an entrepreneur.

The importance of internal communication

This week, we give a bunch of updates on what we're working on, and end with a long, rambly, inconclusive discussion about the recent Basecamp drama.

Empowering employees to be leaders

This week, we talk about some new announcements Tyler just made at Less Annoying CRM, including a new leadership team.

Time management

This week, we talk about some time management hacks Rick is trying now that he has a baby to take care of.

$2k MRR

This week, we talk about Rick's latest milestone, how to hire a developer, and more.

Jamming with Dru Riley from

This is a special episode where Dru and Tyler "jam" on one of the topics for Dru's reports.

Deep dive into an execution retreat

Because Rick is taking some time off for parental leave, we recorded a special episode this week. Rick is about to do a week-long retreat to try to finish a major proj...


This week, we talk about how to identify burnout, and what to do about it.

Enterprise sales is just project management

This week, we talk about what the new stimulus bill will mean for entrepreneurs, and we discuss some learnings from an ongoing enterprise sales project.

What does's move mean for startup to last companies?

Earlier this week, Indie.VC, one of the main sources of financing for companies like the ones we run on this show, announced they're shutting down due to challenges fi...

Hardcore week building a content site

This week, we talk about the strategy around Tyler's new content site

Content marketing when you're not a domain expert

This week, we talk about a the difficulties of content marketing when you're not a domain expert, healthy vs. unhealthy deadlines, and more.

Separating decision making from executing

This week we talk about the benefit of making decisions separately from executing on those decisions, whether or not it's risky to share internal metrics publicly, and...

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