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 Trends.vc
This is a special episode where Dru and Tyler "jam" on one of the topics for Dru's trends.vc 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...
Burnout
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 Indie.vc'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...