All Episodes

Displaying episodes 1 - 30 of 138 in total

How to win against well-funded competitors

 In this episode, we talk about how bootstrappers can win against companies that have raised massive amounts of money.Full topic list:We give an update on the compensa...

The one where we negotiate Tyler’s compensation

If you’ve been following along, you know that Tyler is about to temporarily join Rick’s startup to help build their new app. In this episode, we talk about the compens...

How we deal with security questionnaires

In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more.

Something new to announce

This week, we share some exciting news that impacts both of us.

Looking back at 2022 and forward to 2023

This is our yearly recap episode!

Big bets vs small bets

In this episode, we talk about prioritizing big revolutionary ideas vs small iterative improvements, and a whole lot more

How can founders use the new AI tech?

This week we talk about the recent boom in AI, and whether or not founders like us can take advantage of this new wave of innovation.

Professional hater

This week we talk about Twitter melting down, tech layoffs, and other generally unpleasant things that mostly haven’t effected us so far

An opportunity that comes along once per year

Most bootstrapped businesses are all about slow, steady, consistent growth. Rick’s business is different because he gets almost all his customers during one period eac...

What's priority #1?

In this episode, we talk about how easy it is to work on multiple things at once because it lets you avoid making tough prioritization decisions, and what we’re doing ...

The marketing tech stack

This episode, we talk about whether or not it makes sense to build home-made tools to help with marketing

How much to spend acquiring a customer

In this episode, we talk about CAC, customer acquisition costs, and how a startup can decide how much is too much to spend on acquisition.

The great re-org

In this episode, we talk about how we’re thinking about reallocating marketing and sales resources here at Less Annoying CRM.

Is SaaS getting harder?

Sometimes it feels like the tech industry is more of a zero-sum game than it used to be. We discuss that, and a lot more in this episode.

Single points of failure

Are single-points of failure sometimes ok? In this episode, we talk about how much redundancy a small company should have.

Should you hire a marketing agency?

In this episode, we talk about whether or not it makes sense for an early stage bootstrapped company to hire a marketing agency for help.

Healthy urgency

In this episode, we talk about healthy vs. unhealthy urgency, and whether it's realistic to hire a team of entirely high-urgency people

Prioritizing effectiveness over efficiency

In this episode, we've got a grab-bag of topics including when to worry about scaling, an argument against delegation, and a few shoutouts.

Charge Less

In this episode, we talk about how conventional wisdom around pricing is sometimes wrong.


In this episode, we discuss how the recent economic uncertainty might impact bootstrapped businesses.

How to be a mentor when you aren't knowledgeable about a topic

In this episode, we discuss how to connect employees with mentors when there's not already someone at the company with expertise.

Mission, Vision, and Values

This week, we talk about how to define the purpose and constraints of a business.

Tools don't solve problems

This episode, we've got a grab bag of different topics including a product-led growth discussion, what to do with a stagnent content site, and the role tools should pl...

Putting together a growth plan

This week, Rick helps Tyler think through a new growth plan for Less Annoying CRM

The importance of patience and impatience when hiring

This week, we talk about how both patience and impatience are important when hiring, how to learn new things, and more.

Funding your startup with a day job

This week, we talk about balancing a full-time job with running a startup, and a bunch of other stuff.

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...

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