Rephonic
Artwork for Startup to Last
Less Annoying CRM
Legup Health
Entrepreneurship
Health Insurance
Saas
Open Enrollment
Project Management
Customer Service
Bluesky
Product Development
Customer Engagement
Twitter
Leg Up Health
Sales Strategies
Growth Opportunities
Software Development
Business Strategy
Customer Retention
Ideal Customer Profile
Affordable Care Act

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.

PublishesTwice monthlyEpisodes206Founded7 years ago
Number of ListenersCategories
MarketingBusinessEntrepreneurship

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Artwork for Startup to Last

Latest Episodes

In this episode, we talk about using AI to answer questions based on content in a knowledge base. It’s easy to get a proof of concept working, but how do you continuously improve it from there? Is that even realistic with current technology? All that... more

In this episode, we dive into one of the most exciting topics imaginable: HIPAA compliance

In this episode, we dive deep into Less Annoying CRM’s new marketing strategy.

In this episode, we talk about how one of the new business challenges is to figure out what skills are uniquely human, and leaning into those things as your differentiator.

Key Facts

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Number of Listeners
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Hosts

Tyler
Host of the show; co-founder of Less Annoying CRM; occasional contributor with a focus on marketing, product strategy, and bootstrapped software.
Rick
Host of the show; co-founder/CEO of LegUp Health; focuses on health-tech, software product strategy, and startup execution.

Reviews

5.0 out of 5 stars from 42 ratings
  • Great Show!

    If you want to feel like a fly on the wall, listening to a conversation between two entrepreneurs, then this show is for you. I appreciate Tyler and Rick sharing all the different aspects of their business with us on air. And the advice they give is top notch!

    Apple Podcasts
    5
    PaigeBPodcasting
    United States3 years ago
  • Transparent and helpful

    I like how Tyler and Rick are transparency about problems they face. Plus, they encourage each other. It's a good energy.

    Apple Podcasts
    5
    Jkjjjkkkk
    United States5 years ago
  • Solid podcast by 2 genuine guys

    Great podcast by two genuine guys sharing their thoughts, challenges, and ideas openly, without hype. Highly recommend for any bootstrapper or small business entrepreneur.

    Apple Podcasts
    5
    mhamblin63
    United States5 years ago
  • Nice relaxed style

    Only began dipping into the back catalogue recently but have enjoyed each episode so far.

    Plenty of general business advice as well as specific to start-ups / side hustles, so useful for employees as well as entrepreneurs.

    Apple Podcasts
    5
    Reevio
    United Kingdom5 years ago
  • I like it

    I’ve listened to about 6 or 7 eps and just picking topics I like. The chat these guys go through is pretty interesting when they’re working through a problem. Looking into being a start up myself it’s so refreshing to listen to people who have started businesses that don’t have it all sorted out up front and just feeling their way through. I like it.

    Apple Podcasts
    5
    Kg.dub
    Australia5 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

They appreciate the helpful, actionable insights derived from real-world experiments and dual-CEO perspectives.
Listeners value the practical, no-fluff approach and transparency in sharing both wins and challenges.
The conversational format feels relatable and non-scripted, which many find refreshing and inviting.

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Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Startup to Last

What is Startup to Last about and what kind of topics does it cover?

The show centers on two bootstrapped SaaS founders who explore how to build software businesses that endure. Episodes swing between practical product and GTM tactics (ICP definition, pricing experiments, ARPU expansion ideas) and broader business strategy (marketing attribution, AI tooling, human-centered execution, and industry shifts like health-insurance tech). A recurring strength is their transparent, no-nonsense dialogue—balancing optimism with realism, sharing concrete experiments, failures, and lessons in real time. Noteworthy is the mix of hands-on, coder-to-CEO insights with strategic pivots, often anchored by deep dives into go-to-market, product iteration, and sustainable growth strategies that appeal to founders, small teams, a... more

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Which podcasts are similar to Startup to Last?

These podcasts share a similar audience with Startup to Last:

1. The Panel
2. Startups For the Rest of Us
3. Permission Not Required
4. Mostly Technical
5. Still Early

How many episodes of Startup to Last are there?

Startup to Last launched 7 years ago and published 206 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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