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Startup to Last
Rick Lindquist and Tyler King
192 episodes
20 hours ago
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.
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Entrepreneurship
Business,
Marketing
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All content for Startup to Last is the property of Rick Lindquist and Tyler King and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Show more...
Entrepreneurship
Business,
Marketing
Episodes (20/192)
Startup to Last
ICP ICP ICP

We spend the entire episode diving into how we can better define Less Annoying CRM’s ideal customer profile, and what that would mean for the product and marketing.

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3 weeks ago
54 minutes

Startup to Last
What to do while you’re waiting for results

In this episode, we talk about what the Less Annoying team should be working on while waiting to see if the last bet actually pays off.

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1 month ago
54 minutes

Startup to Last
Website overhaul

In this episode, we talk about how Rick can overhaul the LegUp Health website to fit their new positioning.

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1 month ago
56 minutes

Startup to Last
We're profitable, now what?

In this episode, Rick shares how he approached thinking about what to do with his first meaningful profit.

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2 months ago
53 minutes

Startup to Last
Tiers, add-ons or standalone products?

In this episode, we dive into where things stand with Less Annoying CRM’s potential new product.

Here's the blog post about First Team Principles Rick mentioned.

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3 months ago
57 minutes

Startup to Last
User communities

In this episode, we talk about trying to create a forum for Less Annoying CRM’s users.

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3 months ago
53 minutes

Startup to Last
SIP trunks

In this conversation, Rick and Tyler explore various topics ranging from smoking techniques and the evolution of grilling methods to the challenges and benefits of a four-day work week. They discuss business growth strategies, particularly focusing on customer retention and the importance of securing renewals. The conversation shifts to the technical aspects of VoIP systems, including SIP trunking, and the implications of AI on search optimization. Finally, they delve into potential new product opportunities and the strategic considerations of acquiring existing products to enhance their offerings.

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4 months ago
48 minutes

Startup to Last
Add-on product

In this conversation, Rick and Tyler discuss various topics ranging from their beverage preferences to the latest trends in podcasts, business growth, and the integration of AI in their operations. They explore the significance of setting revenue goals, the role of AI agents in customer outreach, and the development of internal tools to enhance efficiency. Additionally, they delve into potential new product opportunities, customer feedback, and pricing strategies for future offerings, concluding with reflections on their business direction.

Takeaways

  • Tyler prefers soda over coffee for his morning routine.
  • Rick has re-engaged with podcasts, discovering new content.
  • Leg Up Health achieved a record revenue month, nearing their goal.
  • Setting realistic revenue goals can provide relief and stability.
  • AI integration is becoming crucial for business operations.
  • Internal tools can significantly improve team efficiency.
  • Customer feedback is essential for product development.
  • Pricing strategies need careful consideration for new offerings.
  • Exploring new product opportunities can enhance revenue per user.
  • Authenticity in customer outreach is vital for engagement.


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4 months ago
54 minutes

Startup to Last
Will these guys please stop talking about AI

In this conversation, Tyler and Rick discuss various topics ranging from personal experiences with parenting and reading habits to business growth strategies and the integration of AI in their respective companies. They explore the challenges of managing growth, the importance of understanding customer needs, and the potential of AI to enhance efficiency and customer experience. The discussion also touches on the significance of vertical integration and the future of AI in business, emphasizing the need for companies to be prepared for technological advancements while maintaining a focus on customer service.

Chapters
00:00 Parenting and Sleep Challenges
03:29 Reading Habits and Fantasy Literature
06:32 Business Growth and Revenue Updates
09:21 Form Metrics and Marketing Strategies
12:17 Internal Use Cases and New Features
15:23 Exploring Industry-Specific CRM Opportunities
21:22 Future of CRM and Industry Integration
28:57 Navigating Software Integration Challenges
32:34 The AI Dilemma: To Adopt or Not?
37:13 AI Readiness: Preparing for the Future
39:38 Revenue Metrics and AI Efficiency
50:28 Exploring AI Opportunities in Customer Experience

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5 months ago
54 minutes

Startup to Last
Acquisition vs Expansion

In this conversation, Tyler and Rick discuss the challenges and adjustments of parenthood, particularly Tyler's experience as a new father. They explore the balance between work and family life, the dynamics of business growth, and the implications of freemium models in their respective companies. The discussion delves into the importance of customer retention versus acquisition, the value of free users, and the efficiency required in service-heavy business models. Throughout the conversation, they share insights on navigating these complexities while maintaining a focus on long-term success. In this conversation, Tyler King and Rick discuss various topics including the implications of free trials on conversion rates, the integration of AI in coding practices with tools like Cursor, and the evolving landscape of client retention and revenue trends. They also delve into the recent changes in Apple's App Store pricing policies and their impact on developers, as well as the importance of understanding customer segmentation in business strategy.

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5 months ago
52 minutes

Startup to Last
Vibe coding

In this conversation, Tyler King shares his experiences as a new father while balancing work responsibilities. The discussion transitions into Tyler's recent work on LegUp Health, focusing on the challenges and opportunities in building a health insurance platform. They explore the concept of 'vibe coding' and how AI is reshaping software development and content creation. The conversation concludes with a brainstorming session on packaging benefits for LegUp Health, emphasizing the importance of clear communication and demonstrating value to potential clients.

Takeaways

Fatherhood brings unexpected challenges and joys.
Work-life balance is crucial for new parents.
Fundraising milestones can be a time for reflection.
Vibe coding allows for rapid development with AI assistance.
AI can enhance productivity but may lead to fragility in code.
Clear communication is key in demonstrating value to clients.
Packaging benefits effectively can unlock new opportunities.
Understanding the market is essential for product success.
AI tools can streamline content creation processes.
The future of work may require new skills and adaptability.

Chapters

00:00 The Journey of Fatherhood
03:16 Navigating Work-Life Balance
06:21 Milestones in Professional Growth
09:09 The Dynamics of Startups
12:11 Innovations in Health Tech
15:20 Vibe Coding and AI in Development
18:19 The Future of Software Development
21:11 Content Creation with AI
25:43 Navigating the AI Landscape
32:56 The Future of Learning in an AI World
37:26 Innovating Benefit Programs
49:06 Packaging Value in Health Benefits

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6 months ago
57 minutes

Startup to Last
What do all these customers have in common?

In this conversation, Tyler and Rick discuss various aspects of long-term product strategy at Less Annoying CRM, including personal updates, business growth, customer retention challenges, economic concerns, product development, and the importance of identifying ideal customer personas. They explore the balance between adding features and maintaining simplicity, as well as the need to adapt to changing market conditions.

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6 months ago
55 minutes

Startup to Last
Dipping a toe in the AI waters

In this conversation, Tyler and Rick discuss the challenges and triumphs of managing projects within SaaS companies, particularly focusing on the effective use of AI, sales pipeline dynamics, and the balance between calm and chaos in business operations. They explore the importance of setting realistic goals, the role of automation in enhancing user experience, and the impact of parental leave on work dynamics. The discussion emphasizes the need for focused opportunities in sales and the potential of AI to streamline processes and improve customer service.

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7 months ago
54 minutes

Startup to Last
Consultative sales

In this episode, Tyler and Rick discuss various sales best practices, focusing on the importance of maintaining a clean sales pipeline, optimizing CRM usage, and enhancing marketing strategies. They delve into the challenges of customer service and the need for a consultative approach to selling, emphasizing the value of understanding customer needs and providing tailored solutions. The conversation also touches on the updates to their form builder and the strategies being implemented to increase user engagement and satisfaction.

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7 months ago
51 minutes

Startup to Last
Lowering the bar

In this episode, we talk about how Rick has given himself some breathing room, and how that’s impacted his outlook on the business. 

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8 months ago
47 minutes

Startup to Last
Line go up

In this episode, we talk about some metrics that are headed in the right direction. Let’s go

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9 months ago
44 minutes

Startup to Last
Rating growth channels

In this episode, we try to prioritize some of the different growth channels Rick is considering for 2025.

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10 months ago
48 minutes

Startup to Last
2024 Recap

In this episode, we recap 2024 and set goals for 2025:

Personal goals for 2025:

  • Rick: Primary theme: Buy back time
    • Take 1 personal day every 1-2 months
    • Get time back for things I love (skiing, basketball, be present on vacations, reading/writing, local networking)
    • Have a familiy vacation on the calendar to look forward to at all times
  • Tyler
    • Baby stuff
      • Remain flexible and do whatever needs to be done
      • Create space for Shelly to have a life outside of just parenting
      • Take advantage of the calm life I've built
    • Don't hold myself to all my pre-baby health goals, but don't totally give them up either

Professional goals for 2025:

  • Rick
    • Legup Health: I don't know yet, but most likely...
      • 2x revenue (maybe less)
      • Make sure JD's role is sustainable
      • Make sure the business is properly financed
    • Windfall: Scale myself. Level up, and make sure the team levels up with me
  • Tyler
    • Don't worry about growth. Focus on input, not output.
    • Product
      • Tie off the big 2024 projects
      • Definitely ship kanban and a mobile app
      • Stretch goal: Ship one other big thing (sending email, automations, or reports)
    • Reduce the set of things I'm responsible for so I can focus on the things I'm best at
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10 months ago
1 hour 11 minutes

Startup to Last
Different types of hiring

In this episode, we discuss how there are multiple different approaches to take when a startup needs to grow the team.

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11 months ago
51 minutes

Startup to Last
Bluesky is back

In this episode, we discuss Bluesky as the new Twitter, how Rick’s busiest time of year is surprisingly calm, and more.

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11 months ago
47 minutes

Startup to Last
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.