Startup to Last

Rick Lindquist and Tyler King
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Oct 9, 2025 • 55min

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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Sep 25, 2025 • 55min

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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Sep 11, 2025 • 56min

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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Aug 14, 2025 • 54min

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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Jul 31, 2025 • 57min

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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Jul 17, 2025 • 53min

User communities

In this episode, we talk about trying to create a forum for Less Annoying CRM’s users.
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Jul 4, 2025 • 48min

SIP trunks

Rick and Tyler dive into techniques for smoking ribs, blending culinary skills with humor. They explore the perks and challenges of a four-day work week, arguing it boosts productivity. The conversation shifts to customer retention strategies, emphasizing the importance of renewals. Delving into VoIP systems, they discuss the advantages of SIP trunking and its integration into business communications. Finally, they consider new product opportunities and the strategic value of acquiring existing products to enhance their offerings.
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Jun 19, 2025 • 54min

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.TakeawaysTyler 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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Jun 5, 2025 • 55min

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.Chapters00:00 Parenting and Sleep Challenges03:29 Reading Habits and Fantasy Literature06:32 Business Growth and Revenue Updates09:21 Form Metrics and Marketing Strategies12:17 Internal Use Cases and New Features15:23 Exploring Industry-Specific CRM Opportunities21:22 Future of CRM and Industry Integration28:57 Navigating Software Integration Challenges32:34 The AI Dilemma: To Adopt or Not?37:13 AI Readiness: Preparing for the Future39:38 Revenue Metrics and AI Efficiency50:28 Exploring AI Opportunities in Customer Experience
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May 22, 2025 • 53min

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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