Startup to Last

Apr 10 2025 181 ep. 57 mins 147
Startup to Last Podcast artwork

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.

  Business
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What do all these customers have in common?

Apr 10 2025 55 mins  
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

Dipping a toe in the AI waters

Mar 27 2025 54 mins  
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 pa

Consultative sales

Mar 13 2025 51 mins  
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

Lowering the bar

Feb 20 2025 47 mins  
In this episode, we talk about how Rick has given himself some breathing room, and how that’s impacted his outlook on the business.

Line go up

Jan 16 2025 44 mins  
In this episode, we talk about some metrics that are headed in the right direction. Let’s go

Rating growth channels

Jan 02 2025 48 mins  
In this episode, we try to prioritize some of the different growth channels Rick is considering for 2025.

2024 Recap

Dec 19 2024 71 mins  
In this episode, we recap 2024 and set goals for 2025:Personal goals for 2025:Rick: Primary theme: Buy back timeTake 1 personal day every 1-2 monthsGet 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 timesTylerBaby stuffRemain flexible and do whatever needs

Different types of hiring

Dec 05 2024 51 mins  
In this episode, we discuss how there are multiple different approaches to take when a startup needs to grow the team.

Bluesky is back

Nov 21 2024 47 mins  
In this episode, we discuss Bluesky as the new Twitter, how Rick’s busiest time of year is surprisingly calm, and more.

How we know if a feature is ambitious enough

Nov 07 2024 46 mins  
Less Annoying CRM is working on some big features, and in this episode, we discuss what we’re learning as a result.