Best Rick Lindquist Podcasts (2026)

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2025 Recap 1:57:30

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6d ago1:57:30

1:57:30

This is our annual recap episode. We talk about how things went in 2025 and what we’re hoping to see in 2026. Personal goals for 2026 Rick Getting back to basics Going from reactive to proactive (and surviving to thriving) Shifting from a strategy of playing it safe and reducing risk to taking smart risk and being ok looking a little foolish Tyler …

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Can Rick’s optimism defeat Tyler’s pessimism? 49:14

1M ago49:14

49:14

In this episode, we once again talk about AI, and oh boy do we get off topic. Here's the AI tool Rick mentioned for recording your screen (we'll talk about that in a future episode) Here's the AI report Rick mentionedBy Rick Lindquist and Tyler King

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Open Enrollment Woes 44:50

2M ago44:50

44:50

In this episode, Tyler and Rick discuss the challenges faced by Leg Up Health during open enrollment, including issues with email communication and the impact of AI on consumer behavior. They explore the current health insurance landscape, the importance of product strategy and customer experience, and the role of content in engaging customers. The…

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Does OG inbound marketing still work? 49:59

2M ago49:59

49:59

In this episode, we talk about whether Rick’s expertise with traditional inbound marketing will work for LegUp Health.By Rick Lindquist and Tyler King

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ICP ICP ICP 54:51

3M ago54:51

54:51

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.By Rick Lindquist and Tyler King

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What to do while you’re waiting for results 54:46

3M ago54:46

54:46

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.By Rick Lindquist and Tyler King

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Website overhaul 56:29

4M ago56:29

56:29

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

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We're profitable, now what? 53:36

5M ago53:36

53:36

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

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Tiers, add-ons or standalone products? 57:06

5M ago57:06

57:06

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.By Rick Lindquist and Tyler King

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User communities 53:13

6M ago53:13

53:13

In this episode, we talk about trying to create a forum for Less Annoying CRM’s users.By Rick Lindquist and Tyler King

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SIP trunks 48:04

6M ago48:04

48:04

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 technic…

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Add-on product 54:28

7M ago54:28

54:28

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 eff…

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Will these guys please stop talking about AI 54:47

7M ago54:47

54:47

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 effi…

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Acquisition vs Expansion 52:48

8M ago52:48

52:48

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 custom…

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Vibe coding 57:25

9M ago57:25

57:25

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 developme…

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What do all these customers have in common? 55:42

9M ago55:42

55:42

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 maintaini…

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Dipping a toe in the AI waters 54:39

10M ago54:39

54:39

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 use…

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Consultative sales 51:45

10M ago51:45

51:45

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 need…

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Lowering the bar 47:41

11M ago47:41

47:41

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

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Line go up 44:40

12M ago44:40

44:40

In this episode, we talk about some metrics that are headed in the right direction. Let’s goBy Rick Lindquist and Tyler King

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Rating growth channels 48:29

1y ago48:29

48:29

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

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2024 Recap 1:11:26

1y ago1:11:26

1:11:26

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 st…

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Different types of hiring 51:51

1y ago51:51

51:51

In this episode, we discuss how there are multiple different approaches to take when a startup needs to grow the team.By Rick Lindquist and Tyler King

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Bluesky is back 47:09

1y ago47:09

47:09

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

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How we know if a feature is ambitious enough 46:49

1y ago46:49

46:49

Less Annoying CRM is working on some big features, and in this episode, we discuss what we’re learning as a result.By Rick Lindquist and Tyler King

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Everybody’s marketing 53:42

1y ago53:42

53:42

We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying.By Rick Lindquist and Tyler King

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How’s 2024 going 55:24

1+ y ago55:24

55:24

In this episode, we review our yearly goals, talk about some new AI tools we’re trying out, and more.By Rick Lindquist and Tyler King

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How AI might impact customer service 50:25

1+ y ago50:25

50:25

In this episode, we talk about how we’re thinking about customer service in a world of AI*, and we do a deep dive into a customer interview Rick did recently. *Clickbait warning: We don't actually spend much time on this topic, I just wanted a catchy title for the episode. Did it work? Did you listen because of my misleading title? Let me know in t…

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The internet isn’t fun anymore 49:01

1+ y ago49:01

49:01

In this episode, we talk about the value of a podcast community, and generally how we’re trying to protect ourselves from the internet.By Rick Lindquist and Tyler King

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How to raise revenue by 20% in one day 45:57

1+ y ago45:57

45:57

In this episode, we talk about about the impact a recent price change is having on Less Annoying CRM’s finances.By Rick Lindquist and Tyler King

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Small bets vs going deep 43:23

1+ y ago43:23

43:23

The internet loves to talk about whether to focus on a single business or build a portfolio of small bets. I’m sure you’re sick of hearing about it. But in this episode, we have a twist on that topic. For an established business thinking about launching complimentary products, is it better to build one great one, or a series of only ok ones.…

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Pick one thing and max it out 46:59

1+ y ago46:59

46:59

In this episode, we talk about how the job of an entrepreneur isn’t to decide which ideas are good and which are bad. It’s to pick the single best idea out of a sea of good ideas.By Rick Lindquist and Tyler King

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Step on the gas, or pull back? 51:15

1+ y ago51:15

51:15

In this episode, we talk about a decision Rick needs to make with LegUp Health. Should he treat it like a high-growth startup, or a lifestyle business?By Rick Lindquist and Tyler King

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We ain't talking about zero to one 52:29

1+ y ago52:29

52:29

In this episode, we talk about how a lot of startup advice is focused on businesses going from zero to one, and how we have to be careful not to assume that all applies to us.By Rick Lindquist and Tyler King

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Forms forms forms 49:01

1+ y ago49:01

49:01

In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the businessBy Rick Lindquist and Tyler King

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Leveling up the team 40:48

1+ y ago40:48

40:48

In this episode, we discuss using consultants to level up your team.By Rick Lindquist and Tyler King

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The first step of a flywheel 54:38

1+ y ago54:38

54:38

In this episode, Rick explains how he’s getting more hands on with marketing.By Rick Lindquist and Tyler King

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Sometimes you need to touch the hot stove 52:26

2y ago52:26

52:26

In this episode, we discuss how some lessons can't be taught, they have to be learned through experience. What does that mean for mentoring less experienced employees?By Rick Lindquist and Tyler King

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When to outsource 49:08

2y ago49:08

49:08

In this episode, we talk about when it makes sense to outsource work to contractors and agencies, vs when it makes sense to do something in-house.By Rick Lindquist and Tyler King

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Talk to sales 39:33

2y ago39:33

39:33

In this episode, we talk about Less Annoying CRM’s latest sales experiment.By Rick Lindquist and Tyler King

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Learnings from a few days of snowboarding 46:21

2y ago46:21

46:21

In this episode, we talk about takeaways from big snow tiny conf, and more.By Rick Lindquist and Tyler King

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Profit first 50:05

2y ago50:05

50:05

In this episode, we discuss how Rick is using the “profit first” mindset to manage company finances.By Rick Lindquist and Tyler King

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Looking back at 2023 and forward to 2024 1:28:15

2y ago1:28:15

1:28:15

This is our yearly recap episode! Personal updates from 2023 Tyler Goals from last year 🆗 Take more vacation and make up with with extra work off-hours work 🆗 Renovate the house Other updates Found a band I like: Caligula's Horse First time as an adult I feel good about my exercise routine Rick Goals from last year ❌ Get weight below 200lbs ❌ Write…

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DEI isn't dead 50:01

2y ago50:01

50:01

In this episode, we talk about Rick's open enrollment experience, and what LACRM is doing related to DEI (diversity, equity, and inclusion)By Rick Lindquist and Tyler King

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Growth is hard 57:48

2y ago57:48

57:48

In this episode, Rick tries to explain to me that there are people who know how to grow businesses, and I stubbornly insist otherwise.By Rick Lindquist and Tyler King

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Inflection point 51:46

2y ago51:46

51:46

In this episode, we discuss what feels like an inflection point in Rick's business. Full topic list: LegUp Health has a new website. Rick thinks he's feeling an inflection point. We daydream about the future of LegUp Health a bit. Things are calm at LACRM, and the employees are all increasingly experienced. Tyler is coding again. There's a new buzz…

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Reducing Friction 34:16

2y ago34:16

34:16

This week, we discuss how LegUp Health reduced a major point of friction when selling to employers. Here's the full topic list: Rick is finally in his new house, and a major stress has been removed. Rick gives updates on LegUp Health, including a major unlock to getting employers onboard. Rick talks about progress towards hitting annual sales goals…

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Build it and they will come 53:27

2y ago53:27

53:27

In this episode, we discuss whether or not building features customers ask for is a valid path toward growth. Here are all the topics: LACRM has started migrating to Paddle. LegUp Benefits has its first official customer! We discuss how LACRM's free trial pipeline isn't as correlated with paying user growth as you'd expect. We dive deep into the hi…

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The pricing change I didn’t want to make 42:20

2+ y ago42:20

42:20

This week, we talk about a pricing change we recently announced at Less Annoying CRM. We dive into the history behind the decision, how it was communicated, what it means for the finances of the business, and more.By Rick Lindquist and Tyler King

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Reorg 42:37

2+ y ago42:37

42:37

In this episode, we discuss a hodgepodge of things including a company reorg, growth tactics, and more. Here are all the topics: Rick updates us on LegUp Health's progress. He talks about working on the sales pitch, building momentum, staying focused, and more. Tyler is merging two teams at LACRM. We discuss what the impact of that change might be.…