Startup to Last

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.

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.TakeawaysFatherhood 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.Chapters00:00 The Journey of Fatherhood03:16 Navigating Work-Life Balance06:21 Milestones in Professional Growth09:09 The Dynamics of Startups12:11 Innovations in Health Tech15:20 Vibe Coding and AI in Development18:19 The Future of Software Development21:11 Content Creation with AI25:43 Navigating the AI Landscape32:56 The Future of Learning in an AI World37:26 Innovating Benefit Programs49:06 Packaging Value in Health Benefits

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.

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.

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.

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

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

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

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 to be doneCreate space for Shelly to have a life outside of just parentingTake advantage of the calm life I've builtDon't hold myself to all my pre-baby health goals, but don't totally give them up eitherProfessional goals for 2025:RickLegup Health: I don't know yet, but most likely...2x revenue (maybe less)Make sure JD's role is sustainableMake sure the business is properly financedWindfall: Scale myself. Level up, and make sure the team levels up with meTylerDon't worry about growth. Focus on input, not output.ProductTie off the big 2024 projectsDefinitely ship kanban and a mobile appStretch 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

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

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

Less Annoying CRM is working on some big features, and in this episode, we discuss what we're learning as a result.

We're both in marketing mode right now. In this episode, we dive into the specifics of what we're trying.

In this episode, we review our yearly goals, talk about some new AI tools we're trying out, and more.

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 the comments****There are no comments. This is a podcast.

In this episode, we talk about the value of a podcast community, and generally how we're trying to protect ourselves from the internet.

In this episode, we talk about about the impact a recent price change is having on Less Annoying CRM's finances. 

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. 

 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. 

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? 

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.

 In this episode, we talk about Less Annoying CRM's new form builder, and what it means for the business 

In this episode, we discuss using consultants to level up your team.

 In this episode, Rick explains how he's getting more hands on with marketing. 

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?

 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.

 In this episode, we talk about Less Annoying CRM's latest sales experiment. 

In this episode, we talk about takeaways from big snow tiny conf, and more.

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

This is our yearly recap episode!Personal updates from 2023 Tyler Goals from last year

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

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

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 buzzword at LACRM. We complain about X/Twitter.

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. Tyler talks about other ways he's been able to simplify LACRM's operations. Tyler has a coughing fit and we give up early.

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 history of LACRM's product strategy, and what comes next. Rick has a major milestone to share.

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.

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. We spend a while discussing different growth ideas, especially related to sales and outbound marketing.

 In this episode, we talk about how both of us are refocusing on execution. Here's the full topic list: Tyler is trying to focus everyone at LACRM on the top priorities including: Having the devOps team do a bit more normal software engineering work. Offering customer service people a chance to work on marketing and sales. He himself is starting to code again. Rick explains how LegUp Health is focused on execution and it seems to be working. Rick/JD hired a sales coach. Rick talks about what he learned from the book Amp It Up. Tyler poorly explains why LACRM is going to work on a feature that isn't the top priority. We talk a bit about how to optimize a support team Rick is starting to think about how he can contribute to marketing.

In this episode, we talk about Rick's early signs of success getting out a sales rut, and much more.Full topic list: Rick gives an update on how he and JD are getting out of a sales rut. Rick is busy and has absolutely zero free time. Tyler talks about how he's considering web forms and automations as possible features for LACRM. We discuss an alternative approach to freemium. We brainstorm how to use the "engineering as marketing" approach for LegUp Health, but don't really get anywhere.

In this episode, we talk about how much optimization should be done before you have demand generation figured out.Here's the full topic list: Rick is back from parental leave, and he has things to say about what it's like to take care of two kids at once. We discuss what our perfect days look like. Tyler talks about how LACRM had a bit of crunch mode, and how they stayed calm. Rick talks about a sales slump, and what he's doing about it. We talk about how LegUp Health migrated from no-code to full-code. Tyler gives an update on LACRM's growth the first half of the year. We talk about switching from Google Analytics to Fathom. LACRM is considering how to price a feature that has some extra infrastructure costs. Tyler is reconsidering a feature he's been talking about for years. Literally. Years.

In this episode, we talk about what Less Annoying CRM is doing to handle sales tax compliance worldwide.Here are all the topics: Tyler has officially signed the partnership agreement with Rick and LegUp Health! Rick is wrapping up a position/brand/story project LegUp Health has updated their mission and core values Things are a bit hectic at LACRM Tyler is considering merging his personal blog back into the LACRM blog LACRM is probably switching from Stripe to Paddle Rick shares what he's learned servicing the early LegUp Health group insurance clients We talk a bit about ChatGPT and how it can be useful for no-code/low-code apps Tyler rants about how we talk about priorities

In this episode, we talk about Less Annoying CRM's producthunt launch, and a lot more.Here's the full topic list: Tyler takes a look back at LACRM's growth history, and explains their new approach to growth. Tyler explains how the recent Product Hunt launch went. Rick has cleared a lot off his LegUp Health plate and is starting to focus on new types of work. LegUp Health had its first partner meeting. April was a record month for LegUp Health. LACRM has their designer back with more hours than ever. Rick is looking to target CPAs as customers. The LACRM coding fellows have started. We discuss how to deal with the low points of being an entrepreneur.

In this episode, we discuss some changes to LegUp Health, the end of Tyler's sabbatical, and more.Topics in this episode: Tyler is back from his sabbatical LACRM is getting ready to launch a major redesign Rick gives updates on how the LegUp Health/Benefits plan has changed Because of the changes, we renegotiated Tyler's compensation and involvement in the company Tyler talks about the difference building a product that customers don't expect to use regularly vs and every-day productivity tool. Rick gives an update on working with a marketing coach We talk about Seeyafuture.me

Come on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules.

In this episode, we talk about the very early stages of building LegUp Benefits, and a bunch of other stuff. Topics: Rick has hired a marketing coach for LegUp, and we discuss how to get the team talking to each other more instead of having everything flow through Rick. Tyler gives some reflections on leaving LACRM for 6 weeks, and the early days of his sabbatical. Tyler describes a new positioning idea at LACRM. We discuss the early work on LegUp Benefits including customer validation and learning a new tech stack. Rick gives an update on his new group insurance efforts. We talk about Silicon Valley Bank even though we don't have anything to say that hasn't already been said.

 In this episode, we talk about how bootstrappers can win against companies that have raised massive amounts of money.Full topic list: We give an update on the compensation negotiations we discussed last episode. We've agreed on terms for Tyler to work for Rick on LegUp Benefits! Rick had his first annual offsite and shares a ton of great learnings. LACRM had a great month in February. There was absolutely nothing to learn from it. LACRM's major redesign is getting closer. Rick has streamlined bookkeeping and other financial tasks to save time. Tyler is thinking through when it makes sense to do custom work for a large client. We tackle a listener question: How do bootstrapped companies compete with funded competitors.

If you've been following along, you know that Tyler is about to temporarily join Rick's startup to help build their new app. In this episode, we talk about the compensation proposal Rick just came up with. Full topic list: Rick already has a new group insurance client after deciding to give that a shot in the last episode. JD is visiting Rick in Utah next weekend. Tyler is having success with delegation, and finds himself with a lot of unstructured time on his hands... ...and Tyler is having to re-learn what to do with unstructured time. LegUp Health got hit with a bunch of spam contact forms. Tyler is planning the new office layout for LACRM. Apparently design debt is a thing. Tyler is having trouble getting started on the LegUp Benefits project. Side projects are hard. Rick brings up Youtube Premium, Quora, and NotionAI Big topic: We discuss the compensation proposal that Rick just sent Tyler.

 In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more.Topics in this episode: Tyler shares his experience at Big Snow Tiny Conf Tyler is getting ready for a sabbatical which means delegating a lot of work to other people Rick talks about gather customer profiles at LegUp Health Rick explains what "aged leads" are We discuss whether or not it makes sense for Rick to go after group health insurance clients Tyler talks about an LACRM company tradition LACRM launched their Zapier integration! Tyler is preparing to do more design work We have some rants and shoutouts We talk about what to do when a lead asks for security certifications and/or asks you to fill out a questionnaire 

Topics this week: Tyler is going to work with Rick to build the new LegUp Benefits SaaS product Rick has officially transitioned LegUp to 2023 Rick talks about how Airtable Interfaces are useful Rick talks about an annual retreat with JD, and we discuss rituals and traditions Tyler is going to Big Snow Tiny Conf LACRM launched their new API, and are almost ready to launch Zapier integration We talk about the value of podcasting

Full notes to come (sorry, it takes a while to write everything up)

Topics in this episode:  LACRM is having a good December Rick is feeling lots of momentum Rick gives an update on LegUp Health's growth Rick is reading the Warren Buffet bio: The Snowball Tyler explains LACRM's new approach to bug triage Rick is thinking about how hard to push for in-person Tyler describes a new shorthand: Following daylight Rick realizes he's learning a lot about digital marketing We discuss how it's good for businesses to be boring and complex Ricks suggests having "certifications" for new hires We discuss Webflow Logic Rick is going on a date! Tyler is trying to decide how to prioritize big bets vs. small bets at LACRM.