Startup to Last
160 episodes - English - Latest episode: 7 days ago - ★★★★★ - 20 ratingsTwo 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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Episodes
The first step of a flywheel
April 11, 2024 17:47 - 54 minutes - 53.8 MBIn this episode, Rick explains how he’s getting more hands on with marketing.
Sometimes you need to touch the hot stove
March 28, 2024 21:28 - 52 minutes - 49.7 MBIn 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?
When to outsource
February 29, 2024 18:33 - 49 minutes - 48.4 MBIn 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.
Talk to sales
February 15, 2024 21:20 - 39 minutes - 38.4 MBIn this episode, we talk about Less Annoying CRM’s latest sales experiment.
Learnings from a few days of snowboarding
February 01, 2024 19:25 - 46 minutes - 44.9 MBIn this episode, we talk about takeaways from big snow tiny conf, and more.
Profit first
January 18, 2024 21:17 - 50 minutes - 47.2 MBIn this episode, we discuss how Rick is using the “profit first” mindset to manage company finances.
Looking back at 2023 and forward to 2024
December 29, 2023 02:10 - 1 hour - 81.6 MBThis 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 a newsletter most Sundays (27 total) Other updates Built a new house and moved in Had another baby (daughter) Personal g...
DEI isn't dead
December 15, 2023 20:03 - 50 minutes - 47.7 MBIn this episode, we talk about Rick's open enrollment experience, and what LACRM is doing related to DEI (diversity, equity, and inclusion)
Growth is hard
December 01, 2023 01:24 - 57 minutes - 53.7 MBIn this episode, Rick tries to explain to me that there are people who know how to grow businesses, and I stubbornly insist otherwise.
Inflection point
November 09, 2023 22:35 - 51 minutes - 46.8 MBIn 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.
Reducing Friction
October 27, 2023 00:09 - 34 minutes - 31.9 MBThis 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.
Build it and they will come
October 13, 2023 00:49 - 53 minutes - 49.4 MBIn 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.
The pricing change I didn’t want to make
September 28, 2023 19:22 - 42 minutes - 40.7 MBThis 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.
Reorg
August 31, 2023 22:45 - 42 minutes - 40.1 MBIn 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.
Execution eats strategy for breakfast
August 15, 2023 00:27 - 48 minutes - 46.9 MBIn 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 ...
Getting unstuck
July 23, 2023 20:34 - 54 minutes - 50.9 MBIn 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 ...
You can't optimize nothing
July 06, 2023 23:50 - 1 hour - 55.7 MBIn 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 migrate...
Handling sales tax as a SaaS
June 08, 2023 23:54 - 55 minutes - 51.3 MBIn 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 s...
Recapping the Product Hunt launch
May 26, 2023 00:03 - 1 hour - 61 MBIn 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 w...
Pivots and renegotiations
April 23, 2023 16:06 - 1 hour - 60.9 MBIn 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...
Yet another podcast about AI
April 03, 2023 23:39 - 44 minutes - 41.4 MBCome on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules.
An inside look at building a new product
March 23, 2023 16:06 - 57 minutes - 55.3 MBIn 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 v...
How to win against well-funded competitors
March 03, 2023 15:29 - 1 hour - 61.6 MBIn 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. Ri...
The one where we negotiate Tyler’s compensation
February 17, 2023 15:08 - 1 hour - 61.6 MBIf 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 ...
How we deal with security questionnaires
February 03, 2023 01:55 - 1 hour - 59.3 MBIn 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 t...
Something new to announce
January 20, 2023 01:34 - 1 hour - 56.3 MBTopics 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
Looking back at 2022 and forward to 2023
December 31, 2022 22:40 - 1 hour - 94.9 MBPersonal updates from 2022 Tyler Goals from last year ✅ Plan for travel as part of relationship ❌ Build more schedule flexibility Other updates Figured out personal finance plan with Shelly Rick Goals from last year ✅ Reprioritize daily personal health habits ❓Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands) ❌Writing goals Professional updates from 2022 Tyler Goals from last year ❓ Spend more time working, but on my own term...
Big bets vs small bets
December 13, 2022 17:24 - 1 hour - 61.2 MBTopics 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 sugg...
How can founders use the new AI tech?
December 02, 2022 21:17 - 1 hour - 57.1 MBTopics: Rick gives an update on open enrollment Tyler talks about some upcoming product launches including the new Zapier integration Rick is refining his Adwords approach Rick is starting to think about 2023 Tyler talks about project management LACRM had a CRM Coach culture refresh We talk about the recent wave of AI innovation
Professional hater
November 11, 2022 01:43 - 59 minutes - 59 MBTopics this week: I mean, Twitter, obviously Rick gives an update on open enrollment including... Sales so far His misadventures with Google advertising Website positioning and design Tyler gives an update on LACRM's integration project LACRM just went through a process that happens every six months We talk fruitlessly about the potential recession and tech layoffs
An opportunity that comes along once per year
October 27, 2022 23:56 - 1 hour - 56.5 MBTopics from this episode: Rick gives a big update on how LegUp Health is prepping for open enrollment His goal is to be long-term patient, but have short-term urgency He doesn't have enough traffic for retargeting Outreach will be their main lever This weekend is his chance to get everything ready for November 1st Tyler talks about his time at Founder Summit LACRM is thinking about brand marketing instead of just performance marketing Tyler recounts a churn cohort analysis t...
What's priority #1?
October 14, 2022 00:57 - 54 minutes - 53.1 MBTopics this week: Tyler is getting ready for Founder Summit Rick is learning about digital advertising, and we discuss whether tracking people on the internet is a net good or bad thing Tyler gives an update on his NPS saga Tyler talks about a joint webinar he did with ZipMessage Rick describes his chamber of commerce webinar strategy Windfall is opening a Utah office Rick is getting ready to do outreach, but needs to reduce friction first Tyler is making some changes to how...
The marketing tech stack
September 30, 2022 18:36 - 57 minutes - 54.3 MBI (Tyler) am traveling and don't have time to write up show notes, so the other topics in this episode are a mystery. Enjoy!
How much to spend acquiring a customer
September 16, 2022 00:07 - 59 minutes - 56.8 MBTopics this week: Figma got acquired by Adobe AND I DONT WANT TO TALK ABOUT IT I'M NOT CRYING YOU'RE CRYING SHUT UP YOU'RE NOT MY REAL DAD Rick spent a week in Cancun and soaked up some sweet business wisdom Tyler is experiencing a period of calm at work and has done some coding for the first time in a long time LACRM decided not to hire interns next summer Rick and JD planned their marketing blitz Tyler gives an update on his work to make LACRM into a platform for API integra...
The great re-org
September 02, 2022 02:30 - 1 hour - 60.8 MBTopics: LACRM had a great growth month in August, mostly because of expansion revenue. JD, Rick's business partner, is doing a great job. Rick is oscillating between investing in more resources and staying focused. Rick gives an update on his recent local marketing blitz. Tyler is rethinking the customer onboarding flow. LACRM is shifting around their marketing priorities. Rick shares some wisdom from Jason Lempkin. Rick is learning how it's hard to not have authority. Tyle...
Is SaaS getting harder?
August 19, 2022 00:32 - 59 minutes - 55.8 MBTopics this episode: Summer is ending at LACRM and things are going back to normal. Rick attended a company offsite last week, and now he's behind. LegUp Health is planning a local marketing blitz. Tyler gives an update on pay transparency at LACRM. Tyler has been doing some cold outreach to try to find API partners. There's a new VP at Lucid. Tyler talks about how this episode of Default Alive has an interesting take on no-code. Tyler and Rick talk about how it seems like i...
Single points of failure
July 28, 2022 23:59 - 1 hour - 61.7 MBTopics in this episode: LACRM got DDoSed *again* Rick went to some networking events Tyler is ending his newsletter Rick gives a chamber of commerce update LegUp Health is seeing early success with an incentive offer We discuss handling an employee who leaves for an extended period and whether the goal should be to have no single points of failure Rick talks about how intentional assumptions can combat fear Tyler gives an LACRM product-led growth update
Should you hire a marketing agency?
July 14, 2022 23:56 - 58 minutes - 55.2 MBTopics in this episode: Less Annoying CRM hit $3.5 million ARR. Rick and LegUp Health have signed up for several in-person networking events as well as a number of chambers of commerce. LACRM had a new CRM Coach start. Tyler reflects on why his updates haven't been interesting recently, and what that might mean about how he'd feel running a bigger company. Rick got a new client who followed the ideal customer journey. Feels good. Rick is considering working with an SEO contrac...
Healthy urgency
June 28, 2022 23:37 - 1 hour - 64.5 MBTopics this week: Tyler thinks he's finally fixed his audio setup. Rick and Tyler are both having good sales months. Rick actually knows why! We discuss what indicators a SaaS company might look at to tell whether a recession is impacting their business. Rick is getting weekly updates from JD in a new format that is working well. Rick went to a fancy-pants senator's house to schmooze with the big wigs and now he wants to meet more powerful people so that they can laugh at us co...
Prioritizing effectiveness over efficiency
June 10, 2022 00:59 - 58 minutes - 57.1 MBTopics from this episode: Rick has learned more about how to be a good business partner. Rick is prioritizing effectiveness over efficiency. Tyler asks about how best to track marketing ROI. Tyler has an idea for a platform play at LACRM. Another company in LegUp Health's space has been aquired. Tyler gives an argument against delegation. Rick revisits the importance of buffer. Tyler recommends listening to this episode of the IndieHackers podcast.
Charge Less
May 27, 2022 00:10 - 50 minutes - 49.7 MBTopics from this episode: Rick is working on updating and simplify LegUp Health's messaging. LegUp Health is testing out purchasing leads. Rick talks about the next step of his SEO work. Tyler has been listening to customer interviews and learned some things about pricing and features with LACRM. Tyler isn't listening to as many business podcasts. We discuss the blog post: We Need A Middle Class For Startups
Recession?
May 10, 2022 14:37 - 1 hour - 59.6 MBTopics this week The possibility of a recession and how it might impact businesses like ours. LegUp Health just had a competitor acquired. Less Annoying CRM was DDoSed again. Tyler discusses some traction channels he's been considering. Rick asks about virtuous vs. vicious cycles. We discuss the merits of a multi-product business vs a single-product business.
How to be a mentor when you aren't knowledgeable about a topic
April 29, 2022 01:07 - 1 hour - 63.6 MBTopics in this episode: Tyler bought tickets to attend Founder Summit. Tyler is rethinking his investment strategy. A competitor of LegUp Health is going out of business. Tyler is working on renewing LACRM's office lease. LegUp Health is struggling to scale their outreach, so they're going back to basics. LACRM's new design is coming along. LACRM is making pay more transparent internally. Rick wants LegUp to be in the discussion when people talk about health insurance in Uta...
Mission, Vision, and Values
April 15, 2022 03:14 - 53 minutes - 50.5 MBTopics this week: A new employee started at LACRM Tyler is getting ready for lots of interns Rick has been struggling to form healthy habits Rick gives an update on his business partner's work/life balance Tyler finished his cycle of meeting/presentation/1:1s that he does every six months Tyler asks Rick about how to define mission, vision, and values Rick describes a new marketing funnel he found LegUp Health's vision is supported by a recent regulation change
Tools don't solve problems
April 01, 2022 01:25 - 57 minutes - 56 MBTopics this week: Tyler has been extremely busy with meetings, interviews, etc. LACRM hired two new CRM Coaches. Rick took some time off to ski with his family, watched a Duke basketball game, and celebrated his son's 1st birthday. LegUp Health has mixed results sending cookies to try to delight customers. Tyler gives some updates on product-led growth brainstorming from last episode. LegUp Health added some new tools to their workflow to start making things more efficient. R...
Putting together a growth plan
March 18, 2022 00:51 - 1 hour - 60.5 MBTopics from this week: Tyler explains how bug bounties work. Rick discusses the power of incentives. LegUp Health is adding new clients every week, and we discuss how prospecting is working. Rick brags about his new X1 credit card (I swear this isn't sponsored, we don't have nearly enough listeners for anyone to bother paying us for product placement) We discuss how Rick can thank people who help his business. No-work Sunday is a success for Rick. We discuss Jason Cohen's blo...
The importance of patience and impatience when hiring
March 01, 2022 01:22 - 59 minutes - 55.8 MBTopics this week: Tyler is reading The Great CEO Within. Rick shares some early sales wins. LegUp Health is learning about their ICP (Ideal Customer Profile). Tyler has been experiencing ups and downs when it comes to design, but overall has learned a lot the last two weeks. Rick is making Sunday a "no work" day. Less Annoying CRM is hiring, and Tyler thinks there needs to be more of a sense of urgency. Rick has set a quarterly goal, but it's about learning rather than hittin...
Funding your startup with a day job
February 15, 2022 00:51 - 57 minutes - 56.5 MBTopics this week: Rick is close to finalizing a partnership agreement with his first team member. Tyler is excited that LACRM has been shipping a lot of product improvements lately. Tyler has a new productivity hack he's trying. LegUp Health is doing some cold outreach and so far it's working. LegUp Health joined a new business association. Tyler is nervous about some marketing trends even though they haven't become a problem yet. NFTs. What are they? Why aren't we able to un...
Giving early hires skin in the game
February 04, 2022 00:56 - 1 hour - 59.9 MBTopics this week: Tyler is considering going to Founder Summit in Ashville this fall. LegUp Health signed a partnership deal with Pando Labs. LACRM is on a hiring spree. LACRM has a new thriving wage. We discuss whether video testimonials are a good idea. Tyler heard a podcast which made fun of LACRM's design, and this resulted in him getting some design coaching. We discuss how Rick can structure a partnership agreement with his first hire.
Rebirth / Welcoming 2022
January 21, 2022 01:27 - 1 hour - 79.5 MBThis is our annual retro/goal-setting episode. Here's what we cover: Personal updates from 2021 Tyler Goal from last year: ✅Spend more time with family and friends once vaccinated Other updates Started exercising Froze embryos Rick Goals from last year ✅ Get sleep under control ✅ Adjust to being a dad Other updates Wasn't good about exercising Has only been on one date with Sable Professional updates from 2021 Tyler Goals from last year ✅ Get marketing to a point wh...