Startup to Last
161 episodes - English - Latest episode: 5 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
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...
The final episode
August 17, 2021 22:13 - 52 minutes - 52.8 MBThis is our last episode. Thanks to everyone who has listened and supported us over the last couple years. We're going to miss you 😢 Topics in this episode: Rick accepted a new job. What does that mean for LegUp Health? Rick finished migrating his help site to Webflow. Rick notified his free users that the free service is shutting down. Tyler talks about compounding and what it means for thinking about the future. We discuss how it might be harder to start a company these days...
Sustainability starts with planning
August 10, 2021 23:00 - 53 minutes - 53.7 MBTopics this week: Rick is canceling his CRM subscription. Tyler is considering where his newsletter fits into his overall plan. Based on our conversation last week, Rick has new clarity around the future of LegUp Health. Tyler explains how LACRM came up with their long-term product roadmap. Rick is going through continuing education. We discuss some touchy feely things related to the passage of time.
What to cut and what to keep
August 05, 2021 22:18 - 58 minutes - 58.6 MBTopics from this episode: Less Annoying CRM is back to remote-first because of the new wave of the virus. LACRM had a new developer start this week. Rick is thinking about how to simplify his business. Specifically, what can he cut? We discuss what it means to be a calm company. Or is that even the goal?
Home runs vs. consistency
July 26, 2021 22:03 - 41 minutes - 43.7 MBTopics from this episode: Tyler hit 2,000 Twitter followers, and we discuss how Twitter is a hits-based business which doesn't suit Tyler's strengths. Rick gives an update on his personal website and newsletter optimization efforts. Rick reached the first page on an important search term. Less Annoying CRM is tweaking the format of help articles to appeal more the the easily distractible internet user. Rick has finished his javascript course. Tyler discusses the LACRM product ...
Throwing things at the wall to see what sticks
July 20, 2021 23:26 - 1 hour - 62 MBTopics this week: Tyler had fun with a once-per-year football bet, and Rick had to put in a full day of dad duty. Tyler is considering taking the ShiftNudge design course to get better at design. He also purchased a license to Tailwind UI so he can copy from better designers. LACRM is tweaking it's policy that everyone at the company must do an hour or support each week. Rick reflects on the value he gets from both writing and reading personal newsletters. LACRM is tweaking it'...
The thing about utopias is that they're not real
July 13, 2021 22:23 - 1 hour - 60.6 MBTopics this week: Rick launched LegUpBenefits.com. We discuss Rick's new no-code tool: Outseta. Less Annoying CRM has a new developer starting next month. Tyler has refined his approach to writing internal documentation, and Rick makes a fantastic analogy. Tyler's co-founder/brother will be in town next week. Rick wants to keep practicing coding so his skills don't deteriorate. Rick is taking a break from podcasts. Tyler wants Rick's help to teach the coding fellows about no...
Sharing profit with employees
July 06, 2021 22:15 - 53 minutes - 53.1 MBTopics this week: Rick took some time off, but is wondering if he earned it. Tyler wrote five blog posts in one day, and wonders if this should be the new approach to blogging. Rick decided to wait for Memberstack updates before taking on a coding project he was planning. Rick is using Outseta for his next technical project to diversify away from Memberstack. He plans to have the done in the next week. Rick is still waiting to decide how to handle the API vendor that closed dow...
When platform risk goes wrong
June 29, 2021 22:17 - 1 hour - 60.8 MBTopics in this episode: Tyler was interviewed to be on Mixergy, but didn't think he did a great job. Rick is adjusting his routine now that he has a kid to take care of. Rick enrolled in a new javascript course to hone his skills. Tyler's previous positive results converting website visitors to his newsletter have turned to failure. No one is signing up. Tyler attended Less Annoying CRM's first leadership team meeting. Tyler had his first person finish building a website based...
When churn and word of mouth cancel each other out
June 22, 2021 22:01 - 46 minutes - 46.8 MBTopics this week: Tyler has a new iPad and doesn't know what it's good for. Rick has added a client through word of mouth, and we discuss how churn and word of mouth are constantly battling with one another. Rick has resolved a major issue one of his clients had with their dental insurance. Crisis averted. Tyler has been working on the wrong things, and is trying to correct that. We discuss Less Annoying CRM's new leadership team. Rick is applying his new javascript skills to ...
What we've learned about podcasting after 100 episodes
June 15, 2021 22:34 - 1 hour - 59.5 MBTyler has a new mic. Tyler is in the middle of the final round of interviews for his new dev hire, and he's starting to plan onboarding. We discuss whether to put a new LACRM content project on the main lessannoyingcrm.com domain, or a separate mini-site. Rick finished taking his javascript course. Rick's dad is in town, and he's taking a bit of time off work. We discuss a trick for getting people to complete online courses. We reflect on what we've learned after recording 100 episode...
Content marketing: Putting all our eggs in one basket
June 08, 2021 22:17 - 54 minutes - 51.3 MBTopics covered this week: We selfishly discuss larger themes we've covered on the podcast which might make for good topics on the Indie Hackers podcast. Tyler's newsletter signups have increased since changing the call-to-action. Rick lost another LegUp Health client due to unavoidable churn. Tyler has a content idea centered around CRM pricing. Tyler wants to do engineering as marketing but doesn't have any good ideas. Rick is almost done learning javascript. Rick has his fi...
What does a $100k/year support person look like?
June 01, 2021 22:18 - 52 minutes - 51.2 MBTopics this week: Tyler asks Rick how he configured the call-to-action for his newsletter on his blog. Tyler is adding a curated list of links to his newsletter. Tyler overcame writers block and wrote his first support-focused blog post. Rick is curious what a highly-compensated support rep might look like at LegUp Health. Rick started paying for Notion. Tyler gives a shout-out to SavvyCal. We take a listener question about how to reach customers who don't have online communi...
Can a course business succeed even if no one finishes them?
May 25, 2021 21:53 - 38 minutes - 36 MBTopics in this episode: Apparently online courses have a very low completion rate, but maybe that's ok? Rick is learning more about javascript and has a few questions. Rick is taking a vacation where he'll fully unplug. Tyler gives some learnings from the recent enterprise deal that LACRM closed. Tyler has the interview process figured out for LACRM's next hire.
Making your first hire
May 18, 2021 23:37 - 59 minutes - 56.2 MBThis week, we answer a few listener questions about how to make your first hire.
When customer expectations aren't met
May 13, 2021 22:17 - 41 minutes - 40.7 MBTopics this week: Rick crossed 200 subscribers for his personal newsletter. Rick gives an update on some recent milestones related to this podcast. Rick has been doing Wes Bos's beginner javascript course and is learning a lot. Tyler is on vacation, and is mostly just taking it easy. We discuss Notion's new API. Rick seriously sprained his ankle. Rick is dealing with a customer who is disappointed.
The Theory of Constraints
May 06, 2021 22:34 - 1 hour - 65.3 MBTopics this week: We're using a tool called ZipMessage to collect listener questions. If there's something you'd like us to discuss on the podcast, leave us an audio recording of your question at zipmessage.com/tyler Less Annoying CRM had a good April. LACRM's average account size is going up slightly, but it's having a significant impact on revenue. We discuss the theory of constraints, and how Rick can apply it to his next project. We talk about interviewing software engineer...
The importance of internal communication
April 29, 2021 22:30 - 1 hour - 67.4 MBTopics this week: An effective, but maybe sleazy tactic for cold emails. LegUp Benefits got its second paying customer. Rick is done with SEO for now, and wrote 35 new pieces of content in April (holy shit!) Rick is focusing on LegUp Benefits for the next six weeks. Less Annoying CRM has finally closed a big enterprise deal they've been working on. Tyler is about to start trying to hire a developer. Less Annoying CRM's office setup is changing, and we discuss the importance o...
Empowering employees to be leaders
April 22, 2021 22:20 - 1 hour - 64.1 MBTopics this week: Tyler gave an internal presentation at Less Annoying CRM and announced a few new things... The office is being reopened in May. There will be a new remote work policy in place. A deep dive into how DEI (diversity, equity, and inclusion) fits into Less Annoying CRM's structure. A new leadership team. Rick is working on content and had a big SEO win. We discuss Roam Research as a possible note-taking tool for Rick. Rick recommends Readwise.io for converting K...
Time management
April 15, 2021 22:17 - 55 minutes - 55.4 MBTopics this week: Tyler is reading a book called Killing Marketing. Rick is trying some time management hacks. Tyler has a potential job candidate using his new approach to recruiting. Less Annoying CRM had their "day of rest" where developers take over customer service for a day. Rick is working on content and SEO for LegUp Health. Rick has filed his taxes. Rick gives a shoutout to a listener that makes software that verifies financial transactions who helped him with a ques...
$2k MRR
April 08, 2021 22:14 - 56 minutes - 57 MBTopics from this week: Rick has a baby! Rick broke $2k MRR in March. Tyler gives an update on his content marketing site. Tyler is about to start recruiting a developer. We talk about all the speculative bullshit going on right now (NFTs, GME, bitclout, etc.). Rick feels pressure to narrow his focus now that he's a father. We discuss how to implement an internal tool with no-code.
Jamming with Dru Riley from Trends.vc
April 01, 2021 18:41 - 1 hour - 53.1 MBYou can learn more about what Dru's working on on Twitter or at Trends.vc.
Deep dive into an execution retreat
March 25, 2021 22:16 - 52 minutes - 52.3 MBBecause Rick is taking some time off for parental leave, we recorded a special episode this week. Rick is about to do a week-long retreat to try to finish a major project before becoming a dad. We're going to spend this episode discussing how he can get the most out of the retreat.
Burnout
March 18, 2021 22:15 - 56 minutes - 57.4 MBTopics this week: Rick is feeling burnt out. We discuss how he noticed, and what he's doing to fix it. Rick's baby is expected this next week, so the next two weeks of the podcast will be pre-recorded episodes. Tyler is drowning in meetings. Tyler gives an update on his new content site. We talk a bit about SEO. Rick is looking for two plugins to help with his Webflow site. We have both received our first vaccine shots, and we discuss what it would look like to re-open an off...
Enterprise sales is just project management
March 11, 2021 23:15 - 59 minutes - 59 MBTopics this week: Rick breaks down how the new stimulus bill will impact health insurance and entrepreneurs. Rick is putting his big project on hold until after paternity leave. Tyler gives an update on Less Annoying Business. We discuss enterprise sales, and how it's more about project management than convincing someone to buy. We talk about Zapier's acquisition of Makerpad.
What does Indie.vc's move mean for startup to last companies?
March 04, 2021 23:22 - 55 minutes - 58.5 MBTopics discussed: Indie.vc is shutting down Rick gives a revenue and churn update. Rick is preparing for the birth of his first child, but has one more big project to finish first. Tyler recaps the first week of results after launching Less Annoying Business last week. We discuss whether it makes sense to build an audience. Tyler is trying to get help with Elasticsearch from his online community. We discuss the long, slow SaaS ramp of death.
Hardcore week building a content site
February 25, 2021 23:19 - 1 hour - 58.9 MBTopics we covered today: Rick finished his goal for February of automating the monthly emails at Legup Health. Tyler gives an update on his new small business advice website. How do you like that link building I just did? Tyler remembers how fast a project can move when you don't have legacy code slowing you down. We discuss a variety of tools used to build a content site, especially Webflow and ConvertKit. Tyler used Fiverr for the first time to hire a designer. We discuss mu...
Content marketing when you're not a domain expert
February 18, 2021 23:30 - 1 hour - 64.3 MBTopics discussed this week: Rick is learning more powerful no-code tricks with Zapier, and advancing his PHP knowledge. We discuss the best way to learn how to write secure code. Tyler is wrapping up a big project which involves setting deadlines. We discuss healthy vs. unhealthy deadlines. Tyler is brainstorming content marketing approaches which is tough because he's not an expert on the topics his customers are most interested in. We discuss Rick's learnings from Peter Druck...
Separating decision making from executing
February 11, 2021 23:28 - 1 hour - 59.1 MBMore topics: We discuss the state of independent SaaS and what it means to have a very low payback period. Rick has installed a development environment and is learning to code again. Tyler is almost done getting ready to switch the LACRM marketing site to Webflow. Tyler is considering trying out Mixpanel. Salesforce is going more remote. What does that mean for San Francisco. We discuss Tyler's tweet thread about his internal dashboards. We talk about the Trends.vc report on ...
Getting marketing ideas from Hubspot's acquisition of The Hustle
February 04, 2021 23:23 - 1 hour - 57.7 MBOther topics this week: Rick officially launched a "give back" program Rick decided not to post internship openings until post-parental leave. Rick wants to start a group focused on reaching local consumers. Tyler is planning an at-home retreat. Morale is a bit low as covid drags on. We discuss a specific UI decision LACRM is facing. We discuss aligning what you want to have happen with what will actually happen.
The paradox of success
January 29, 2021 00:46 - 57 minutes - 54.4 MBOther topics this week: How Robinhood's recent controversy applies to Rick's business model. Rick received his first cancelation. Twitter acquired Revue. Rick is working on a low-code solution to an automation issue. Tyler is close to closing a deal with an enterprise client. We discuss how to handle security audits (e.g. SOC 2 compliance) with enterprise customers.
Is building an audience worth it?
January 21, 2021 23:23 - 1 hour - 60.7 MBOther topics this week: Less Annoying CRM hit $3 million ARR, and the tweet about it got a lot of engagement. Rick paid out referral rewards to his clients. Rick explains his buyer journey exercise. Rick reflects on the value of customer appreciation. Tyler has been a guest on several other podcasts. We discuss how to react when a competitor launches. We discuss the idea of building buffer into everything we do, and how it relates to the startup to last philosophy.
The future of no-code
January 15, 2021 21:04 - 57 minutes - 54 MBOther topics this week: Tyler reviews what he learned from last week's DDoS attack. Rick has planned out the year and feels good about his ability to get it done. Rick is allocating 50% of his time to promotion and 50% to automating his product. Tyler is about to start teaching a design course. LACRM is close to finishing a migration to Webflow. We discuss Clubhouse. Tyler is getting a Peloton. Rick is experiencing anti-depressant withdrawal syndrome.
What it's like to get DDoSed
January 07, 2021 23:35 - 57 minutes - 52.9 MBOther topics in this episode: Trump and his group of domestic terrorists are trying to overthrow the government and it sucks. What a Democrat-controlled government means for healthcare Rick's business is extremely seasonal. We give financial updates from 2020. Rick is working on some tooling changes: Twilio, Front, and knowledge bases. Don't be envious of other people.
End of 2020 mega-episode
December 31, 2020 23:00 - 1 hour - 86.8 MBLooking back at 2020 Note, many of the goals mentioned here were set in our 2019 recap episode. Personal accomplishments Rick 2019 Goal: Get to a point where he and his wife feel comfortable having kids - ✅ Not only are they ready, Rick's wife is pregnant 🎉 2019 Goal: Increase level of play - ✅ He's been playing basketball, skiing, playing water sports, etc. Had success writing his newsletter almost every week. Tyler 2019 Goal: Get a dog - ✅ His name is jolo and he's an i...
Should your startup donate to charity?
December 24, 2020 23:15 - 1 hour - 61.5 MBOther topics: Tyler realized he might have more revenue growth next year than he originally thought. Rick is learning that things don't die down immediately after open enrollment, and that's making it hard to do end-of-year planning. Tyler has been thinking about what the approach might be when LACRM re-opens the office. Rick is meeting his intern for the first time in-person. Rick switched to Notion and is loving it. Tyler has a marketing approach that he wants feedback on. ...
Product Market Fit
December 17, 2020 23:39 - 1 hour - 68.3 MBOther topics from this episode: Rick is finished with open enrollment and walks through some metrics. Rick is expecting his first churn from customers who signed up earlier this year. Rick realizes that word of mouth happens at specific moments in time, such as when someone leaves their job, gets married, or has some other life event. Tyler is learning more about his strengths and weaknesses. Tyler is overwhelmed with interviews. Tyler is preparing a presentation on recruiting...
Celebrating wins in the early days
December 11, 2020 00:05 - 54 minutes - 52.4 MBOther topics we covered this week: Advent of code The Less Annoying CRM design fellowship is finalized. Rick has a few different channels that are showing traction including Instagram DMs and getting referrals from other insurance agents.
Info products moving to a subscription model
December 03, 2020 23:24 - 1 hour - 60.4 MBHere are some of the other topics we discuss: Slack was acquired by Salesforce for a bunch of money. Like, a whole lot. Stripe launched a new "Treasury" product. Tyler finished his end-of-year planning. Rick has been bouncing between projects. Google Search Console has been broken for Rick. My first million is a good podcast.
Planning a marketing sprint
November 26, 2020 23:16 - 55 minutes - 51.2 MBBecause this is a short week, we didn't have many updates. Instead we focused on two main topics: The trend of SaaS companies bundling multiple products into a single subscription. Rick's marketing plan for the next few weeks.
Traction vs distraction
November 19, 2020 23:28 - 1 hour - 59.8 MBSome topics we cover: Rick has been reading two new books that teach about avoiding distraction and staying focused. Tyler had a product strategy breakthrough after giving himself time to think through a bunch of bad ideas first. Rick reflects on his failed startup from last year and we discuss the merits of having a portfolio of products vs a single product to focus on. Rick has been marketing LegUp Health, including making an appearance on tv. Tyler reports on the results of ...
Setting goals when you're just getting started
November 12, 2020 23:43 - 1 hour - 60.2 MBOther topics we discussed this week: Tyler has another lesson to share from the book he's reading. Rick stopped marketing and he's struggling to get momentum back. Tyler is trying to design team permissions for Less Annoying CRM and it's proving to be difficult. We give a shoutout to Jetboost. Rick is frustrated that no-code tools aren't more transparent about their product priorities.
How big to go when moving upmarket
November 05, 2020 23:44 - 1 hour - 65.2 MBOther topics this episode: Tyler is switching Less Annoying CRM to Notion. Rick is finished with outreach to existing customers to prepare for open enrollment. Next up is marketing/sales. Rick's employee Lena is doing a great job executing their content strategy. Tyler gives an update on Less Annoying CRM's financial results in October.
Startup community fatigue
October 29, 2020 22:32 - 1 hour - 62.8 MBSome other topics from this week: Rick is getting ready for open enrollment, and he explains the history behind why health insurance is sold all at the same time in the U.S. Tyler has been talking to customers a lot recently. Tyler is using "revenue per employee" as a simple guide for whether or not LACRM can afford to hire employees. Wildbit shows what it means to "startup to last" after celebrating their 20-year anniversary. Rick is interested in grain.co. Instagram/Facebook...
Offering night and weekend support without burning out your team
October 22, 2020 22:45 - 1 hour - 65 MBSome other topics discussed this week: Rick separated his marketing site from his app and launched a site for his b2b product: www.legupbenefits.com Less Annoying CRM launched a new help site and in-app help center. We discuss what interns can do to get the most out of a remote internship. Rick's ridiculous shoes arrived and they're meh. The lesson is: Don't buy shoes because a company put their logo on them. Rick will yell at me if I don't point out that he didn't get the ones...
The perils of being dependent on a platform
October 16, 2020 00:00 - 59 minutes - 58.4 MBHere are the topics we covered this week: Tyler has to decide between keeping his design consistent vs. optimizing each page's design for the content on that page. Rick has moved into a new house Tyler had his first meeting with the new mastermind group. Tyler gives updates on his ongoing Webflow project. We discuss the upsides and downsides of building a startup on tech platforms (e.g. no-code tools) as well as distribution platforms (e.g. the Shopify app store) We talk about...
Building a moat
October 08, 2020 22:25 - 1 hour - 61 MBHere's what we discussed this week: Tyler gives an update on the 1:1 meetings he's had with his whole team over the last week. Rick launched a digital health tool marketplace Rick is wrapping up his projects from earlier in the year and is ready to focus on a few important things going forward. Less Annoying CRM is close to close two new accounts, each of which are significantly larger than any customer they've had before. Rick complains about his CRM adding data automatically....
Should multiple products share a single brand
October 01, 2020 22:30 - 1 hour - 57.7 MBHere are the topics we discuss this week: The difference between work and hobbies when hobbies involve work topics. Rick is focusing more on outreach. Tyler gave a 6-month presentation to his employees. Rick is about to build his employer-facing product using Glide. Should startups with multiple products put them all under a single brand umbrella, or run separate marketing sites for each one? Rick is switching from Google Meet to Zoom. Should startups ask for a credit card wh...
All-nighters
September 24, 2020 22:25 - 59 minutes - 55.1 MBHere are some topics we discussed this week: Rick was on an entrepreneurship panel at his former high school. Rick has automated most of the onboarding process at LegUp health. Tyler gives an update on his price increase. Rick closed his first employer client and has lots of other opportunities coming up soon. Rick gives shout-outs to The Infinite Game and INTRO (we also discuss Trailhead). We commiserate about Webflow limitations. We talk about smart home devices (what does ...
Handling capacity at a seasonal business
September 17, 2020 23:19 - 1 hour - 62.7 MBHere are the topics this week: Rick is on a roll with his website build-out. Check it out at leguphealth.com and let him know what you think. We talk about mistakes you can make when handing off ownership to employees. Tyler is reconsidering the benefits philosophy at LACRM. Rick is thinking about how to build out an employer-facing app.