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Startup to Last




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.

00:59:12 2022-09-16
Topics 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...
01:03:48 2022-09-02
Topics: 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 rec...
00:59:16 2022-08-19
Topics 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 LAC...
01:05:34 2022-07-28
Topics 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 employ...
00:58:43 2022-07-14
Topics 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 u...
01:06:15 2022-06-28
Topics 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 b...
00:58:52 2022-06-10
Topics 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...
00:50:52 2022-05-27
Topics 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...
01:00:20 2022-05-10
Topics 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...
01:04:50 2022-04-29
Topics 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 struggli...
00:53:02 2022-04-15
Topics 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/pres...
00:57:50 2022-04-01
Topics 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 h...
01:04:27 2022-03-18
Topics 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 i...
00:59:33 2022-03-01
Topics 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 lear...
00:57:25 2022-02-15
Topics 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 d...
01:03:43 2022-02-04
Topics 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 g...
01:24:15 2022-01-21
This 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 fro...
00:52:08 2021-08-17
This 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 ...
00:53:39 2021-08-10
Topics 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 ...
00:58:01 2021-08-05
Topics 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 wh...
00:41:54 2021-07-26
Topics 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 ...
01:00:38 2021-07-20
Topics 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 c...
01:01:07 2021-07-13
Topics 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 fantasti...
00:53:51 2021-07-06
Topics 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 codin...
01:02:06 2021-06-29
Topics 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 previou...
00:46:09 2021-06-22
Topics 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...
01:03:29 2021-06-15
Tyler 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 ...
00:54:33 2021-06-08
Topics 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 anothe...
00:52:46 2021-06-01
Topics 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 ...
00:38:20 2021-05-25
Topics 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...
00:59:39 2021-05-18
This week, we answer a few listener questions about how to make your first hire.
00:41:22 2021-05-13
Topics 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 vacati...
01:04:46 2021-05-06
Topics 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...
01:07:13 2021-04-29
Topics 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 fo...
01:03:41 2021-04-22
Topics 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 in...
00:55:16 2021-04-15
Topics 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 ta...
00:56:30 2021-04-08
Topics 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, bi...
01:16:22 2021-04-01
You can learn more about what Dru's working on on Twitter or at Trends.vc.
00:52:06 2021-03-25
Because 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 t...
00:56:48 2021-03-18
Topics 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. Tyle...
00:59:11 2021-03-11
Topics 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 enterpri...
00:55:54 2021-03-04
Topics 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 Annoy...
01:01:33 2021-02-25
Topics 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...
01:04:07 2021-02-18
Topics 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...
01:01:34 2021-02-11
More 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 marketin...
01:01:12 2021-02-04
Other 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. ...
00:57:22 2021-01-29
Other 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 d...
01:03:42 2021-01-21
Other 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 apprecia...
00:57:33 2021-01-15
Other 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. ...
00:57:28 2021-01-07
Other 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 upda...
01:32:19 2020-12-31
Looking back at 2020Note, 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 wi...
01:04:49 2020-12-24
Other 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 be...
01:12:49 2020-12-17
Other 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 i...
00:54:22 2020-12-11
Other 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. ...
01:04:45 2020-12-03
Here 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. Go...
00:55:09 2020-11-26
Because 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. ...
01:03:25 2020-11-19
Some 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...
01:05:19 2020-11-12
Other 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 ...
01:06:19 2020-11-05
Other 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 ...
01:06:15 2020-10-29
Some 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 "reve...
01:08:45 2020-10-22
Some 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 d...
00:59:53 2020-10-16
Here 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 mastermin...
01:04:24 2020-10-08
Here'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 ...
01:01:58 2020-10-01
Here 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 ...
00:59:21 2020-09-24
Here 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 em...
01:08:11 2020-09-17
Here 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 ...
01:05:49 2020-09-11
Here are some of the topics we covered this week: Tyler is preparing for vacation. Rick has his new CRM set up. Rick is working on his website and isn't sure the right approach to take. Less Annoying CRM hired a new developer. Less Annoying CRM h...
01:10:17 2020-09-03
This week, we had a special guest: Malia Jones. We discussed how to teach no-code to beginners.
00:59:12 2020-08-27
Here are some topics: Rick is taking a vacation which has him considering if his business should be remote-first so he can spend more time outside of Utah. Tyler was on support last weekend and started testing out ways to limit wasteful uses of c...
01:01:44 2020-08-20
Here are some of the topics from this episode: University leadership handling covid this fall. Rick is using Copper CRM. Rick is done with positioning and moving on to making a website. Tyler has pricing and growth updates. Tyler has been learnin...
01:04:03 2020-08-13
Here are some other topics we discussed: Tyler bought a house. Tyler is starting to do some startup mentorship. Rick's interns are gone. Rick has made progress on his positioning work.
01:03:44 2020-08-07
Here are the topics we discussed: LACRM shipped a handful of small improvements the interns had been working on. Tyler gives an update on the price increase. Rick is applying the positioning framework we applied last week which involved competito...
01:12:31 2020-07-30
Most of this week's discussion was about Obviously Awesome by April Dunford. We also gave some updates on the following topics: Now that Rick is fully committed to Legup Health, he's getting used to giving something his all again. Tyler is consid...
01:04:03 2020-07-23
Note from Tyler: I'm sorry that my dog is whining in the background throughout this episode. I'll banish him from my room in future episodes. He's such a wimp.Here are some of the topics from this episode: Tyler's price increase went into effect,...
00:59:13 2020-07-16
Topics discussed in this episode: Tyler's growth is still going strong. Rick is going to write content to build trust with his early leads. Rick created a slide deck to explain his business. Check it out here and let him know what you think. Tyle...
01:03:12 2020-07-09
Here are some topics from this week: Less Annoying CRM was named the #1 CRM by U.S. News and World Report. Tyler restarted employee raises after temporarily freezing them when the pandemic started. Rick now has fully self-serve onboarding. We dis...
00:53:06 2020-07-02
Here are some of the topics we discussed this week: All of Rick's interns are onboarding, and things are going well Rick is building up a bit of sales momentum We discuss whether or not it makes sense to create artificial scarcity by requiring a ...
00:59:01 2020-06-25
Topics from this week: Tyler talks about the reaction he got when telling his customers about an upcoming price increase. Rick launched his referral program. Tyler is working on a new API for LACRM. Rick has finalized the interns he'll bring on t...
01:04:40 2020-06-18
Here are the topics we discussed this week: Rick's interns are acting as a forcing function to keep him more productive. Tyler has decided on a plan for LACRM pricing changes. Tyler has refined how he talks about project priorities with his team....
01:01:25 2020-06-11
Here are the topics from this week: Tyler and Rick both have interns and need to figure out what projects they should be working on. Rick has been working on a client referral program. Tyler is wondering if there's anything for him to do to partn...
01:06:03 2020-06-04
Disclaimer: This is an awkward topic to discuss, but it needs to be discussed. We do not claim to be experts, but we believe that as privileged white men, it's our responsibility to try to learn, challenge ourselves, and evolve. This conversation...
01:01:58 2020-05-29
Here are some of the topics we covered this week: Tyler's interns started and they're keeping him busy. Rick took a vacation over Memorial day weekend and feels refreshed. Tyler has been brainstorming his product strategy more since last week. Ty...
01:00:08 2020-05-22
Here are some of the topics we discussed this week: Rick made his first revenue with LegUp Health Tyler pimped out his home office with a new chair Rick is using Heap for product analytics Less Annoying CRM had a "CRM Coach day of rest" where dev...
00:50:45 2020-05-14
Here are the topics we covered this week: Tyler got a new standing desk. Rick hit a wall with his product. Both Rick and Tyler have interns starting soon. There's a lot of work to do to prepare. Less Annoying CRM had a breakthrough with their dem...
00:55:50 2020-05-07
We tried out a new format in this episode. Instead of picking a deep dive topic and spending most of the time on that, we both had a lot of updates to give, so we spent the entire episode on that. Here are some of the topics we covered: Rick fini...
00:54:04 2020-04-30
The main question we addressed this week was whether Rick should spend his time selling within his personal network (which would be sure to work, but isn't really repeatable or scalable) or start building out a repeatable marketing channel. The m...
01:04:05 2020-04-23
Takeaways from this episode: It's important to separate marketing tactics from strategy. It's possible that specific tactics make sense, but you need to understand why you're doing those things? What's the goal? It's important to focus on a segme...
01:02:38 2020-04-16
Takeaways from this episode: Rick isn't at a point where he needs to figure this out right now. He thought he might need to know this so he could start courting potential employees for the future, but he can do that without knowing the details of...
01:03:12 2020-04-09
There were a variety of different ideas thrown around in this episode. Here are some of the takeaways: Ideally, a healthy remote culture won't just mimic an in-person culture, it will actually take advantage of the unique characteristics remote h...
01:08:54 2020-04-02
Here are some takeaways from this week's episode: There are two common reasons for a manager to feel impatient: someone isn't motivated to work hard, or they're working hard but not getting enough done. The first type is best to avoid entirely by...
00:57:08 2020-03-26
Here are some takeaways from this week's conversation: It's easier to optimize interactions with existing customers rather than new customers who are onboarding because with new customers, every change is more likely to mess up your onboarding fu...
00:50:20 2020-03-19
First off, sorry about the terrible audio this week. This is probably related to the fact that Tyler is recording from his apartment instead of his office due to COVID-19. We'll get this figured out before next week.Here are some takeaways from t...
00:57:55 2020-03-13
This week we take a break from our normal deep dive topics to talk about current events. Between the coronavirus and the stock market volatility, a lot has been happening that could potentially impact our businesses and lives.
01:05:36 2020-02-27
Here are some of the takeaways from this episode: Even if your product is good for a large group of people (all small businesses in this case) it can be helpful to focus on a specific segment rather than "boiling the ocean" because it gets easier...
00:57:05 2020-02-21
Rick's new business is ramping up, and he's starting to think about how he's going to fund it until it's profitable. He definitely doesn't want to give up any equity at this early stage, so he needs to consider non-dilutive options. Here are some...
00:58:10 2020-02-13
The main theme of our discussion was that it's important to understand the objectives of any meeting. Rick helped Tyler narrow the list of objectives down, and now Tyler needs to (1) consider which objectives are most important to him, (2) consid...
00:52:51 2020-02-07
Here are a few takeaways from this week: Identify what your most important work is, and devote most of your time to that. Rick was spending some of his most productive hours on reading and blogging, neither of which are priorities for his busines...
00:57:40 2020-01-30
Here are some takeaways from this week's episode: Marketing can be broken down into two categories: (1) bringing new people into the top of your funnel and (2) optimizing the conversion rates within your funnel. A lot of technical marketing proje...
01:08:24 2020-01-23
Acquiring customers will be different for every business, but there are a few themes we discussed that should apply to almost any business: There are two goals when acquiring early customers: 1) Growing your business, and 2) Learning what works a...
00:59:54 2020-01-17
It's impossible to cover the entirety of this topic in one episode, but there were some key takeaways that should apply to pretty much any startup: A financial model is something that takes inputs (e.g. historic data and assumptions about the fut...
01:02:51 2020-01-09
We considered having this conversation privately, but since almost every business should have a conversation like this, we decided to record it in the hopes that the discussion is helpful for others. As expected, this ended up being a bigger topi...
00:54:45 2020-01-03
Takeaways from our conversation: Starting a new job is stressful, and one of the main goals should be to make the new employee feel safe. One way to do this is to set expectations are that (a) small enough to be achieved over a short time period ...
00:59:03 2019-12-26
This week, we wanted to take some time to reflect on what happened in 2019 and set goals for 2020. We created a series of questions that Rick and Tyler both had to answer. Here are the answers... What happened in 2019? In our personal lives Rick:...
00:56:44 2019-12-19
Takeaways from our conversation: In the early days, a founder can easily offer great customer service just because they're an expert on the topic and are empowered to solve every problem. Rick doesn't need to worry about this at first. For a low ...
00:55:56 2019-12-13
In this episode, Tyler gets Rick’s advice on how to think about redesigning the Less Annoying CRM marketing website. Here are some of the takeaways: There are different types of website redesigns, including: AB testing (iterating pages on the ...
00:59:47 2019-12-06
In this episode as part of some research for his next book, Rick interviews Tyler about his experience with emotions in the Less Annoying CRM workplace. Here are some of the takeaways: There are frameworks out there for emotional intelligence, s...
00:52:06 2019-11-27
In this episode, Tyler seeks Rick’s advice on how to plan the Less Annoying CRM product roadmap for the upcoming year. Here are some of the takeaways: Product roadmap planning is easier when you are able to align to clear company goals and con...
00:55:55 2019-11-21
In this episode, Rick seeks Tyler’s advice on how to approach consulting on the side to fund LegUp Ventures. Here are some of the takeaways: If you need the money, you’ve got to consult or get a jobAin’t no way around it Consulting can b...
00:57:33 2019-11-14
In this episode, we discuss how to think about positioning, packaging, and pricing a second product when you have an existing customer base. Here are some of the takeaways: Be clear about the primary reason you want to add a second product. This...
00:56:53 2019-11-07
In this episode, we discuss how to identify, invite and recruit beta users for your product. Rick uses one of his ventures as an example, and Tyler helps him work through structuring a beta program for his software-enabled service idea. While we ...
00:45:04 2019-10-31
This episode ended up being a brainstorming exercise on how Tyler can increase the acceptance rate of his job offers at Less Annoying CRM. Takeaways include: Survey candidates after they either accept or reject to learn more When someone says no...
00:51:15 2019-10-24
This episode ended up being a brainstorming exercise on how Rick can set high-confidence MVP requirements for his ventures at LegUp. We identified several approaches to scoping an initial MVP: The productized service approach. This is where you ...
00:51:38 2019-10-17
This episode ended up being a brainstorming exercise on how Tyler can increase usage of  Less Annoying CRM’s customer referral program. Tyler may focus in the following areas:  Trying to increase usage of the existing referral program by driv...
00:58:58 2019-10-10
In this episode, we discuss how to reset expectations with stakeholders when things change. Rick shares a challenge he is facing at one of his companies. While we worked through a specific situation, the general concept applies often. Here’s th...
00:34:39 2019-10-03
Here’s what you should know about Rick: Born in Raleigh, NC and grew up in Morganton and Charlotte, NC Went to college at Duke University Majored in Economics and Computer Science Wrestled at Duke Moved to Park City to Ski bum in after graduati...
00:06:50 2019-09-29
In this short bonus episode, we talk a bit about why we started this podcast and what we hope our listeners can get out of it
00:50:36 2019-09-26
This episode ended up being much more about how to increase workforce diversity than how to hire interns. Here’s a quick rundown:  Tyler and his team at Less Annoying CRM want to increase diversity They primarily source candidates via their su...
00:37:00 2019-09-20
Here’s what you should know about Tyler: Grew up in St. Louis, Missouri Went to college at Washington University in St. Louis (“Wash U.”) Majored in Computer Science Became a web developer through side projects and internships Played guitar...
00:55:51 2019-09-05
In this episode, we talk about why we started the podcast, who we think our ideal listener is, and how we plan to grow our audience.After going back and forth, the following framework emerged for marketing a podcast Why did we start the podcast? ...
00:50:50 2019-08-30
In this episode, Tyler helps Rick create a plan to teach himself how to code a web-based application. Rick isn’t sure where to start and asks Tyler for help. Tyler shares best practices he’s learned from teaching more than 15 people how to co...
00:50:11 2019-08-22
In this episode, Rick helps Tyler think through how to roll out a major product redesign for his 20,000 users. Tyler has a plan, but he’s concerned about losing customers through the transition. His biggest roadblock is figuring out how to roll...
00:54:10 2019-08-08
In this episode, Tyler helps Rick evaluate how to build a new software application from scratch. Since Rick is a nontechnical founder, his biggest roadblock is figuring out how to build the application without raising money.After going back and f...
00:46:47 2019-08-01
What’s an employee handbook?Tyler: The topic this week is employee handbooks. This has been on my mind because we redid our whole employee handbook this last spring leading up to hiring some new people. So I rewrote it and put a lot of thought ...
00:44:56 2019-07-25
Tyler: In this episode, we're gonna talk about the pros and cons of remote work, such as when does it make sense for a company to have employees altogether in an office versus fully remote or something in between.Rick: I personally get this all o...
00:49:19 2019-07-18
The role of a small business or startup CEOTyler: In this episode, we're going to talk about what the role of a CEO should be at a small business or a startup. I always hesitate to call myself a CEO, depending on who I'm talking to because it see...
00:40:22 2019-07-11
Tyler: In this episode, we're going to talk about impostor syndrome. Do you want to kind of explain what you had in mind here?Rick: Yeah. So you know this. I left PeopleKeep after 11 years. For most of the time, I was the leader of the company un...
00:39:32 2019-06-29
In this episode, we discussed salary transparency. After some back and forth, we concluded that a company’s salary transparency policy should be based on its personnel strategy. In other words, how you handle salary transparency, whether it's n...