Startup to Last

Startup to Last
Two founders talk about how to build software businesses that are meant to last.

Offering night and weekend support without burning out your team
Oct 22 • 68 min
This week, we talk about how you can hire talented support people to work nights and weekends without hating their jobs.
The perils of being dependent on a platform
Oct 15 • 59 min
This week we discuss the upsides and downsides of building on a platform you don’t control.
Building a moat
Oct 8 • 64 min
This week, we talk about how Less Annoying CRM uses customer service as a moat, and several other topics.
Should multiple products share a single brand
Oct 1 • 61 min
This week, we discuss whether Rick should launch his b2b product under the same brand as his b2c product
Sep 24 • 59 min
Rick is on a roll with LegUp Health, and he’s burning the candle at both ends.
Handling capacity at a seasonal business
Sep 17 • 68 min
This week, we talk about how Rick is preparing for his busy season which starts in November
Pricing annual plans when users are added mid-year
Sep 10 • 65 min
This week we dive into how Rick could price his b2b service.
Learning no-code
Sep 3 • 70 min
This week, we talk all about no-code: What it is, what it can be used for, and how to learn it.
Networking without being annoying
Aug 27 • 59 min
This week, we discuss networking (both online and in person) and how to use it in a non-annoying way to make sales. Spoiler alert: Maybe it’s not possible.
What if you get hit by a bus?
Aug 20 • 61 min
This week, we discuss when a startup should start putting together plans for losing a founder and much more.
How college students can prepare for entrepreneurship
Aug 13 • 64 min
This week, we answer a listener question about what college students can do to get ready for startup life.
The Sims, but way more boring
Aug 7 • 63 min
This week, we spend most of the hour giving updates on things we’ve been working on, including LACRM’s decision to use Sococo.
Product positioning
Jul 30 • 72 min
This week, we discuss the book “Obviously Awesome” which provides a framework for how startups can figure out their positioning.
Asking for too much info during signup
Jul 23 • 64 min
Rick has heard feedback from his early customers that they’re apprehensive about the amount of info he’s asking from them during the signup process.
Building trust when you’re an unproven business
Jul 16 • 59 min
This week, we talk about how Rick can convince his customers that he’s trustworthy even though his business is so new that he doesn’t have a proven track record yet.
Winning awards
Jul 9 • 63 min
This week is all about the updates. Less Annoying CRM won a big award, and as always, there’s plenty of intern talk.
The dummy curve
Jul 2 • 53 min
This week Rick gives updates on his sales efforts and intern projects
A price increase is coming
Jun 25 • 59 min
This week we talk about Tyler’s pricing change and a bunch of other stuff
How should a self-serve SaaS handle inbound enterprise leads?
Jun 18 • 64 min
This week, we discuss a listener question about how to handle enterprise leads if you don’t have sales experience.
Curiosity or conviction
Jun 11 • 61 min
This we talk about intern projects, Rick’s decision to stay focused on Legup Health, and more.
Jun 4 • 66 min
Because of the murder of George Floyd and the protests in America right now, we’re taking a break from our normal format
Weighing options
May 29 • 61 min
This week, Tyler talks about the new interns and Rick discusses a potential new opportunity that fell into his lap
First revenue in the bank
May 21 • 60 min
Rick sees his first revenue with LegUp Health, and Tyler has some new ideas about how to think about Less Annoying CRM’s product roadmap
The interns are coming
May 14 • 50 min
Tyler has an army of interns starting next week, and Rick just hired his company’s first
It’s all about the updates
May 7 • 55 min
In this episode, we discuss PPP, taxes, winding down an old company, what types of optimizations are good for the customer, and more.
The first 100 customers for a B2C company
Apr 30 • 54 min
This week, we talk about how a B2C company should go about acquiring its first 100 customers. Rick is shifting his focus towards growth, and he needs to decide how to spend his time.
Marketing during a recession
Apr 23 • 64 min
This week, we talk about how to market during a recession. When people aren’t buying new things, what can you do to get yourself in front of the right people so that they’ll be ready to buy when things get back to normal.
Attracting and compensating operating partners
Apr 16 • 62 min
This week, we discuss what Rick can do to give his early employees a share of the upside without giving away equity
Building remote culture
Apr 9 • 63 min
This week, we talk about how to facilitate building and strengthening relationships between coworkers at a remote company
Dealing with impatience as a founder
Apr 2 • 68 min
This week, we talk about how a founder or manager can deal with impatience. When you have a vision and it’s taking longer than you’d like for it to turn into reality, that can cause problems with the company culture.
Optimizing a customer service team
Mar 26 • 57 min
This week, we talk about how to enable a customer service team to spend as much of their time on high-value conversations that really help customers, and less time on conversations that provide no value.
Writing a startup manifesto
Mar 19 • 50 min
This week, we discuss how and when to write a manifesto for your startup. What are the reasons to write one, who should the audience be, and what can you do with a manifesto once it’s written?
Coronavirus and the stock market crash
Mar 13 • 57 min
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.
Industry-specific marketing
Feb 27 • 65 min
This week, we talk about how to segment your total audience and design a marketing campaign for a specific industry
Raising non-dilutive funding for your startup
Feb 20 • 57 min
This week, we discuss options for funding a business without dilution (i.e. giving up equity). From pitch contests and grants to consulting on the side, we walk through all the different options and weight their pros and cons.
Running one-on-one meetings with employees
Feb 13 • 58 min
This week, we talk about how to structure periodic meetings with employees. How often should they be, what format should you use, and what are the objectives?
Structuring your time to maximize productivity
Feb 6 • 52 min
This week, we’re going to talk about how to structure a week in a way that allows you to spend your most productive time on your most important work.
What programmers can do to help with marketing
Jan 30 • 57 min
This week, Rick gives Tyler some advice on how to make the most of his work retreat. Specifically, Tyler is a programmer who wants to build tools to help the marketing efforts at Less Annoying CRM, and Rick will suggest how those tools can fit into a…
How to acquire customers in the early days
Jan 23 • 68 min
This week, we talk about one of the most fundamental issues that every startup faces: how to acquire customers in the early days. Rick has validated his idea for Legup Health and now it’s time to go out and bootstrap his way to profitability
Building a simple financial model
Jan 16 • 59 min
This week, we discuss financial models. What are they for, what should be included in them, and how sophisticated to they need to be for different types of businesses?
What it means to startup to last
Jan 9 • 62 min
This week, we go all meta and discuss what “startup to last” actually means. Why did we name the podcast this, and what characteristics do “startup to last” companies have in common?
Onboarding a new hire
Jan 2 • 54 min
This week, we talk about how to offer a great experience during a new hire’s first few weeks. Tyler is about to have a new employee start, and he’s looking for ideas on what he can do better.
Looking back at 2019 and forward to 2020
Dec 26, 2019 • 59 min
Because this is the last week of the year, we’re going to summarize what happened in 2019 and set goals for 2020.
Delivering awesome customer service for a low ARPU product
Dec 19, 2019 • 56 min
This week, we talk about how Rick can use customer service as a differentiator for his new company despite the fact that he won’t be making much money per customer
Planning a marketing site redesign
Dec 12, 2019 • 55 min
This week, we talk about redesigning Less Annoying CRM’s marketing site. Tyler’s company just finished a major redesign of the app, and now the marketing site doesn’t do it justice. Rick gives advice on how to approach the project.
The role of emotions in business
Dec 6, 2019 • 59 min
This week, we talk about a topic that Rick is researching for his book: how can emotions help and hurt business leaders?
How to balance building new features vs. maintaining existing ones
Nov 27, 2019 • 52 min
This week, we talk about how to balance competing goals when it comes to product development: how much time should you spend building new features vs maintaining old ones? Tyler’s company is wrapping up a major project and he’s trying to figure out how to…
Should you consult on the side while launching a startup?
Nov 21, 2019 • 55 min
This week, we talk about whether or not it makes sense to use consulting revenue to bootstrap a business. If so, what’s the right way to split time between consulting and your startup?
How to price and position your second product
Nov 14, 2019 • 57 min
This week, we’re joined by Ben Orenstein, co-founder of and co-host of The Art of Product Podcast. We discuss how to think about offering a second product to an existing customer base. From pricing, to positioning, to whether or not a second…
Getting beta testers to use your product
Nov 7, 2019 • 56 min
Rick is almost done with the prototype of one of his new product ideas, and now it’s time for him to get people to start using it. This week, we talk about getting users, motivating them to participate in the beta test, and learning based on their…
How to get job candidates to accept an offer
Oct 31, 2019 • 45 min
Tyler is in the middle of a recruiting cycle and he’ll start giving job offers soon. This week, we talk about what he can do to to increase the odds of candidates accepting those offers.
How to know when a product is minimally viable
Oct 24, 2019 • 51 min
This week, we talk about how “viable” an MVP actually needs to be before you can stop building, and start selling.
How to improve a customer referral program
Oct 17, 2019 • 51 min
This week, we talk about how Tyler can get his customers to use his company’s referral program so that it’s easier to track word of mouth growth.
Resetting stakeholder expectations when things change at your business
Oct 10, 2019 • 58 min
Change is a given at every business and organization. This week, we discuss how you can get all the stakeholders on board when circumstances have changed, and expectations need to change with them.
Interview with Rick Lindquist, founder of LegUp Ventures
Oct 3, 2019 • 34 min
This week we’re mixing the format up a bit. Instead of doing a deep dive on a specific topic, Tyler interviews Rick to learn about how he went from an entry level salesperson to the CEO of a startup that grew to over 50 employees, and what he’s doing now…
Why we started this podcast
Sep 29, 2019 • 6 min
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
How to recruit interns
Sep 26, 2019 • 50 min
This week, we discuss how to recruit interns, especially from non-traditional backgrounds.
Interview with Tyler King, co-founder and CEO of Less Annoying CRM
Sep 20, 2019 • 37 min
This week we’re mixing the format up a bit. Instead of doing a deep dive on a specific topic, Rick interviews Tyler to learn about how he bootstrapped a business to over $2.5 million in revenue, what the future holds, and how he approaches business in…
How to market a podcast
Sep 5, 2019 • 55 min
This week, we take a look inward and discuss what we can do to get more listeners for this podcast. We discuss how to identify an ideal audience, customer development, and more.
How to teach yourself to code a web-based application
Aug 30, 2019 • 50 min
This week, we talk about how an entrepreneur without a technical background could teach themselves to code well enough to build an MVP (minimum viable product) for a web-based SaaS app.
How to communicate major product changes to your users
Aug 22, 2019 • 50 min
This week, we talk about two of the main things to consider when communicating upcoming product changes to your users: how tell a story to generate excitement, and how to make sure that your change-averse users don’t get angry and leave.
How a non-technical founder can make their first technical hire
Aug 8, 2019 • 54 min
In this episode, we talk about how a non-technical co-founder can launch a software product. What are the possible ways to bring on technical talent whether it be as a co-founder, a first hire, or by outsourcing?
How an employee handbook can help with recruiting
Aug 1, 2019 • 46 min
This week we talk about what type of information should go in an employee handbook, and how that content can be repurposed to help with recruiting.
Working remotely vs. working in an office
Jul 25, 2019 • 44 min
Rick and Tyler talk about the pros and cons of a company having a remote workforce vs. having everyone working in the same office.
The role of a CEO
Jul 18, 2019 • 49 min
In this episode we talk about Rick’s customer development efforts, Tyler’s new mastermind group, and what the role of a CEO should be as a company grows.
Impostor syndrome and fear-based decision making
Jul 11, 2019 • 40 min
In this episode we talk about about making decisions under pressure, and how fear can lead to mistakes. The topic started out as “impostor syndrome” and turned into something that neither of us really expected.
Salary transparency
Jun 29, 2019 • 39 min
The topic this week is salary transparency: when does it make sense for a company to share salary information with all employees, and when does it make sense to keep that information private. We dive into how transparency can impact morale and culture,…