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EP84 – Contrarian bootstrapper Ian Landsman

Episode description

"Charge more!" "Use content marketing!" "Start with an ebook!"

There's a lot of folklore in the startup and bootstrapping community. Do they all stand up to scrutiny?

This is my interview with long-time SaaS entrepreneur, Ian Landsman.

Show notes Want to contact Justin? Thanks to...

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EP100 – James Clear: improving your life in 2019 with Atomic Habits

January 24th, 2019

1:02:30

James Clear describes how you can improve your life, using small incremental steps that add up to big wins.

Questions we discuss in this episode:

  • How …

EP99 – Ben Orenstein's new startup is focused on pair programming

January 2nd, 2019

1:07:25

Ben is the co-founder of Tuple.app and is running a new course called Habits for Hackers.

★ Looking for a community of bootstrappers?

EP98 – The hard truth about bootstrapping startups (Part 2 with Jason Cohen)

December 17th, 2018

1:10:35
Jason Cohen asks Justin Jackson hard questions about his startup, Transistor.fm, and what it's going to take to go full-time.

This is the second half …

EP97 – Can you bootstrap a company on the side? (Part 1 with Jason Cohen)

December 14th, 2018

32:09
When you're building a startup you have these questions:
  • Should I work on my startup on the side, and grow it slowly?
  • Should I take investment and go …

EP96 – My secret phone call with Hamish

November 23rd, 2018

57:27

Hamish Macpherson is an engineer at Buffer, and was one of the first people to join MegaMaker.

★ Looking for community of bootstrappers?

EP95 – "Programming's gateway drug" with Samantha Geitz

November 5th, 2018

1:07:10
This is a great chat with Samantha Geitz, a Senior Developer at Tighten, and the founder of BetaFish.

Topics in this episode: 
  • Should …

EP94 – Does the old SaaS playbook still work in 2018?

June 11th, 2018

56:40

So many great topics in this episode: 


  • Should developers learn design?

  • Derrick's "viral signup" trick

  • How important is a personal brand?

  • How to promote …

EP93 – SaaS pricing with Patrick Campbell

June 1st, 2018

57:04
I'm building a new SaaS in 2018 with my buddy Jon Buda called Transistor.fm. Now, we're trying to figure out our pricing. We're trying not to pretend we know everything there is to know about running a SaaS.

So, we …

EP92 – 2018 MicroConf guide with Mike Taber

March 15th, 2018

49:11
Mike Taber (Bluetick) and Rob Walling (Drip) started MicroConf in 2011 as a conference for self-funded startups. It's gone from just over 100 attendees to nearly 500. It's become the place for bootstrappers to hang out.

EP91 – Josh Nielsen from Zencastr: software for podcasters

January 6th, 2018

57:51

Josh started out trying to build a "GitHub for music." When that idea didn't pan out, he still wanted to do something with Web Audio and WebRTC. So he started building Zencastr, which gives podcasters the ability to …

EP90 – "Give yourself time." Building a profitable business on the Shopify apps platform

November 18th, 2017

48:25

6 years ago, Bjorn Forsberg built an app called OrderlyPrint for Shopify. His goal was to increase his freedom, and to spend more time with his family. Was able to achieve it? (This is the 5th case study in the Mega …

EP89 – "We never wanted to fire anyone," Natalie Nagele on Wildbit's journey

October 28th, 2017

54:51

Back in the early 2000s, Wildbit was an agency building Flash websites for Philly nightclubs.

Then, in 2007, they launched their first product, …

EP88 – Pippin Williamson from beer money to over $1 million in revenue with WordPress plugins

October 21st, 2017

47:05

Pippin Williamson started out like a lot of us do: building websites for whoever would pay him. He decided to try selling one of his WordPress …

EP87 – How Nick Disabato built a profitable productized service

October 4th, 2017

54:57

It's time for another Mega Profitable interview! This series aims to help founders, like you, get profitable. Learn how Draft went from having $21 in …

EP86 – Mega profitable with Brennan Dunn

September 20th, 2017

54:59

Introducing a new series: Mega Profitable. What's the difference between a founder who is mega profitable, and a product person who's just making a living? Brennan Dunn joins me to talk about his journey.

This episode …

EP85 – Facing your launch fears with Mike Taber of Bluetick.io

August 11th, 2017

44:14

You'll recognize Mike from Startups for the Rest of Us and the MicroConf conference. He's launching a new product called Bluetick.

This episode …

EP83: Laura Elizabeth – unmistakable product validation

April 8th, 2017

44:40

How do you find product ideas that resonate?

Hear how Laura knew there was demand for her project, Client Portal.

Everyone was like: "I want that."

EP82: Adam Wathan is back with a new launch story

December 23rd, 2016

59:10

When we last chatted with Adam Wathan he'd just launched his first book.

His next project is a course called Test Driven Laravel. You won't believe …

EP81: Behind Adam Wathan's $100k book launch

November 1st, 2016

1:06:04

Adam Wathan has always been passionate about learning new things, and sharing what he's learned with the world.

Then he discovered that he could …

EP80: Are we at peak SaaS?

August 12th, 2016

23:24

Should you start a SaaS company in 2016? Does it still make sense to run a SaaS as a solopreneur?

(Originally posted on the MegaMaker podcast)

SaaS …

EP79: Josh Pigford - "We're all winging it"

June 21st, 2016

1:01:53

Josh is the founder of Baremetrics. But he's also just a normal guy. When a relatively well known investor chastised him, it stung.

How does he deal with scrutiny?

Most companies aren’t doing nearly as well as you …

EP78: Nathan Barry - cash flow therapy (Part 2)

April 6th, 2016

31:09

This is part 2 of my conversation with Nathan Barry. In the past four months, he’s taken his burgeoning SaaS company (ConvertKit) from $1 million in annual recurring revenue to $2 million.

That sounds exciting, but it …

EP77 - Nathan Barry – Three years in the desert (Part 1)

April 1st, 2016

34:42

The last time I talked to Nathan, his web app (ConvertKit) had just hit $5,000 in MRR. In this two part series, Nathan describes how they grew that to $182,000 in monthly recurring revenue.

I’m going to start more …

EP76: Tom & Dan get physical with Studio Neat

February 9th, 2016

40:58

Tom and Dan had one of the most successful Kickstarters of 2010 when they released the Glif. But was that enough to launch full-time careers as …

EP75: Jason Zook on why he’s selling his future

September 24th, 2015

42:51

Jason Zook has a different perspective on life and business. He’s not afraid to try weird and crazy business ideas.

In 2008 he started a business called I Wear Your Shirt. Over 5 years he earned over $1 million in …

EP74: Tracy Osborn – launching a Kickstarter, a book, a SaaS!

September 21st, 2015

47:20

If you want to launch your own Kickstarter, write your own book, or build your own web application you’re going to love this episode.

Tracy Osborn is a serious bad-ass who’s done all three! She’s my guest this week.

EP73: Justin Jackson – “How I got into products”

June 26th, 2015

43:45

I was recently on the Chasing Product podcast with Chris Hawkins. Chris is a good interviewer: he asked a lot of great questions about my back-story, and how I got into products.

There’s this independence and …

EP72: Nathan Barry – “The hardest thing I’ve ever done is SaaS”

May 4th, 2015

55:33

After having great success with books and courses, Nathan Barry has shifted his attention to his SaaS: a web application called ConvertKit.

Two weeks ago I announced we finally hit $5,000 in MRR ( http://t.co/p7CY6OATEf

EP71: Des Traynor on the forgotten job of every SaaS product

December 12th, 2014

45:52

Des Traynor is one of my favorite writers and speakers on the topic of SaaS businesses, and jobs-to-be-done.

Notable quotes

“I think not talking …

EP70: Samuel Hulick talks about building Useronboard

November 7th, 2014

1:07:31

Samuel has become the internet’s authority on user onboarding. In this personal and open interview, Samuel talks about how he was able to discover his niche, build an audience, and launch his first product. He also …

EP69: Nir Eyal on how to build habit forming products

October 31st, 2014

51:04

In June of 2013, I was introduced to Nir Eyal through Ryan Hoover. Nir had been blogging a lot about psychology and analyzing what makes a highly …

EP68: Brian Casel on productized services

October 23rd, 2014

55:55

Brian Casel is a bootstrapper with a lot of projects: he has a podcast, a hosting platform called Restaurant Engine, and a new course called Productize.We talked about Brian’s story (from developing WordPress themes, to …

EP67: Mike Rohde is building a sketchnote army

October 2nd, 2014

37:18

Mike Rohde is a designer and an author, but he’s probably best known for illustrating the 37signals books: Rework and Remote. Mike is now building his own products: The Sketchnote Handbook, and the Sketchnote Workbook. …

EP66: Marc-André Cournoyer on making the leap

September 4th, 2014

39:55

Marc-André Cournoyer is a passionate coder and product person from Montreal, Quebec. If you’re a developer, engineer, or technical person looking to make the jump to building products, you’re going to love this one.

EP65: Andreea and building Startup Kit

August 28th, 2014

26:10

Andreea Mihalcea is a dynamic young founder from Romania. Her and her team are building a new product called Startup Kit. I loved her insights into how and why people buy software products. Startup Kit is targeting an …

EP64: Jarrod Drysdale on bootstrapping design

August 21st, 2014

42:04

First, you need to know that Jarrod Drysdale is a good dude. He’s also the author of Bootstrapping Design, and the creator of Cascade.io. He’s smart, and humble, and talented and he has tons of great things to say about …

EP63: Sacha Greif – how things get popular

August 15th, 2014

35:24

Sacha Greif joined me again for a chat on how he marketed Discover Meteor, and why certain blog posts get popular.

Notable quotes

“I’ve always …

EP62: Paul Jarvis is always hungry

August 7th, 2014

38:02

I freakin’ love Paul Jarvis. He’s creative, he’s unique, and he’s Canadian.

Notable quotes

“When you work for yourself, your boss is an asshole” – …

EP61: Nate Kontny says “Solve your own problems!”

July 24th, 2014

43:11

Today’s interview is with one of my favourite people on the internet: Nate Kontny. He’s the solo-founder of Draft, a web application that helps you …

EP60: Hear how Ryan Hoover built Product Hunt in 4 days

July 17th, 2014

41:29

This week’s guest is Ryan Hoover. We’ve been online friends for a few years now. Back in 2013, Ryan invited me to join a new site he’d created called ProductHunt.com. In the last 3 weeks, it’s exploded. He was …

EP59: Dan Norris and the 7 day startup

July 10th, 2014

37:00

Dan Norris is the co-founder of  WP Curve, and the author of  The 7 Day Startup. He gave himself 1 year to build a profitable product. After spending a year on a product called Inform.ly, with no profits to show for it, …

EP58: Garrett Dimon – SaaS isn’t all rainbows and unicorns

July 3rd, 2014

40:43

Garrett Dimon is the founder of Sifter and author of Starting + Sustaining. We talked about finding an idea, validating an idea, and building your product. Our conversation started with this question: “What are the …

EP57: Brennan Dunn talks about the marketing machine

June 27th, 2014

39:19

Brennan Dunn is the go-to guy to talk about marketing automation. He’s build a SaaS, called Planscope, but these days he recommends first-time entrepreneurs build something smaller (like an eBook, or a webinar). He’s …

EP56: Sean Fioritto on succeeding after failing

June 19th, 2014

37:44

Ok, so ages ago I interviewed Sean Fioritto, the author of Sketching with CSS. I like Sean a lot. He’s from Chicago, and he struggled for years trying to build products. Then he wrote this book, and it took off. You’ll …

EP55: Patio11 on promoting your product

April 11th, 2014

56:06

This week you’ll hear from Patrick Mackenzie (Patio11 on the internet), an influential member of the self-funded, bootstrapping community, as well as a high profile member of Hacker News. Patrick is a great guest: he’s …

EP54: DHH on why 37signals is becoming Basecamp

March 17th, 2014

48:46

David Heinemeier Hansson started working with Jason Fried at 37signals about 14-15 years ago. 10 years ago, they created Basecamp, their first SaaS product. This past week they decided to stop using the 37signals brand, …

EP53: Alex Hillman is the king of JFDI

February 22nd, 2014

59:20

Alex Hillman is many things: first, he’s the king of JFDI (he even has the tattoo to prove it). Second: he’s the founder of IndyHall, a co-working space in Philadelphia. Third: he’s Amy Hoy’s partner in 30×500. And …

EP52: Amy Hoy – “Why it’s not about you”

February 8th, 2014

57:14

Amy Hoy is known for her unfiltered, straight-shooting opinions on building product businesses. Her and her husband  Thomas Fuchs have built  Freckle, an awesome time-tracking web app – and have become well known in the …

EP51: Surprise! Brand new episode with Nathan Barry

December 31st, 2013

31:54

Welcome to a brand new episode of Product People: this is the show that exposes you to the scrappy underworld of people creating their own …

EP50: Jakub Linowski of GoodUi.org

October 30th, 2013

31:43

Jakub Linowski  is a Toronto (Canada) based interface designer. He surprised everybody this year (including himself) by releasing a viral hit called GoodUI.org. In this interview we go behind the scenes, and try to …

EP49: No more excuses with Ruben Gamez (part 2)

October 23rd, 2013

30:47

If you’ve been making excuses as to why you can’t build your product, bootstrap your own business, or hire someone on oDesk? Well you need to listen to this episode because Ruben Gamez here to destroy all those …

EP48: Ruben Gamez thinks about business differently (part 1)

October 16th, 2013

27:01

Ruben Gamez is one of the most thoughtful and wise entrepreneurs I’ve met. He has some great advice on outsourcing, staying focused, getting work …

EP47: Meat and potatoes with Chase Reeves (part 2)

October 9th, 2013

38:25

This week I get into the meat and potatoes with Chase Reeves. This is part 2 of our discussion.

This week we talk about that struggle of building products, especially when you’re just starting out, and trying to figure …

EP46: Chase Reeves has important things to discuss

October 2nd, 2013

40:32

This week, I’m joined by a man. A man named Chase Reeves. We’re going to talk about the business they’re building over there at Fizzle.co.

Chase and I both like to talk, so this is a two-parter! This is part 1.

EP44: DHH at 200 miles per hour (part 2)

September 18th, 2013

24:49

In our last episode we talked about how David started working as a contractor for 37signals making $15 an hour. He eventually worked his way up, and became an owner in the company (along with Jason Fried). In this …

EP43: DHH, a personal interview (part 1)

September 11th, 2013

29:50

David Heinemeier Hansson started working with Jason Fried as a contract worker from Denmark. How did he eventually become a partner at 37signals?

I’ve kept in touch with David over the years, and we’d planned on doing …

EP40: Allan Branch on leaving LessConf to focus on his product

August 21st, 2013

39:36

If you’ve dreamed about building your own product, you’re in the right place. This week the hilarious, talented, and honest Allan Branch joins us to talk about why he’s leaving LessConf behind to focus on LessAccounting.

EP39: Spencer Fry part 2

August 14th, 2013

33:09

Spencer Fry built his first product when he was 19, and now’s building a new product called Uncover. It’s a big risk: it’s an HR product, which is a …

EP38: If Spencer Fry could go back in time…

August 7th, 2013

39:23

What were you doing when you were 19? Spencer Fry built his first online product.

Sponsors

This show wouldn’t be possible without these great …

EP37: Dan Norris gets the Claff

July 31st, 2013

36:54

Imagine building a product for a whole year, and then deciding to try something new on a whim. You build it in a weekend, and in 4 days you already …

EP36: Dan Norris gave himself 1 year to build a profitable product

July 24th, 2013

40:52

Imagine this: you sell your web consultancy, and give yourself 1 year to build a product. You decide to do everything by the book: you’re going to …

EP35: Noel Tock on building products on WordPress

July 17th, 2013

27:14

This is part 2 of our interview with Noel Tock. He built a SaaS app on top of WordPress. In part 1 we talked about the thinking behind that, in part 2 we talk about the lessons he’s learned along the way.

Sponsors

EP34: Building your app on top of WordPress with Noel Tock

July 10th, 2013

24:56

If liked our episodes on using WordPress to build your web app’s MVP, you’re going to love this interview with Noel Tock, of HappyTables.com.

EP33: Jason Calacanis of Inside.com talks about bootstrapping vs funding

July 3rd, 2013

25:21

It’s part 2 with Jason Calacanis!

In this episode we explore the question every product person needs to answer: should I bootstrap, or should I get …

EP32: Jason Calacanis at 300 BAUD

June 26th, 2013

33:43

Normally we cover bootstrapped products: people who are self-funding the stuff they build. We do this because I’m naturally drawn to bootstrapped companies.

For this episode I wanted to go into “enemy” territory: I …

EP31: Dan Martell gives us some Clarity

June 19th, 2013

39:58

Dan Martell discovered computers in rehab. After he overcame his problems with drugs, he taught himself to program. From there, he started building businesses. Eventually, he travelled to San Francisco to learn …

EP30: Dan Martell’s story – from rehab to San Francisco

June 12th, 2013

42:32

Dan Martell discovered computers in rehab. After he overcame his problems with drugs, he taught himself to program. From there, he started building businesses. Eventually, he travelled to San Francisco to learn …

EP29: Cease and desist with Cody Brown

June 5th, 2013

31:51

Imagine this: you build a product that you’re passionate about. To demonstrate it’s capabilities, you create a demo that attracts the attention of the New York Times legal department; who promptly send you a cease and …

EP28: Draw your own video games

May 29th, 2013

28:34

Hey, let me ask you a question: when you were a kid, after a game of Mario Brothers, did you ever take out a pencil and paper and try to draw your own video game levels? The idea of creating video games from a kid’s …

EP27: Does Amy Hoy get scared? (part 2)

May 22nd, 2013

50:48

In this episode of Product People: does Amy Hoy still get scared before a launch? How do you choose an audience? And she answers some listener …

EP26: Amy Hoy sells her My Little Ponies

May 15th, 2013

51:57

Amy Hoy gives a personal interview on her growing up in suburban Maryland, programming on an Apple IIc, selling her My Little Ponies to buy a Power Mac, and how she ended up building her first products.

Highlights

“I …

EP25: Hiten Shah “Make your idea a reality” (part 2)

May 8th, 2013

37:08

Hey Product People! What’s your process for finding an idea that people love? How do you take your initial hunch for an idea, and make it a reality? What is a funnel? Hiten Shah from Kissmetrics is back to answer these …

EP24: Hiten Shah – “Make things that people love”

May 1st, 2013

38:52

Can you build a healthy software business when you don’t know how to code? Hiten Shah is on the show today. He and his co-founder Neil Patel, have …

EP23: Paul Farnell, how does growth happen with a SaaS startup?

April 24th, 2013

35:33

On the show today is one of the best bootstrappers in the business:  Paul Farnell of  Litmus.com joins me and shares some great stories.

EP22: Paul Farnell of Litmus on building a startup in a college dorm (part 1)

April 17th, 2013

46:07

On the show today is one of the best bootstrappers in the business: Paul Farnell of Litmus.com joins me and shares some great stories.

Highlights

EP21: John Saddington on deadlines, partners, ugly babies and warning bells (part 2)

April 10th, 2013

43:22

This week we have part 2 of our interview with John Saddington that literally sent warning bells blaring through the 8Bit office. We also hear about his new Kickstarter campaign:  Pressgram (an iOS app that allows you …

EP20: John Saddington of 8Bit on his adventure as an entrepreneur

April 3rd, 2013

30:27

Before this interview we thought John Saddington was a guy that built WordPress products with his team at 8Bit (we were also intrigued by his new Kickstarter campaign: Pressgram). What we didn’t realize is that John, at …

EP19: Jason Evanish shares his process for understanding customers

March 27th, 2013

30:27

Jason Evanish has made a name for himself as a customer-focused entrepreneur. He caught the eye of  Hiten Shah, the founder of  KISSmetrics. Hiten asked Jason to leave Boston, and move to the Valley to become …

EP18: Jason Evanish moves to San Francisco

March 20th, 2013

36:10

While in Boston, Jason Evanish made a name for himself as a customer-focused entrepreneur. He caught the eye of  Hiten Shah, the founder of KISSmetrics. Hiten asked Jason to leave Boston, and move to the Valley to …

EP17: Nathan Barry shows you how to write, price and sell your ebook (part 2)

March 13th, 2013

40:44

Nathan Barry has released two really successful ebooks, and a new web app called  ConvertKit. If you’ve ever wanted to write your own ebook, but …

EP16: Nathan Barry’s story; building iPad apps, ebooks and web apps (part 1)

March 6th, 2013

40:43

Nathan Barry is an amazing individual: when you spend time with him you can’t help but be inspired to create and launch your own stuff. As a young man he’s had tremendous success is releasing his own products: an iPad …

EP15: Jason Fried on making money, internet fame, and the new Basecamp

February 27th, 2013

36:32

This week we have Jason Fried of 37signals on the program. We discuss how he made thousands of dollars in high school, why he chose DHH as a partner, …

EP14: Kyle Fox on launching, metrics, and lessons learned (part 2)

February 20th, 2013

42:19

Kyle Fox is back for another episode: this time he talks with Justin about the power of design, how big their launch mailing list was, and why it’s …

EP13: Kyle Fox on building his own SaaS app

February 13th, 2013

40:30

Kyle Fox is a real Renaissance man. Besides co-hosting this podcast, and working as a Product Manager at Granify, he also runs his own SaaS app on the side: FotoJournal. FotoJournal allows photographers to create a …

EP12: Brennan Dunn on startup launch tactics (part 2)

February 6th, 2013

44:40

Learn Brennan’s trick for identifying a good market: “find a community, and just keep adding value.” Whether that’s a forum response, blog post, info-product, or SaaS app, learn how choosing an audience and sticking …

EP11: Brennan Dunn on building his startup, Planscope

January 30th, 2013

35:02

How do you make a name for yourself, and your product?

That’s the question we posed to Brennan Dunn.  It seemed like almost overnight he was everywhere: blog posts on Hacker News, popping up in my Twitter stream, and …

EP10: Rob Walling – outsource on oDesk, find your idea, market your product (part 2)

January 23rd, 2013

36:52

Have you ever wondered how much personal brand affects software sales? Check out this is great episode with Rob Walling. In our interview he reveals a ton of tactics for outsourcing your development on oDesk, finding a …

EP09: Rob Walling – Get off the hamster wheel, build your own products!

January 17th, 2013

35:34

Rob Walling is the man behind products like HitTail, DotNetInvoice, and Drip. But he also helped start a movement of micropreneurs: solo-founders, …

EP08: Sacha Greif on choosing a co-founder and building MVP

January 9th, 2013

40:04

This is part 2 of our interview with Sacha Greif. In this episode we talked with him about how to find a partner, and the pain involved in building …

EP07: Creating info-products with Sacha Greif (part 1)

January 2nd, 2013

38:01

What are some good strategies for creating, pricing and selling an ebook? In Part 1 of our interview with Sacha we discuss what he learned launching his first book, and what he plans on doing next time. We also take a …

EP06: Patio11 on building products that make money (part 2)

December 26th, 2012

45:53

Want to build a software product that actually earns income?

In this (Part 2) episode Patrick McKenzie (Patio11) shares specific tactics for …

EP05: How Patio11 built a product business (part 1)

December 18th, 2012

31:57

Part 1 of our interview with Patio11 (Patrick McKenzie) where you’ll hear how he actually learned to program with graph paper, and how he built his first product business with $60.

Show notes:

Patrick’s blog: 

EP04: MVP apps with WordPress (Part 2)

December 12th, 2012

35:26

WordPress was first for pure blogging, then became embraced as a CMS (though some people still deny this), is seeing growth and innovation in being used as an application platform (I think we’re about a third of the way …

EP03: Building MVP apps with Wordpress (Part 1)

December 5th, 2012

34:40

Are you a developer who wants to cut down the amount of time it takes to build a prototype? Are you a product person who can’t code? Do you have a product idea that you want to validate quickly?

If any of those …

EP02: Who should you build products with?

November 17th, 2012

40:42

In this week's call Kyle and Justin talk about people: specifically, the people you choose to build a product with.

There are two ways to look at …

EP01: Our first phone call

October 15th, 2012

29:23

This isn’t a podcast, it’s our first Skype call! As a result, it’s definitely a bit rough, but we think it will give you a good idea of who we are, …

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