Bootstrapped Stories – Details, episodes & analysis

Justin Welsh is the indisputable “King of LinkedIn” — he’s grown to 300K+ followers and more than $2M in online income, in just 3 years.

His business is built like a machine — he’s set up systems for himself that allow him to consistently publish content, lead an audience into his newsletter, and generate revenue through a variety of different channels.

Best of all? He does it all by himself, as a one-man-show.

In this episode, we chat with Justin about his content strategy, his business, and his marketing funnels. There’s a lot to unpack in this episode — get ready.

⏱ What you’ll find and when:

00:00 Intro
03:09 Overview of Justin’s different income streams
07:18 Justin’s $2M marketing funnel
12:20 Going from LinkedIn to Twitter and beyond
14:47 Building a lifestyle business
18:50 How Justin built his audience from scratch
21:26 Justin’s 7-step content production system
28:27 How to build deep relationships with other creators
36:42 When is the right time to start a newsletter?
39:19 How do you find your niche?
42:00 Justin’s mindset on comments and engagement
44:25 Flash questions

🔗 Connect with Justin:

LinkedIn: https://www.linkedin.com/in/justinwelsh/
Twitter: https://twitter.com/thejustinwelsh
Website: https://www.justinwelsh.me/
Instagram: https://www.instagram.com/thejustinwelsh

How do you balance being a high performer and not burning out? What is burnout, anyway? How do you know if you’re burnt out and how can you prevent it?

Sherry Walling, clinical psychologist and author of “The Entrepreneur’s Guide to Keeping Your Sh*t Together” talks to us about mental health as an entrepreneur and high performer.

We speak about balancing working hard and resting, how to prevent burnout, how to understand your capacity, and balancing family life and entrepreneurship, especially with kids.

⏱ What you’ll find and when:

00:00 Intro
02:30 How Sherry helps entrepreneurs with their mental health
04:48 Why is mental health so taboo for entrepreneurs?
06:38 How should entrepreneurs manage their mental health?
08:20 What is burnout and how do you prevent it?
13:31 How do you get high performance without risking burnout?
18:15 How Sherry prevents herself from burning out
23:39 Balancing business with family and kids
33:25 How much time should you work? How do you organise your time?
38:14 Sherry’s new book: Touching Two Worlds
42:01 Flash questions

🔗 Connect with Sherry:

Twitter: https://twitter.com/sherrywalling
Website: https://www.sherrywalling.com/
ZenPodcast: https://zenpodcast.com/
Sherry’s Book: http://touchingtwoworlds.com

Can you be a CEO with no meetings at all?

How do you run a remote-first company successfully? What’s the mindset you need to have?

Amir Salihefendic shares with us his journey growing Doist as a fully remote company to $20M in ARR, while having almost no meetings in his calendar at all.

We learn his mindset on async communication and high-trust environments, and his challenges in growing his company.

⏱ What you’ll find and when:

00:00 Intro
01:14 Growing Doist
07:20 Amir’s mindset on setting business goals
12:30 Todoist’s growth timeframe
15:45 Levelling up early employees
21:01 How to create an async-first environment
26:29 The importance of trust in a remote environment
29:23 What it’s like to have no meetings at all
32:44 Challenges in growing Doist
38:46 Dealing with churn
42:22 How he would do things differently
43:34 Flash questions

🔗 Connect with Amir:

Twitter: https://twitter.com/amix3k

Doist: https://doist.com/

Thinking of launching a podcast for your business or for yourself, but don’t know where to start?

How do you choose your topic? What’s the best podcast format? How do you grow your audience? Moreover, is launching a podcast even the right move for your business?

Understand everything about podcasting in this episode with Justin Jackson, founder of Transistor.fm, a podcast hosting platform used by 20K+ podcasts worldwide.

We talk about how to get started with podcasting, the equipment you need, the topic or niche to choose, how to do SEO research for podcasting, and how Justin benefited from podcasting for his business.

⏱ What you’ll find and when:

00:00 intro
07:36 getting started with podcasting
14:13 the equipment you need to start
18:24 how to choose a topic that will be successful
24:34 SEO tools for podcasts?
32:25 impact of podcasting on Justin’s business
38:52 a little bit about affiliate marketing & support
55:02 do you go on customers’ podcasts?
61:02 flash questions ⚡️

🔗 Connect with Justin:

Company: www.transistor.fm
Twitter: https://twitter.com/mijustin
LinkedIn: https://www.linkedin.com/in/justinijackson/

How do you build a loyal audience before you launch your SaaS business? How do you engage with others in the right way? How do you get the highest impact on YouTube? Moreover, how do you stand out in a competitive social media landscape?

In this episode, Simon Høiburg, founder of FeedHive and content creator (20K YouTube, 25K Instagram) talks to us about growing on social media. We understand how to authentically give out value and grow by engaging with others, and Simon reveals his strategy to get to 100K on YouTube 👀 If building an audience is something that you’re struggling with or need some extra inspiration on, this is definitely the episode to listen to.

📚 Resources Mentioned:

• Podcast: Build to Sell Radio: https://builttosell.com/radio/
• Book: Storyworthy by Mathew Dicks: https://matthewdicks.com/storyworthy/
• Bootstrapped Entrepreneur: Arvid Kahl

🔗 Connect with Simon:

Twitter: https://twitter.com/SimonHoiberg
YouTube: https://www.youtube.com/c/SimonHoiberg
LinkedIn: https://www.linkedin.com/in/simonhoiberg/
Instagram: https://www.instagram.com/simonhoiberg/
FeedHive: https://feedhive.io/

Considering running webinars for your business but they’re a complete mystery to you? How often should you host them? How do you keep your audience engaged?

Moreover, how do you make people actually convert using webinars?

In this episode, Omar Zenhom, co-founder and CEO of WebinarNinja talks to us about everything webinars.

We understand why we should conduct webinars, and how to do it in a successful way. We also gather some tips on making them engaging, and increase the chances of people converting to customers at the end.

Omar also shares his story of starting WebinarNinja and his views on hiring extremely efficient people.

📚 Resources Mentioned:

• Book: Shoe Dog by Phil Knight
• Podcast: The $100 MBA Show: https://100mba.net/show/

🔗 Connect with Omar:

🐦 Twitter: https://twitter.com/TheOmarZenhom
🖥 Website: https://omarzenhom.com/

Trying to get customer feedback but getting nowhere? Having trouble prioritising feature requests while building your app? Want to change your pricing but scared of what will happen?

In this episode, Sarah Hum from Canny shares everything she knows about gathering product feedback and feature requests from 5 years of building a tool that does exactly this.

She also talks about how they prioritize requests and decide what to work on, while keeping the team happy. Finally, she also talks about challenges in managing a team as a first time founder, and her being a Twitch streamer ✨

📚 Resources Mentioned:

• Podcast: The Hidden Brain https://www.npr.org/series/423302056/hidden-brain

🔗 Connect with Sarah:

📹 Twitch: https://www.twitch.tv/xhumming

🐦 Twitter: https://twitter.com/sarahhum

🖥 Website: https://canny.io/

Running ads but not really satisfied with how profitable they are? Are there secrets to running ads more profitably? In this episode, Chris from WebMechanix shares his unique method to run ads that are optimised for revenue, by gathering the right kinds of pre- and post-click signals. We also learn how he got his first clients while waiting tables. Finally, he shares his thoughts on TikTok B2B ads and gives Guillaume a $10M idea to grow lemlist.

📚 Resources Mentioned:

• Book: Think and Grow Rich by Napoleon Hill
• Book: The Psychology of Money by Morgan Housel
• Book: $100M Offers by Alex Hormozi
• Newsletter: The Daily Rip https://stocktwits.com/c/newsletters/the-daily-rip/

🔗 Connect with Chris:

🖥 LinkedIn: https://www.linkedin.com/in/chrismechanic/
🖥 Website: https://www.webmechanix.com/

Is collaborating with influencers an effective strategy for your business? How you can find Influencers to collaborate with? What is sponsored content? In this episode, I talk to David Tintner about collaborating with influencers, creating sponsored content, and how it can help you grow your company. David is the CEO of ThoughtLeaders, an influencer marketplace for creators and brands, a company that he bootstrapped to $8M+ in 2021.

Is transparency the key to a successful business? How can you grow through content and SEO? How do you create value by offering a paid alternative to Google Analytics? In this episode, I talk to Marko Saric, co-founder of Plausible, a privacy-friendly alternative to Google Analytics. Started in 2018, the company crossed $850,000 ARR bootstrapped and is now used by almost 40k websites.