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© Guillaume Moubeche
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Welcome to Bootstrapped Stories, the podcast where founders, marketers, and thoughtful leaders share the most actionable tips on building a successful business.
44 Episodes
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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
How do most people get content marketing wrong? How can you differentiate yourself and do it in the right way?
Rand Fishkin from Sparktoro talks to us about his unique mindset of publishing content online, what he thinks about the accuracy of attribution, and what he thinks of before deciding a distribution strategy for a piece of content.
We also talk about his thoughts on fundraising vs. bootstrapping, why the press doesn’t cover bootstrapped businesses, and what he thinks of Elon Musk buying Twitter.
⏱ What you’ll find and when:
00:00 Intro
02:41 Transitioning from Moz to Sparktoro
05:07 Thoughts on bootstrapping vs. VC funding
10:06 Why the press doesn’t talk about bootstrapped businesses
13:23 Sparktoro’s unique funding model
24:46 What Sparktoro does – finding more media channels
30:08 Thoughts on attribution
38:18 Rand’s unique content mindset
43:49 Content distribution the right way
51:03 Choosing the right titles for your content pieces
53:27 Thoughts on Elon Musk acquiring Twitter
57:34 Flash questions
🔗 Connect with Rand:
Twitter: https://twitter.com/randfish
LinkedIn: https://www.linkedin.com/in/randfishkin/
Sparktoro: https://sparktoro.com/blog/
As a four time entrepreneur over more than 15 years, what are the biggest lessons learnt in management, levelling up as a founder and coming up with business ideas?
Jason Cohen from WP Engine talks to us about why he decided to raise funds after bootstrapping successfully in the past, and how he comes up with business ideas.
We also talk about evaluating your managers, how managing your executive team is very different from managing other members of the team, how the role of a founder evolves over the years and the different ways that you can level up as one.
⏱ What you’ll find and when:
00:00 Intro
07:33 Reasons to raise funds after being a successful bootstrapper
12:50 Jason’s thoughts on financial reporting
23:45 The best way to evaluate your managers
30:05 Acquisitions: impact, challenges, successes
38:18 Coming up with $1B business ideas
44:36 How the role as a founder evolves over time
51:25 Levelling up as a founder
57:52 How to successfully manage an executive team
69:33 Where you can find Jason
🔗 Connect with Jason:
Twitter: https://twitter.com/asmartbear
Blog: https://blog.asmartbear.com/
How do you grow through word of mouth? How can you get customers to recommend you to others? Can you get enterprise and mid-market clients through this?
Muhammad Younas from vFairs talks to us about how his company grew to $30M through word of mouth, even during the pandemic, and being fully remote from day 1.
We talk about the importance of customer satisfaction, the similarities between online events and weddings, and how you can structure your support team to make sure that customers are happy.
We also speak about managing a 260+ person company while being fully remote, and the biggest challenges he faced while building the company.
⏱ What you’ll find and when:
00:00 Intro
01:19 Intro to vFairs and key stats
03:51 How did the pandemic impact growth?
05:44 Why they decided to stay bootstrapped
08:30 Key metrics to understand the health of the business
12:43 How to get more word of mouth
14:06 Getting their first mid market and enterprise clients
18:34 How a support team is structured for success
24:27 Sales cycle differences between mid market and enterprise
29:25 IPO plans 31:52 Managing a fully remote company
40:12 Biggest challenges faced while building vFairs
43:11 Flash questions
🔗 Connect with Muhammad:
LinkedIn: https://www.linkedin.com/in/younas/
vFairs: https://www.vfairs.com/
How do you build a strong culture among a team that’s fully remote? How do you make sure people are motivated and goal-driven? What do you need to look for when hiring a coach for your team? What is non-violent communication and why is it important?
Nicolas Vandenberghe from Chili Piper is a serial entrepreneur, and he’s been there and done that. In this episode, we discuss all of the above, and also talk about their acquisition channels, raising money as a bootstrapped founder, and challenges faced by solo entrepreneurs.
⏱ What you’ll find and when:
00:00 Intro
02:38 Raising money as a bootstrapped founder
09:51 How do you decide the right moment to raise money?
13:26 The secrets to building a strong culture in the sales team
21:49 Hiring coaches to grow your team stronger
26:49 Acquisition channels to transition into something bigger
30:54 Advice on customer success and account management
32:08 Chili Piper’s ideal customers
36:36 Challenges towards $100M ARR
41:09 Difficulties and challenges faced as an entrepreneur
47:09 What it’s like to work with your wife
49:02 Some golden advice for solo founders
51:26 Flash questions
🔗 Connect with Nicolas:
LinkedIn: https://www.linkedin.com/in/nvandenberghe/
Chili Piper: https://www.chilipiper.com/
What happens when you realise you need to change your pace, and want to hire someone else to run your company? Can you really hire someone to run the company as well as you can? What do you need to have put in place to be able to do that?
And then, what happens when that person wants to leave and you need to either find someone else or do it yourself?
Noah Kagan, cofounder of AppSumo, a daily deal website for software, has been there and done that. In this episode, we talk all about it.
⏱ What you’ll find and when:
00:00 Intro
02:34 The story of founding AppSumo
07:16 AppSumo’s hiring philosophy
08:47 Hitting a business plateau and taking a step back
11:27 Hiring a CEO to run the company
20:39 Trying to hire a CEO for the second time
28:04 What makes AppSumo excited for the future
36:07 The things they did to truly level up
🔗 Connect with Noah:
LinkedIn: https://www.linkedin.com/in/noahkagan/
AppSumo: https://appsumo.com/
Twitter: https://twitter.com/noahkagan
What are the challenges of acquiring other companies? What has to change as your company grows from a startup into a scaleup? What are the mistakes to avoid?
Ross Andrew Paquette is the CEO and founder of Maropost, a company that grew from a 20 person lifestyle business to a 300+ person business doing $60M in ARR, acquiring 2 other companies in the process.
In this episode, we get all the learnings and challenges that Ross faced during this time, and the things he’d do differently if he could go back.
⏱ What you’ll find and when:
00:00 Intro
03:10 The biggest challenges going from 20 to 300 people
08:26 The things that worked well for hiring
12:38 Story of selling a quarter of the business and then buying it back
16:33 Acquiring 2 companies: challenges and learnings
25:30 Organising a 300-person secondary funding round
28:29 Maropost’s customer acquisition strategy
38:16 Transitioning from being an operational CEO to hiring people
44:24 Flash questions
🔗 Connect with Ross:
LinkedIn: https://www.linkedin.com/in/rossandrew1/
Maropost: https://www.maropost.com/
Instagram: https://www.instagram.com/rossandrew/
Is a good user onboarding really that important for your SaaS product? What are the most common mistakes to avoid in creating one?
In this episode, we speak with Esben Friis-Jensen from Userflow, a no-code user onboarding builder for product-led tools. We learn about the importance of onboardings, the mistakes most SaaS tools make when designing one, and what goes into creating a good onboarding.
We also get what it means to find your “Aha!” moment, and how that can greatly help with designing your onboarding for success.
⏱ What you’ll find and when:
00:00 Intro
04:34 The Userflow team and deciding equity split between founders
10:57 The Userflow growth strategy
13:35 The most common user-onboarding mistakes companies make
16:29 How to design an effective onboarding
22:46 Implementing data directly into your product
25:33 Product-led growth for a $600 product
31:23 Figuring out your Aha! moment 34:16 Bootstrapping vs. VC
37:50 Flash questions
🔗 Connect with Esben:
LinkedIn: https://www.linkedin.com/in/esbenfriisjensen/
Userflow: https://userflow.com/
Product-Led Stack: https://www.productledstack.com/
Can you scale your SaaS with ads? How useful are affiliate programs and how do you set one up for success? Should you offer lifetime deals for your app?
Joey Xoto shares with us everything he’s learnt while scaling Viddyoze. We talk about about affiliate deals, his thoughts on lifetime deals vs. monthly subscriptions, we learn about the different PPC sales funnels that Viddyoze uses. Joey also shares his thoughts on scaling and then cutting back on team size.
⏱ What you’ll find and when:
00:00 Intro
03:52 Scaling back on team size
13:43 Acquisition through their affiliate program
26:26 Thoughts on lifetime deals vs. recurring offers
33:20 How to protect your brand when offering lifetime deals
36:22 Everything about sales funnels
40:43 Flash questions
🔗 Connect with Joey:
LinkedIn: https://www.linkedin.com/in/joeyxoto/
Viddyoze: https://viddyoze.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.
How can a simple side project help you to boost your main business? Why persistency is key to success as an entrepreneur? How did Flexible make its first $100,000 using Google Sheets? In this episode, I talk to Karthik Sridharan about his story as the co-founder and CEO of Flexiple. Started in 2016, Flexible is a marketplace where companies can find top freelancers to grow their business. Today, they’ve reached $3M in ARR, 100% bootstrapped.
Why are quizzes one the best way to best generate more leads? How can you start using quizzes to generate more revenue for your business? What’s the best way to design them? In this episode, you discover everything you need to know about quizzes from Josh Haynam, CEO, and co-founder of Interact, a quiz building tool that he bootstrapped to $3M ARR.
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