Bootstrapped Stories

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

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

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

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

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

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

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

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

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

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

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

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 ⚡️

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

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.

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 ✨

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.

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.

How can you reduce churn for your SaaS? What are the good tactics to use and the ones to avoid? How can you create the best cancellation process? Find everything you need to know on churn from Baird Hall, a successful entrepreneur who scaled multiple bootstrapped SaaS businesses like Wavve, Zubtitle, and Churnkey ($300K+ in MRR)

How reviews can help your business grow? What's the best way to ask for customer reviews? In this episode, I talk to Damon Chen, CEO, and founder of Testimonial ($200k ARR. bootstrapped), a tool that collects video testimonials on how important customer reviews are for your business.

How to define your company culture to attract the best talents? How do you hire people in 10+ different countries? Should you outsource some of your departments like customer support? Find out all the best hiring tips from Bridget Harris, the CEO and co-founder of YouCanBook.me - an online scheduling tool that she bootstrapped to $5.5M ARR.

Pavel bootstrapped Merge, a design agency based in Ukraine, to $1,6M ARR in 3.5 years. How did he manage to have a 15% growth during the war? What are the strategies that kept his business alive? How can you handle huge crises affecting your company? All the answers in the episode.

Wanna launch your product on Product Hunt and get maximum exposure? What do you have to prepare, what are the dos and don'ts to have a successful launch? Find out all the answers and more in today's episode with Marie Martens, the co-founder of Tally, a SaaS tool that helps you create forms online - $120.000 ARR in less than a year, 30k users.

Andrew Gazdecki is the CEO of MicroAcquire - a company that helped 500+ startups get acquired and has facilitated $300m+ in closed deals. In this episode, we're talking about everything you need to know about the process of selling a business (when it's the right time, what are the most common mistakes to avoid, what you should take into account when selling your company, and more.)

Why do all successful founders build an audience before actually building a product? It's that the secret key to long-run profitability? Where to start? What's the best way to build an audience from nothing? Find out the answers in the episode with Arvid Kahl - entrepreneur, founder of FeedbackPanda, author of "Zero to Sold", and "The Embedded Entrepreneur"

Gathering feedback from your potential customers and users helps you improve your product and accelerate your growth. But what's the best way to interview your users? What are the best questions to ask at every stage of the business? Find out the answers in the episode with Rob Fitzpatrick, serial entrepreneur and author of "The Mom Test".

Laura Roeder bootstrapped MeetEdgar to $4M+ ARR to then sell the company and start a new project, Paperbell. How did she manage to reach $1M ARR in less than one year? Why sell a profitable company to start a new one? Best tips for managing social media for your startup? All the answers in the episode!

How do you build and keep a strong company culture when you have 210 remote full-time employees? Why do you need to have a validation period for every new hire? In this episode, I'm talking to Kean about how they got to $83M in ARR in 11 years and what's their strategy for hiring the right people for the business.

Kyle Rack (CEO and Co-founder of Proposify) decided to go from bootstrapping to fundraising to buy back the shares from investors. How did they find their product-market fit? Why does Kyle think that the first employees might not be the ones who can grow the business in the long run? What's his management framework, and how does he set up team OKRs? Find out all his valuable tips in the episode.

$8M in ARR, no sales team, and 5 co-founders. That's the story of Surfer. In today's episode, I talk to Lucjan, Co-founder, and CEO, about how they started locally and expanded globally, with 60% of their customers based in the US. The Bootstrapped Stories Podcast crossed 2,800 plays.

Chris is the co-founder of Snappa. They crossed $1M+ in ARR with a team of 7. In this episode, we talked about how he quit his job to launch the business, what strategies brought them 100K+ users, and more. The Bootstrapped Stories Podcast crossed 3,300 plays.

Solo founder, Saravana Kuma brought Kovai.co to $10M in ARR in 10 years. In this episode, we talk about how blogging helped him get his first customers, how he builds strong company culture, and manages to run multi projects with totally different audiences. The Bootstrapped Stories Podcast crossed 2,800 plays.

Maxwell is the founder of Megaphone Marketing and Silvi. In this episode, we talk about the strategies that got them to $20M in ARR, bootstrapped; how he succeeds in managing 2 businesses at the same time, and what's his secret sauce for hiring top talents for his team. The episode is also available on Youtube, if you wanna watch it. https://youtu.be/eo1D666S-ow

Nathalie Lussier went from selling online courses to building a SaaS, AccessAlly. She and her team of 8 people crossed $1M in ARR. How do they succeed in a crowded market? What are their strategies to find the perfect customer and build the perfect product? Listen to the episode to see how you can get to $1M in ARR, applying Nathalie's learnings

Seller.Tools is a team of 25 people and $2M in ARR. How creating a Facebook group and publishing on LinkedIn has helped them grow? Why do they offer features for free? Listen to the episode to find all answers.

Rob Walling has switched from being a bootstrapped SaaS founder to building the TinySeed, the first accelerator designed for SaaS bootstrappers founders. In this episode, we'll talk about what it takes to build and sell 2 multi-million dollar businesses vs raising $40M. The episode is also available on Youtube.

$30M in ARR, a team spread in 28 cities, and a strong audience worldwide. In this podcast, we talk about Nathan's successful keys in growing ConvertKit, his ups and downs as a solo founder, and get valuable insight into his learnings as a bootstrapped entrepreneur. Follow Nathan https://nathanbarry.com/ https://twitter.com/nathanbarry https://www.linkedin.com/in/nathanbarry/ Follow ConvertKit https://convertkit.com/ https://twitter.com/ConvertKit https://www.linkedin.com/company/convertkit/ Follow Guillaume https://www.youtube.com/c/GuillaumeMoubeche https://www.linkedin.com/in/-g-/ https://twitter.com/GuillaumeMbh https://www.instagram.com/guillaume_moubeche/

Vivek is the founder and CEO at Question Pro. They crossed $28M in ARR with a team of 200 people. A few years ago, the business was about to fail, and Vivek was forced to rethink the entire strategy of Question Pro. In this episode, we're talking about what helped them grow and why he decided to sign a separation agreement with his co-founder back in the day. Follow Vivek https://www.linkedin.com/in/vivekbhaskaran/ Question Pro https://www.questionpro.com Guillaume https://www.youtube.com/c/GuillaumeMoubeche https://www.linkedin.com/in/-g-/ https://twitter.com/GuillaumeMbh https://www.instagram.com/guillaume_moubeche/

Jackie, CEO of Accelity Marketing, has signed more than a million dollars in contracts from leads that come from LinkedIn where she has 89K+ connections. In this episode, we'll find out her strategies for customer acquisition and lead gen, and everything that worked for her 7 figures bootstrapped business. Follow Jackie https://www.linkedin.com/in/thejackiehermes/ https://www.jackiehermes.com/podcast Accelity Marketing https://accelitymarketing.com/ Guillaume https://www.youtube.com/c/GuillaumeMoubeche https://www.linkedin.com/in/-g-/ https://twitter.com/GuillaumeMbh https://www.instagram.com/guillaume_moubeche/

Ahrefs went from $0 to $100M ARR in 10 years, bootstrapped. 65%+ growth year-over-year and tons of unconventional strategies to build their SaaS. I talked to Tim (CMO) about how they got here, why they have no tracking pixel on their website, why they don't do any testing and more. All the answers in this second episode of the Bootstrapped Stories. Enjoy!

Pretty unusual for a SaaS, right? But that's one of the unique growth strategies that helped Flodesk reach $15M in ARR in just 3 years, being bootstrapped. In this episode, Martha Bitar (co-founder and CEO) shares her learnings on what helped them grow so fast. We'll also talk about the challenges that came with such unexpected growth, as well as her hard moments. We finish up the episode with a discussion on mental adjustment and how important it is to realize that your role is NOT to be everything for everyone. If you wanna watch the interview, check out the episode on Youtube: https://youtu.be/3ZDd07nhDgY Join the Bootstrapped Family: https://lemlist.typeform.com/bootstrappedfam Martha Bitar https://www.linkedin.com/in/marthabitar/ https://www.instagram.com/marthabitar/?hl=en Flodesk https://www.instagram.com/flodesk/?hl=en https://www.linkedin.com/company/flodesk/ https://twitter.com/flodeskinc https://flodesk.com/ Guillaume https://www.youtube.com/c/GuillaumeMoubeche https://www.linkedin.com/in/-g-/ https://twitter.com/GuillaumeMbh https://www.instagram.com/guillaume_moubeche/