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 🔗 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/