ChooseFI Logo

Rebel Entrepreneur Season 2

Welcome to Season 2 of the Rebel Entrepreneur!


Rebel Entrepreneur Coaching Series: It’s Not Linear

You’ve launched your business. You have put the product or service out for sale, you’ve launched the YouTube channel, and nothing has happened! After weeks and then months of work you are awaiting the results, but nothing has happened. Progress in a business is not linear. If you aren’t ecstatic with your business results yet then this is the episode you need to hear. Join Andrew and Alan as they talk progress, promotion, and individual focus.

Rebel Colombia

Dani, and Alfredo, the team of Entrepreneurs launching the Rebel Business School in Colombia. Together, we talk about how to start a business, whether entrepreneurship is the same the world over, and Alan’s bad sense of humor!

Bedroom Businesses

possible? Has anyone actually done that? Building a business is a long journey with ups and down, but is the dream really possible? In this episode meet someone who has done exactly that and find out what they think made the difference on their journey!

Rebel Entrepreneur Coaching Series: The Guide to Affiliate Links

The ultimate guide to getting started is with affiliate links. The idea is that you promote other people’s products (such as the ones on Amazon Associate’s Program) on your blog, Instagram, or YouTube Channel, and get paid a commission every time something sells! Is it really as easy as adding a link to your post? Or is there more science to it? After 6 months of trying and failing to earn affiliate income, Andrew has asked for help and Andrew McDonald from TechteamGB is here to support!

How to Make Your Business Famous

How do you get your business covered by the media in the newspapers, radio, and magazines? In this episode, Jon Card of Full Story media gives us practical tips to start our journey into the world of media and journalists. Jon Card writes regularly for The Guardian, The Times, The Daily Telegraph, and is the author of How to Make Your Company Famous.

Rebel Entrepreneur Coaching Series: Advanced YouTube

Let’s get geeky. There is so much more to being a YouTuber than just putting out a new video each week. In this episode we dive into the details of YouTube with two of the best. Strap in, get a pen and paper, and get ready to take notes as Matt Estlea and Rob Harvey give us the most value we have ever had in an hour long episode. We are going to break down YouTube analytics, stats, promotion, thumbnails, and every other detail you need to become a YouTube sensation! The fun thing is that the same principles apply to your business too!

Just Start: A Rebel Story

The power to make things happen come from starting. Nothing happens until you start! Join Alan as he meets Alayna from the Rebel Business School event in Charleston and finds out about her journey into entrepreneurship, her business, and what she has learned along the way. For more you can find Alayna at

The Monthly Review (Bonus Episode!)

Do you take time out of your day to review your progress? To think about how it is going, what you have done, and if it were to continue like this are you happy with the destination? One of the most important practices you can implement on a monthly basis is a review of your business/life. Doing this one thing will change the direction of your life over the long term. Thinking about your progress, your current state, and what you want to do to improve on a regular basis (if implemented) can change your future! Listen to this short special episode from Alan on how to review your business!

Rebel Entrepreneur Coaching Series: How to Get Sponsors

The difference between a successful entrepreneur and someone who talks about entrepreneurship but never does anything, is the amount of things you try. In this episode, Alan and Andrew talk about energy, making things happen, and getting things in the diary. Andrew has made some progress on sponsors and is starting to earn money from his YouTube channel, but he feels stuck with where to go next! Discover what is stopping you from getting to the next level alongside Andrew and Alan.

Pricing With Tania Valentin

How do you price your product or service? What do you charge? This can be one of the toughest decisions you will face as an entrepreneur, and one that entrepreneurs invariably get wrong and under price. Join Alan in the first half of the episode as he gives you tips and ideas on how to price, and then in the second half meet Tania who is in need of pricing advice and coaching. Let’s get you priced and selling!

Rebel Entrepreneur Coaching Series: The Life of a Content Creator

The life of a content creator can be a tough one! Whether you have a YouTube channel, a podcast, a blog, or even a business that puts stuff out on social media, it can be challenging! You have to create no matter how you feel. If you are a professional, you don’t just get to hide. You have to show up and make it happen. In this episode, we explore the life of a content creator, Matt and Rob’s biggest mistake, and Alan’s new saying “Do stuff!”

Writing Proposals That Convert

There is an art to writing proposals that convert to sales. As you build your business and work to get more clients, you are going to be asked to write proposals. Whether it is through Fiverr, Upwork, People Per Hour, or in real life, you are going to have to develop the skills to create proposals that convert to sales, dollars, or pounds in your pocket. Patrick has just become self-employed and is trying to win business, and in this episode Alan goes through the major elements of a proposal and when to send them.

Rebel Entrepreneur Coaching Series: Happiness First

This is going to sound daft, silly, and strange. Focusing on happiness is the route to success. Not the other way round! People think that if they get promoted, earn more money, and build a business that it will lead to happiness. When I have done “X” I will be happy, but that just isn’t true. Working on your happiness, learning to be happy on the journey, and having fun are actually the long term sustainable routes to success. This episode is about happiness first and so much more!

Top 10 Rebel Lessons and Episodes With Jessica Yox and Travis Howser

After 95 episodes of the show, where do you even start with the Rebel Entrepreneur? In this episode, we are joined by two of our listeners that have listened to every episode of the show so far; Jessica Yox and Travis Howser. They share with us the episodes that have had the biggest impact on them and what they learned. This is going to be a very valuable episode with some of the biggest Rebel lessons funneled into it. Strap in for the top 10 Rebel Countdown!

Rebel Entrepreneur Coaching Series: The First $100

Building a business is a journey. Sometimes it’s a long journey! But when you start to see the fruits of that labor roll in, there is no feeling like it! Andrew shares with us his first earnings on his YouTube channel, plus we discuss CPM payments, A/B testing, and creating powerful content. Your business doesn’t have to be perfect when you launch it, you just need to keep improving it each week!

You will be rejected! With Travis Howser

When you first start your business and launch, you are going to be working towards making sales. You will be rejected, people will say no, and you will be tested. If it was easy, everyone would be doing it! In this episode, we meet Travis Howser from the “Raising Golfers” podcast and hear all about his journey from losing his job during the pandemic, to launching his own business on the other side!

Rebel Entrepreneur Coaching Series: Type A Balance: PUSH PUSH PUSH

Gary Vaynerchuk is all about the hustle. We are told by so many sources to push, push, push. Hustle, hustle, hustle. If you are already a type A personality, is this the advice to follow? Do you need balance between your business, job, and family? Does Balance exist and should it be sought after? In this episode Alan and Andrew start with A/B testing, wind there way through giving tough feedback, and eventually get to finding balance for your side-hustle. Even the term has hustle in it!

Teaching Entrepreneurship with Jessica Yox

Are entrepreneurs born or created? If you believe they are created then how do you teach entrepreneurship? What’s the best way to learn business, entrepreneurship, and the startup mindset? In this episode Jessica Yox, Associate Professor of Entrepreneurship from Cleveland State University, joins us to talk about running entrepreneurial classes, what the goal of those classes should be, and how we can all learn entrepreneurship. This episode is going to open your eyes to the best way to learn how to become an entrepreneur.

The $2 Million Glamping Experiment with Will Convery & Jessica Yox

The right way to start a business is with a business plan and a loan, right? Meet Will who was on the verge of borrowing $2 million to launch his glamping business before he restructured to run a mini-experiment and test the idea in a different way. Before you launch your business, consider what you are actually building and how much risk you are willing to take on!

Rebel Entrepreneur Coaching Series: Marketing: Test and Measure

How do you know if your marketing is working or not? There is only one way! Measure the success through sales, views, subscribers, and money earned. Marketing is a constant state of testing and measuring to find out what is working, refining it, and testing it again. In this episode Alan and Andrew review what he has tested since the last episode and what he is going to do next.

Cold Sales Email with Eric Finnigan

Have you ever sat down and tried to compose a cold introduction email to someone you want to sell to or meet? Did it work? Did you get a response? In this episode Eric Finnigan is back on the Rebel Entrepreneur Podcast unpacking how to create new opportunities out of thin air through cold email. If you need to generate new business then get out your laptop and start composing as you listen!

Rebel Entrepreneur Coaching Series: Developing a YouTube Channel

What is the difference that makes the difference in the content business? How do you stand out amongst all the other blogs, YouTube channels, and podcasts? In this episode, Matt and Rob from coach Andrew in developing his YouTube channel and building his online presence through quality content.

Start by Trading

Start selling. Can you create wealth out of nothing? Can you find something on Facebook market place and sell it? Can you find something lying around you can re-sell? In this episode, our podcast editor Andrew gets coached by Stephen to build his side-hustle. Learn more about how to find deals, get prices, and create profit margins.

Get The Money First

When you are launching your business, you need everything ready to launch don’t you? Everything has to be perfect, website has to be created, business cards need to be printed, and your trademark needs to be in place? In this episode, we meet Stephen who has built an incredibly successful business finding value where others don’t always see it. Get the money first baby!

Rebel Entrepreneur Coaching Series: Coaching Series Collide

Coaching Series Collide! In this special episode of the Rebel Entrepreneur Coaching Series we have Christina from Season 1, Jaymie from Season 2, and the star of Season 3, Andrew, who you haven’t even met yet on the coaching series. Find out what it is like to be coached by Alan, what each person learned, and also get a huge number of tips, ideas, and tricks that you can apply to your business right now!

Starting a YouTube Channel from Scratch with Andrew Alinda

meets Andrew Alinda who started his YouTube channel (Cali to the Crowd) 18 months ago. We find out what it takes to get going, how long it takes to see income from YouTube ads, and Andrew’s guide to you getting going on your own channel. Let’s start creating content!

Rebel Entrepreneur Coaching Series: The Imposter

Spend as much time working on your confidence as you do working on your business. It is amazing how much time we as human beings spend doubting ourselves, beating ourselves up, and worrying about our performance. If we just took all that time and invested it in creating, building, and having fun, how much better would life be? In Jaymie’s final coaching episode, she and Alan discuss imposter syndrome, dealing with doubt, and creating confidence.

Sales: Keep the faith with Patrick Venn

If you don’t sell you don’t have any customers. It is as simple as that. What isn’t simple is how to sell, market and find those customers. Patrick left a high paying corporate sales and sponsorship job to build his own business. In this episode Alan and Patrick explore his journey into entrepreneurship and what he has learnt about sales during that first year. Be prepared for an episode full of sales tops, tools and ideas.

Rebel Entrepreneur Coaching Series: You’ve sold it, now you have to deliver it!

You’ve sold it now you have to deliver it. After getting her Kickstarter campaign funded Jaymie is now deep into the delivery phase of her kick starter. Sometimes life gets in the way. Is Jaymie enjoying creating the comic book? Is turning your hobby into a job a good idea? How do you manage getting the work done and a full time job? Sometimes following through on the promises you have made is the hardest part of any project!

“To sell or not to sell?” That is the question. With Jaymie Dylan

Sales is a divisive word. Some people think sales is pushy, sleazy, aggressive, and a bad thing; in fact a large percentage of the population believe this! For some of us we have realized that sales is a force for change, sales is a force for good, sales is something that we need to make happen to build a business, earn money and create a better world. In this episode Jaymie Dylan from the coaching episodes does a podcast takeover and grills Alan about sales and business. The tables have been turned; Alan is in the hot seat now!

Rebel Entrepreneur Coaching Series: Results, Results, Results

You can’t control the results but you can control your daily activities. After 12 episodes of focusing on the daily marketing activities, sales, and making progress, Jaymie and Alan review the results of the Kick Starter Campaign. Avoid the boom bust cycle of small business and carry on marketing even though you are focused on production.

The Aftermath of Action With Elliott Lester

Elliott Lester directed Aftermath starring Arnold Schwarzenegger, he has collaborated with HBO, Brad Pitt, and Plan B, and is working on a movie with Peter Dinklage. But how did it all start? How do you get going? How do you end up making money doing something you love in one of the most incredible industries in the world. For years Alan has been intrigued by the difference between someone who makes things happen and someone who talks about things happening and in this episode he gets to ask all his questions! This is a must-tune-in episode!

Rebel Entrepreneur Coaching Series: Market, Market, Market

If you don’t market and promote your business you aren’t going to get sales! In this episode Jaymie and Alan discuss the overwhelm that can come from marketing, how to choose marketing ideas, and the daily actions it takes to build the business of your dreams.

10 Ways to Drive Traffic to Your Website

You’ve built your website. WOOHOO! Celebrate. Then what? No-one is visiting it? I am afraid that “If you build it, they will come” is one of Hollywood’s biggest lies. If you built it NO ONE will come until you promote it, share it, get it on google, and shout about it to the world. What are you doing to get people to visit your website, see your product or service, and take notice of your offer? In this episode Henry Nicholson, COO of Rebel Business School, and Alan give you 10 ideas of how to drive traffic to your website and increase visibility.

Rebel Entrepreneur Coaching Series: Stretching Past Your Goals

So you’ve set some goals, you hit them, and you’ve failed to celebrate! What next? In this episode Jaymie and Alan unpack where the Kick Starter project goes next after hitting its goals. We explore stretch goals, the best time to make a sale, and how to engage your audience.

The Marketing Mini-Experiment

Have you ever thought about hiring someone to help you with your marketing? Alan has been wondering for some time whether it is worth hiring someone from People per Hour, Upwork, or Fiverr to help with your marketing. In this Episode Patrick (Rebel Podcast Manager) and Alan test out four contractors to see if they can actually make a difference. Test and measure baby!

Rebel Entrepreneur Coaching Series: The Big Launch and the Results

You have created the product, you have put it out there for sale, and now you are waiting for the results! Will anyone buy? Will you get customers? This week we find out the results for Jaymie’s first 6 days of her Kickstarter campaign and what has happened. You have got to listen to this one for the results and the surprising lessons from the launch.

The Beginners Guide to SEO With Henry Nicholson

92% of all internet searches happen on Google. Getting to the top of the google rankings for what your customers are searching for can be an incredible boost to your business. But is it even possible to do it? Should we be investing our valuable entrepreneurial energy and time into SEO and climbing the rankings, or should we just be paying for it as Ryan suggested in the last episode? In this episode Henry unpacks what he has learned working as a full time web developer and then on SEO within Rebel Business School for the last 8 years. Let’s get practical with SEO.

Rebel Entrepreneur Coaching Series: Promote, Promote, Promote

If you build it they will come! The movie Field of Dreams and Kevin Costner convinced us that all we have to do is build it. They forgot to add the small print which is “NO ONE will come unless you promote it! This episode is all about promotion, marketing, and getting your message out there.

Is SEO Dead? With Ryan Stubblefield

Does search engine optimization still work? Is hoping to go viral a real strategy? Aren’t paid adverts only for big businesses? You know how much Alan hates spending money on building businesses, but that doesn’t mean we shouldn’t learn about paid advertising, its strengths and weaknesses, and make a more informed decision. In this episode Ryan Stubblefield, a paid advertising expert, takes you through all he has learned from spending on advertising!

Rebel Entrepreneur Coaching Series: Self-Doubt before Launch

You are just about to launch your product, your service, your business, but have you got the price right? Is the page perfect? Are you ready? Every entrepreneur goes through the period of self-doubt before launch. Expect it, embrace it, and overcome it! Join Jaymie and Alan as they explore confidence, launching, and promotion!

Ten Ways To Market Your Business For Free! with Simon Paine

You’ve started your business but how do you get customers? Do you need to spend money on adverts? Facebook marketing? In this episode, Simon and Alan share their 10 favorite free ways to market your business and find new customers. Get a pen and paper, make a list, and start testing them now!

Rebel Entrepreneur Coaching Series: Kickstarter Page Review

The landing Page. You have got your product, you are ready to go, but before you go promoting it everywhere on social media you need a landing page. Where is all that traffic going to arrive, what will they see, and what are they going to buy.? Listen along as Alan and Jaymie review the Kickstarter landing page, the levels, and the pricing of the Mandi9 Comic Book.

Targeting Your Customer! with Jeremy Gilbertson

What do you think when I say the words, “Niche marketing” to you? Every entrepreneur fights the idea of niche marketing and finding a clearly defined market. There is a fear there of missing out on sales, and you may find yourself saying, “What do you mean I need to niche? Can’t I just sell to ANYONE?” In this episode KC and Alan work with Jeremy who is launching a new business to uncover his target market and get direction on his marketing.

Rebel Entrepreneur Coaching Series: Getting Things Done

When you launch a project there is so much to do that it can be overwhelming. How do you know where to start? How do you choose what to focus on? How do you make sure you make progress towards your goals every single day? Alan and Digital Artist Jaymie explore productivity and getting things done.

The Mysterious World of Marketing

You’ve launched your business and now you need more customers! You’ve been going for a few years and you need more customers. No matter what stage of business you are in, marketing is the perennial problem that needs tackling. In this episode KC and Alan work to break down the mysterious world of marketing to make it practical and applicable to your business now.

Rebel Entrepreneur Coaching Series: Dealing With the Critics

One of the biggest challenges you will face on the entrepreneurial journey is doubt, imposter syndrome, and lack of confidence. These things come up from our past and try and “protect” us from getting rejected by stopping us from ever trying! We have to deal with the doubt and negative spirals to help us make progress. Join us as Jaymie and Alan work through doubt!