I'm Chris Guillebeau, author of The $100 Startup, host of Side Hustle School, AMA!

Hi, I'm Chris Guillebeau, author of The $100 startup, host of Side Hustle School, and slightly reformed juvenile delinquent. My new book The Money Tree comes out on April 7.

I was supposed to go on a 40-city tour, but now I'm touring from my couch.

I'll be here on Thursday 9th of April from 1pm Pacific time, ask me anything!

  1. 8

    The $100 Startup is one of the few books that I read from front to back more than once. What is the new book about?

    1. 2

      I’m glad it was helpful! Since you’re familiar with $100 Startup, one way to think of THE MONEY TREE is that it’s like that but in the form of a story. In other words, it’s not a how-to book with a lot of steps; it's more of an immersive narrative.

      Big picture-wise, it’s the story of becoming self-reliant through financial independence. Practically speaking, it’s about using creative thinking and application to get out of debt and reduce the impact that external factors (your boss, the economy, etc.) can have on you.

      My goal is to reach a lot of people who are struggling financially, but who might not read business books.

  2. 4

    Hey @ChrisGuillebeau! Glad you're doing an AMA (i really enjoyed mine)!

    ### Question:

    How have you built community over the years? Has your strategy(ies) changed? What has worked the best for you, especially as an author?

    1. 3

      teach me this formatting please! how you write like that? with quote lines and all

      1. 2

        That's Markdown format. This is a great resource -> https://www.markdownguide.org/

        A lot of forums and apps now allow for this format.

        1. 1

          That's really a great resource, added to bookmarks already. Thanks man ⚡️

          • I'll
          • learn
          • markdown
          1. 1

            Nice. You have a wonderful Markdown journey ahead of you. There is a lot of cool stuff to do with it.

      2. 2

        just use these:

        Separate paragraphs with blank lines.
        Italicize text by surrounding it with asterisks *.
        Make lists by starting lines with hyphens or numbers.
        Quote text by opening the paragraph with a greater-than sign > followed by a space.
        Write code by indenting 4 spaces or surrounding it with backticks `.
        URLs automatically turn into links.


        there's a small button on the right side of the input window too.

  3. 3

    What's the best practical and actionable advice/s you can give to junior developers? :)

    1. 1

      This might not work for everyone, but if possible, try to “team up” with someone who has an interesting message or product but who needs technical help.

      I mention this because it’s how I started with @nickyhajal, who I still work with today on more than half of my projects (including most of the ones that do interesting web stuff). In my very first year of blogging, he sent me a note with a suggestion: he didn’t like the pop-up email subscription form I was using … so he made a better one and offered it to me for free.

      And it really was better! This was the start of a longterm friendship and collaboration. For those who said elsewhere that they have really enjoyed WDS—well, Nicky made the app, the website, and has been part of our planning team since year one.

      I think his approach worked because he built a solution to my problem. If he just said, “Your popup sucks” or whatever, I wouldn’t have listened—not because he was necessarily wrong, but just because I was constantly hearing from a lot of people and couldn’t give attention to everything. But because he’d already thought it through and worked it out, it stood out from a lot of other messages.

  4. 3

    @ChrisGuillebeau I don’t have any questions for you. I just want to thank you.

    WDS 2017 changed my life. It was the first time I cried as an adult, the first time I embraced my vulnerable side, the place I found my first life coach, the place I first talked about all of the anxiety and pressure and fear I have inside me.

    The past few years have been an incredible journey for me. A journey of travel, existential reflection, divorce, depression, openness, friendship, connection, and so much more. The hardest few years of my life that, as the breath calms, leave me in the most grounded and positive place I’ve ever been.

    WDS was the catalyst for all of that (and also the main reason I live in Portland now).

    I’ve thought about writing to you so many different times. And I’ve never done it because I don’t have the words. I don’t know where to start. So… I still hope to write something more complete and articulate at some point, but I guess this is me starting 🤷‍♂️

    Thank you.

    1. 1

      Hey Patrick, thank you so much for your kind message. Very glad to know that the event came together with a time in your life where you were ready for positive change. 🙌🏼

      I'll share this note with the rest of the team as well—I certainly couldn't put WDS together on my own! Hope to see you again in PDX or elsewhere sometime soon.

    2. 1

      hey, I was at WDS in 2016. I know what you mean, WDS and the community I encountered there was really powerful for me, too. Noticed you're in Portland, I definitely hope to return sometime.

      1. 2

        So glad you were there too! I hope we can connect another time and place.

        1. 1

          Thanks, I have an eye on WDS 2021 so we'll see :)

  5. 3

    Hey Chris. Looking forward to reading your new book!

    I am trying to build a community for data science people to help them build their portfolio and get hired. What's your perspective on community building strategies? How would you start if you had to build a community for data science people?

    Thanks anticipated!

    1. 1

      Second this, but for short term cybersecurity pros (www.getblueteam.com). I was running a meetup before Covid, and have built a consulting firm in New York. Any idea how to reach potential customers, as well? I think that's the harder side for scooch and me to solve.

  6. 3

    Hi Chris, thanks for doing AMA.
    I'm working on a side project called Open Startup List where I curate all startups that share their metrics such as revenue and traffic in public. I'm also working on expanding this and currently interviewing those founders. Readers will have deeper insights into these startups and my website will offer more insightful content.
    I wanted to ask you, how would you grow this (as an experienced founder) and what advice would you give? :)

  7. 1

    Hello Chris,

    Happy to hear about your new book, $100 Startups is one of my fav book, you inspired a lot of people,

    After reading your book, i started OyeStartups . thanks for inspiring people like us

    and we are waiting for your new book :)

  8. 1

    When making new product (software-product) in the business area you know little about, how important you think is to have partner / test-customer to help you ? Or is one test-customer even enough ?

  9. 1

    Since you've traveled so much - what is your favorite country?

    Since you're spending so much time at home, what's your favorite room? :)

    More seriously, what was the reason for the online coffee business shift to the writing? I'm not sure I've heard the reasoning for that shift from way back when?

    1. 1

      Haha - exactly. My favorite room is probably my home office, where I spend most of my time.

      As for that timeline, I tell the online coffee business story a lot because people often ask “How did you get started?” (For those who don’t know: 20 years ago I learned to buy and sell things on Ebay when it first came out, and coffee was one of the categories I was most active in.)

      But I really only did that for a short time, maybe a year or two when I was 19 and 20. I started the blog a decade later, when I turned 30 and came back to the U.S. after living overseas for several years. In between was four years of being an aid worker in West Africa, two years of grad school, a lot of travel, and numerous small entrepreneurial activities like affiliate marketing, Google Adwords/Adsense arbitrage (back when that was a thing), and other projects.

      So it wasn’t really a strategic shift from one thing to another, more like an evolution.

  10. 1

    What are your personal long-term goals with your work, your writing, and your speaking? (By personal I mean what do you hope to accomplish for yourself, rather than what you hope to help others accomplish.)

  11. 1

    Hi Chris,
    Loved The $100 Startup!
    If you had to launch a side hustle today, what markets or niches would you aim for to stand the most chance of success?

    1. 1

      Thank you! I'm glad it was helpful.

      As for launching a side hustle today, first (and always) it depends on what the goal is. Making money in the short-term is very different from building a business—and there's nothing wrong with either approach, it's just that the best path forward requires you to know where you want to end up.

      Short-term wise...

      -Anything in the world of wellness (broadly speaking - home exercise, meditation, etc.)
      -Anything to do with remote work (broadly speaking - technological, cultural, etc.)
      -Anything to do with corporate training, esp. with businesses adjusting to remote work
      -Anything that focuses on connecting people or making them feel less isolated. Community is everything these days!

      Backup plan: go back in time three months and invest in Zoom.

      1. 1

        Awesome answer @ChrisGuillebeau, thank you! They're all spot on.

  12. 1

    How have you approached doing a book tour from your couch?

    1. 2

      Like everyone, I’ve had to rethink and regroup. Mostly, I’m trying to “show up” wherever I can and be helpful. I’ve started a new YouTube Live series where I’m teaching a short lesson and answering questions every weekday. I’m doing Instagram Live pretty much every evening, seven days a week. I’m doing several podcast interviews a day and speaking to lots of groups remotely—basically wherever people are, I’m trying to be available.

      Book tour has its challenges, but so does remote touring: on Monday I’ll be on one of the largest TV shows in Canada, which of course is an honor (or an honour, I suppose)—but the segment is at 7am Toronto time, and I’m on the west coast … so that means I need to be ready by 3:45am for a test call. The alternative would be to say no, but I try to do everything I can to support the book.

      I’m not selling anything through any of these projects, by the way. I want to promote the book, of course, but aside from that there’s no secret backend membership site or whatever. It really is about sharing ideas and trying to help people see more of what’s possible.

  13. 1

    You're amazing. I use the mental model of the $100 startup so often. I use it too often now.

    I'm launching a quick side project nearly every 3 months. Some suck. Some are profitable.

    But the profitable ones aren't getting over a few dozen dollars.

    Any advice on getting to the next level?

    The only one I spent more than $100 on failed miserably with no sales.

    Here's what I've launched recently:
    $8.99 domain expense and $50 revenue for nocodeblackfriday.com (deal site for no code apps) (Nov 2019)
    $8.99 domain expense and $30 revenue for bettersheets.co (video tutorials for google sheets) (April 2020)
    $500/ month expense + Revenue $1k a month for Influenceweekly.co (a newsletter about influencer marketing) (Launched Nov 2017)
    $7.99 domain expense plus CRM and $1,700 Revenue for Hypeletter.com (sales for newsletters) (Dec 2019)
    $3k expense and $0 sales for creatorgrowthlab.com (growth tactic analytics for influencers) (May 2019)

    1. 1

      Hey Andrew—well done on launching those projects! Most people never get that far ... or if they experience a setback, they never regroup and try again.

      I haven't gone to look at all the sites yet, but here's my "first take" based strictly on reading this.

      -Deal site: sounds like something people might visit one time if it came up in search results, then never return. It's very hard to build loyalty in coupon / deal / bargain sites.

      -Influenceweekly: are you an influencer? Do you work in an agency that does ad buys with influencers? If not, I'm not sure this is a good topic. Regardless, I also think the world of "influencer marketing" is a bit of a bubble.

      -CreatorGrowth: kind of like the last question, is this your field? Do "influencers" actually buy anything, or do they expect everything to be free?

      To be clear, I don't meant to sound skeptical about these things, and I may have got some of the comments wrong. But the point is that I'm wondering if you've really narrowed down on the convergence point that I wrote about a lot in $100 Startup: a) what you care about, and b) what others value.

      If you are missing either element, or the match isn't well aligned, it's going to be difficult.

      The good news is you seem to have no shortage of ideas. :) Keep trying stuff!

      1. 1

        Just to give you some back story: I worked in an influencer marketing agency for 3 years. In a Pricing and Analytics role. The newsletter is born out of that experience and what I see missing in the talk of "Influencer Marketing". The data. And empowering the influencers/creators who are asked their rates.

        Happy to talk about what's bubble or not. "Influencers" are far different than "Influencer Marketing". In fact that's what a lot of my work revolves around: Finding the true north of the industry, not just the hot trend.

        Maybe it's not a convergence point yet... but I'd like to help digital creators.

        A) You're right. Creators don't buy. That's why creatorgrowthlab.com failed.

        I probably should have put them in an order that made sense.

        I made Influence Weekly 2 years ago, Working well.

        Had a audience development agency for 5 years. Helped about a hundred influencers grow their audience: 2k to 5k new followers a month.

        Wanted to help more creators grow. CreatorGrowthlab: Failed because creators didn't want analysis. They wanted action.

        Decided to niche down to newsletters: Hypeletter.com

        Realized that most of us start creating new projects in Google sheets: Made BetterSheets.co

  14. 1

    Chris, hey! I was at WDS in 2016 (https://medium.com/@Jasraj0/wds-2016-the-experience-of-a-lifetime-e2a5f301095b) and have been following you for a while.

    I wanted to ask:

    1. How do you feel blogging has/hasn't changed since you started out?
    2. How do you manage your energy? I'm amazed at how you take time to respond to emails personally (thanks!), do things like WDS and all the book-tours, etc.
  15. 1

    Hi @ChisGuillebeau ,

    Your book are so very interesting to read. I read a few page of it, looking forward to buy a copy soon.

    So for my question: I have an idea right now (a travel pooling app), the idea seems appealing for some people. I don't have validate it yet on a wider target audience. I'm planning to show it off once i have the product.

    Currently, i'm starting to work on the mvp of my idea. However, i still don't think yet on how i can monetize it. Is it good for an idea to continue working on, despite of not having a plan for monetization yet?

    1. 1

      Without getting into the specifics of your idea, I don't think it's ever a good plan to move forward without a clear revenue model.

      Here I'm speaking of a project that you want to make money from. If you're just doing something because it's interesting to you, that's different.

      But since I'm assuming you want to make money from this business, my suggestion would be to either:

      a. Choose a different idea (you probably have many, right? ideas are usually the easy part), or

      b. Think a lot more about how you'll monetize this idea, because that might determine the features you need, user base to build for, etc.

      In other words I think it's a mistake to say "I'll figure out the money part later." Figure it out first!

  16. 1

    Hi Chris!

    I want to first start out and thank you for your work. Back in 2011, breaking out of the 9-5 seemed all but impossible, but the work you were doing—which I found out about through the 193 countries project and the AONC blog—had an enormous impact on both my confidence (I found it!) and game plan. I even came to a book signing in Denver in 2012, and I appreciated how you were able to spend a little one-on-one time with everyone there.

    How do you address self-doubt/anxiety when launching ambitious projects? Especially ones that, as it seemed with 193 countries, seem more than a few degrees removed from "the norm," where people might not know how to think about the problem in the first place, much less appreciate its significance or scope?

  17. 1

    Hi Chris, what are your thoughts on design sprints?

    1. 2

      I'm not super familiar with that specific model (I did some reading and it looks interesting), but in general I'm a fan of any process that allows someone to make quick progress and end up with a deliverable—whether it's a hackathon, Startup Weekend type of event, or some other process.

      Whatever helps you move forward is your friend. Whatever keeps you stuck in analysis is your enemy. "I'm doing more research" is often code language for "I know what I need to do but I'm procrastinating."

      (I say this as someone who does a lot of research...)

  18. 1

    @ChrisGuillebeau I recently purchased your book and it's amazing i'v read 50 pages so far. The teacher who love to do coding as hobby and created his tool for expense management and after that he starting selling to others and making good amount is very cool story. However, i will ask you some questions later on thank you.

  19. 1

    I guess it's my lucky day! 😁

    Hey Chris!

    I've got a $30 startup called Insteps which allows people to write instructions and how-tos step-by-step in the form of to-do lists. Think of a thing you would want your readers to do. You can tell what to do by creating actionable to-do list items. Every time a user checks off from the list, you can view the statistics that tell you what's going on.

    Do you understand? I am struggling to take off. I am still looking for customers to gather feedback to make the product effective.

    Do you have any advice in general? 🤔

  20. 1

    Hi Chris,

    I've enjoyed your books and follow your podcast. Thank you for being of such help for others getting started in this (like me).

    So for the AMA: From a business perspective, how are you dealing with the COVID-19 crisis? Are you making less emphasis on selling? Maybe focusing more on marketing and product development?


  21. 1

    How long are your books typically? Is it more breadth or depth?

    1. 1

      Typically 60,000-80,000 words, fairly standard for nonfiction. I forget the word count for THE MONEY TREE but I believe it's also in that range.

      As for breadth or depth, hmmm—I try to be as comprehensive as possible while also writing for a mainstream audience. If you're fairly experienced at starting and launching projects, some of what I write about might be a little basic for you. At the same time, I try to highlight lots of stories from all kinds of people, in the hopes that every reader will relate to someone or something.

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