Do you Need to Quit Your Job to Build a Successful Business?

Do you Need to Quit Your Job to Build a Successful Business? post image

We get a lot of emails from readers of this blog ( This week I thought I’d respond to some here. Feel free to write us if you have questions you’d like to see written about. Today’s topics include making money from writing, digital nomad documentaries, starting productized services, and remote jobs.

Hi Dan,

I had a question about the advice you give about quitting your job. Is this really the only way to move forward in building a business? I know Tim Ferriss has said that nights and weekends would suffice to building a business. I have also heard of a few people who built their business with limited time. This really pushes me away from the dream of entrepreneurship if I have to quit my job and wait 5 years because my family needs financial support from me.

Thank you for your response,


Back in the day I strongly encouraged quitting your job. But there are lots of ways to get more freedom and flexibility in your career and business without necessarily doing that. Let’s dig a little past mere possibility and start to look at what’s working for people.

One of the best places to look for the likelihood of someone achieving business success is in the nature of their current occupation.

The idea of having a ‘normal’ job, and then moonlighting in the evenings and weekends with something entrepreneurial is romantic. Making it happen is certainly within the realm of possibility, but with an unrelated career plus family obligations, you’re stacking the odds against you and putting a lot of pressure on yourself.

The good news: the first step is (relatively) simple. Begin by treating your personal finances like a business. Start looking at your financial life like a profit and loss statement (P&L) and you’re already thinking like an entrepreneur.

The second step is easier than starting a business but still challenging, with many potential upsides: improve the quality of your job (there’s a similar point to be made if we just replace ‘job’ with ‘type of people you surround yourself with daily’).

What’s lacking in your career that’s inspiring you to think about spending nights and weekends building a business? Do I think it’s possible to spend your spare time putting up a few sites and testing things on the web? Yes. Do I think that approach typically leads to entrepreneurial successes? Often, no. That’s alright though: entrepreneurship is a long journey that involves a lot of small steps. If putting up a website on the weekend provides you with more information to make your ultimate career decision then, by all means, do it. But ultimately, we’re talking about improving the quality of your main income. Why not start today?

Could you make your job more exciting?

Could you work remotely?

Could you champion projects within your company that are revenue focused? (Ie, results oriented?)

Could you get a job or a career that has strong “parlay” opportunities? This is the best bet for a “nights and weekends” outcome, and it’s demonstrated in Tommy Griffith’s interview “The Saturday Morning Side Hustle.” Yes, he built a business on nights and weekends. But it was an SEO training business. And Tommy was the head of SEO at Airbnb. That’s what I call a parlay.

Many people interested in entrepreneurship undervalue their career experience and instead look to start gimmicky businesses they read about on blogs like TMBA. If I had a nickel for every financial planner or sales professional or lawyer or accountant who’s trying to open a dropshipping store…. I’d be in the nickel biz.

Here’s a decent rule of thumb: if you’re going to start a business, start one in the industry you’ve spent years training in.

Whoever is paying you is (typically) making many times your salary by employing you. So, in a way, you’ve already positioned yourself at a nexus of value. Can you improve that value meaningfully to the company you’re in? In other words, can you put your job to work for you? If not, it might be worth seeking a career change.

If you can’t, consider apprenticing for somebody you’d like to emulate. All things being equal, I think folks would make more progress by donating their time on the weekends to an established business (provided you can work directly with the founder) rather than trying to do it on their own.

Got more money than time?

Some careers can put you in a position where you have more money than time, and so many opt to buy businesses that are already established. It’s worth pointing out that owning a business and entrepreneurship (a know-how and skillset) are very different things. You cannot consume your way to entrepreneurial know-how (buying businesses, ads, courses, etc).

Certainly you can start to learn the latter by doing the former, but typically the skill set takes years to build.

That’s why entrepreneurial jobs and apprenticeships are so powerful– you’re getting paid to learn.

Short answer: nope, you don’t need to quit. Treat your personal finances like a job. Improve the quality of your job and career. And start tinkering on the side. You won’t regret pushing yourself and learning new things (so long as you don’t spend a ton of money doing it).

Also: see “exit velocity” below.


Hello Dan,

Thanks for doing this. I know you get this a lot but here goes. If you were to start with $1000, how will you get a productized service up and running? How will you come up with an offer? How will you get that offer infront of people?


For those of you following along at home, a ‘productized service’ is a service business that’s presented like a product (why present it like a product? Speaking loosely, because services/freelance businesses tend to be the easiest to start but hardest to run. Productizing services goes some way to solving the traditional challenges with services).

Take a look at WiseMatch here at Dynamite Jobs. It’s a productized service. For a similar service, recruiters might charge many thousands of dollars or a percentage of candidate salary. On the other end of the spectrum, you could imagine WiseMatch being executed by software but being presented essentially the same way.

Productized services have many advantages for founders who lack capital and technical skills. That’s part of the reason we’ve spent a great deal of time talking about them here at TMBA– in fact, if you’re up for it, you can go on a deep dive today. I’d start with “The Rise of Productized Services,” and then listen to our most recent commentary on the topic: “You Are Not Working With Clients Anymore, You are Working With Customers.”

The archives of this blog are stuffed with ideas and case studies about the business model and those testing it. There’s even “An Episode for Those Who Need a Business Idea.” I’ve compiled a list of over 10 relevant episodes on the topic at the bottom of our ‘best of’ page.

Another concept to explore is “10 True Clients, 100 True Customers, or 1,000 True Fans.” A sweet spot for productized services that scale is to find something that companies might otherwise pay 1000’s for and find a way to deliver the same thing for 100’s. Tommy Joiner is doing this by saying, “Don’t bother hiring an experienced writer, we can do it for you.” Design Pickle says the same for design. Greenback the same for international tax accountants. WiseMatch for recruiters.

Or you could take a “10 True Clients” approach by determining a deliverable that’s worth 500 to 5000 bucks a month from 10 to 20 companies. This is the area where SWASing powerful software (delivering Software With a Service.. think implementing powerful software tools like Hubspot, Ahrefs, etc) can make a lot of sense. A lot of companies, for example, have made the investment in an expensive piece of software but the most expensive investment is in the expertise and time to implement it successfully. If you can establish yourself as an expert there, you can get started today.

Regarding positioning and offers: my approach would be whatever gets them on the phone the quickest. Too many early-stage entrepreneurs take already running businesses as a model and therefore cook up funnels and ad sequences etc to replicate that. In businesses I’ve been involved in, we’ve always started on the phone and in person. You’ll learn a lot faster and get better results.

So if I’ve only got 1,000 bucks and no business idea, I’d probably get a job with somebody who can give me more “exit velocity.”

“Exit Velocity” = The amount of professional and entrepreneurial momentum you have when quitting your job and starting a new venture. Momentum can come from a variety of sources: investment, capital, experience, anchor clients, industry knowledge and connections, etc. AKA: unfair advantage.

Exit velocity is something that is rarely talked about on the entrepreneurial web, but if you start peeling through successful case-studies you’ll see it everywhere. The #1 source of exit velocity, or what business writers sometimes call “unfair advantage”, is a highly relevant career experience (and the relationships gained therein). Getting a relevant job is much less challenging and potentially more powerful than starting a business that might be doomed to fail.


Why hasn’t there been a good documentary about Digital Nomads?

-Anon TMBA Readers

It’s true: the docos so far haven’t been compelling. Yet, I understand the drive to create them. For me, understanding that I could build wealth from anywhere on the planet was a life-changing insight and belief. And for me, personally, it meant the world.

But for others? There’s no inherent drama.

Once somebody quits their job and starts a remote business, their lives look pretty similar to regular people’s minus the office bit. It’s not particularly gripping stuff. After the first few years of, “Holy shit I’m making money from a rice paddy check out my IG PEOPLE!!!”, that fact itself isn’t enough to be interesting or dramatic. The question remains: how to you inject drama into it? What important problems are people trying to solve? For the average digital nomad or entrepreneur, they’re just trying to figure out how to eat, get paid, and have fun, which doesn’t make compelling viewing.

I do believe, however, that Digital Nomadism is ready to be the cultural background of a dramatic story. Think what The Beach did with backpackers, or what Rounders did with poker players. Seems like Kyla’s on to something here (also here’s an episode we did about good books).

Here’s another way to say it: Digital Nomading itself isn’t important. But there’s a lot of things surrounding it that are. Writers/producers are better of focusing there.


What has changed [since you wrote “Is Blogging Still a Viable Way to Start a Business.”]


Nada. If I wrote the article today, I’d change some of the example links. But I keep the old ones because it’s worth taking a look at how people’s journeys change, and that the important thing is to get started. So, to be clear: is blogging still a viable way to start a business? Hell yeah.


Hello Gents long time lover of ye… so just wanted to give you some feedback… I’ve been remote for a couple of years, starting my own company that failed, and I recently joined a company called “Respondent.”  Not quite a lifestyle type of company, there’s a dozen of us so I was talking to the head of people ops about hiring… I mentioned your job site and her feedback was that it didn’t seem like the kind of thing where she could get enterprise level people. She thought it looked for much smaller companies, just wanted to give you that feedback.

Thanks James.

True. So far we’ve found ourselves to be good at operations, marketing, and customer Service for small (<50 employees) internet businesses (not surprisingly, much like the type of companies that high flying readers of this blog are building). Our contact list is currently 15K +, and our detailed database of screened candidates of 2K of folks of varying level of experience and qualification in the above categories. But yeah, no enterprise, sales, or technology positions yet.

Thanks for all the email!

Love your prompts and question, let us know what you’d like to hear about in the comments on in our inboxes.

Happy hustling and see you next week,


PS, you don’t need to quit your job to have more freedom and flexibility. You can just get a better one at Dynamite Jobs.

Published on 01.22.19
  • I would be worried that a digital nomad doco would be along the lines of the Fyre Festival documentaries, and we don’t want that! There was a backpacker doco “a map for saturday” which just tells the story and I would say only has a following among backpackers. I think a novel is the best bet, or a fictionalised story based on ones life (like how Gregory David Roberts fictionalised his life story in Shantaram).

  • 100% on the novel being the best bet, I’ve often played around with a napkin (using Steve Pressfield’s foolscap method) about dramatic arcs that would work, if pushed I would default to a loan/investment gone wrong and somebody needing to start a business fast to pay back the money :) Looking forward to somebody doing that!

    Yeah that’s a good point so far the docos have been *barely* interesting enough for DNs themselves let alone the broader culture.

    I also will take your word and not google Fyre Festival Docos. :D

  • Matt

    For a digital nomad documentary check out “One Way Ticket” by @youjindo. I liked it.

  • Dan, thank you for the insights, now going to check the links you have inserted. Would like to hear more about buy-vs-build. I don’t have enough time (9-5 job + 2 small children) to start from scratch so buying looks to be a solution. If something on that topic was already published please share the link.

    About Dynamite Jobs. Are you interested to promote it to Russian tech crowd? Here I have one idea, pls DM/tweet me if interested.

  • This would be typical of how most of the filmmakers are approaching the topic (and many of the requests I see essentially look similar to this project). It’s okay but fails to be interesting to the broader public.

  • Hi Pavel I know we’ve brought the topic up a few times but I’m not sure we’ve ever created something dedicated to it. I’ve been speaking with a lot of small internet business investors lately, and have been cooking up a rule of thumb that applies to those who seem to be having the most success: “don’t buy a business that isn’t immediately worth more the moment you buy it.” Typically that means bringing some tangible asset to the table. At least from what I’ve seen, expertise and advice (although important) are overvalued.

    Right now Tech is very much outside of our wheelhouse, as it’s a much more established remote working community. Any help you can offer to spread the word to those who can benefit is much appreciated.

  • kylagardner

    Thanks for the shout-out! :)

    And great assessment of why the DN docos are never that captivating. I’ve seen a few, but like you say, they aren’t really driven by any narrative. Based on the trailer, A Map for Saturday looks like it fares better in this regard.

    It’s interesting though “Saturday” still doesn’t get an audience outside of backpackers. I hadn’t heard of “The Beach” until I moved to Thailand. I’d argue “Rounders” is more known generally. Is there something about travel-related stories that makes people’s eyes glaze over?

    To dramatize ‘working online’ also necessarily suffers from the question of how do you make sitting at a computer exciting?

    As I work on the digital nomad thriller, my editor has had to remind me often that the digital nomad details will not be the tension/drama that propels my story forward. “I understand why you put this scene in here about him making his first dollar online, but this is….not a thriller.” More murder it is!

  • Jane Beresford

    ‘The Beach’ was successful because it’s a really well written, very visceral, book. The film was less successful in my opinion. A lot of the stuff I read about travel online is just indulgent and repetitive. And I guess this is a risk if you fictionalise it too. Ultimately who cares that your deal went bad because you couldn’t find decent wifi on Lombok?

  • Lol.

    I loved the movie too due to the visuals and the fact that it did do a little bit to capture the subculture of backpackers I had briefly experienced and lionized. What Rounders did even more bravely and it ultimately made it a movie that has endured and built a fanbase over the years: it didn’t dumb down the poker or the jargon for a mass audience. It towed the line of bringing a mass audience into the subculture and language without alienating them.

  • Yeah I’m tempted to say DN docos have been uniquely misguided due to something like…. the experience of realizing you don’t need to live the ‘corporate lifestyle’ for the rest of your life is so dramatic personally that it presents itself as something worth documenting in just that way. But it so far hasn’t worked. I guess it’s simply a cost thing too: interviewing a bunch of people who don’t mind being interviewed is cheap. Following a few stories over the years expensive.

    RE: the book…yes more murder indeed! Although do plant some easter eggs for insiders! :D

  • Jane Beresford

    In some ways I think a ‘Sex Education’ approach (Netflix) might work better for fictionalising the ‘DN story’ .. bit more ironic, fun.

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