Ten Ways To Be Your Own Boss

Like the Paul Simon song, there are probably at least fifty ways to be your own boss, but I only have twenty minutes this coming thursday at the 99% Conference and so I am going to talk about ten of them.

The super high growth startup that lands a ton of venture capital and heads for a big exit is the iconic entrepreneurial success story but it represents a tiny fraction of all entrepreneurial endeavors and I think it gets in the way of more people starting their own businesses. They think "well I can't do that" so they don't do anything. And that's wrong. 

So I am going to talk about ten ways you can be your own boss and hope to deliver the message that there is a way that most everyone can do it. 

Here are my visuals in draft form. As always, comments and suggestions are very welcome.

Ten Ways To Be Your Own Boss

View more presentations from fredwilson.

I'd like to acknowledge flickr member .eti whose most excellent photo graces the front of this presentation.

#VC & Technology

Comments (Archived):

  1. dangriffey

    Some great images – I’m guessing at the content but looks like some good examples.

  2. William Mougayar

    An additional angle to consider discussing is “How does one get there from their starting position”. These 10 scenarios are great as inspirational points, but how does one start making the switch?Nassim Taleb tweeted this yesterday which I liked: “The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”http://twitter.com/nntaleb/…

    1. AlanPearlstein

      I agree, its all about the fear of not gettng a paycheck. It reallly freaks most people out and I don’t think the vast majority of them will ever get past their fears,

    2. fredwilson

      What a great line from nassim. I.m going to add that to my talk!!

      1. Mike

        Any thoughts about the impact of the economic downturn and a rise in the # of startups? I know I fit this mold, where the ability to leave my current position was no longer an option so I decided to create my own at night and on the weekends. I’d assume others who actually do lose their jobs, and are forced to confront this fear head on, might finally be able to step out from behind this excuse.So I wonder if one of the best ways to be your own boss is simply just, “Lose your job”?

        1. Dave Pinsen

          “So I wonder if one of the best ways to be your own boss is simply just, “Lose your job”?”I mentioned this on my old blog last year, but it’s worth reading Scott Shane’s essay on entrepreneurship from The American (“The Start-ups we don’t need”). Here’s an excerpt relevant to your comment:[T]he typical entrepreneur is very bad at picking industries and chooses the ones that are easiest to enter, not the ones that are best for start-ups. Rather than picking industries in which new companies are most successful, most entrepreneurs pick industries in which most start-ups fail. So by providing incentives for people to start businesses in general, we provide incentives for people to start the typical business, which is gone in five years.And who is most likely to respond to those incentives and start businesses? Not the best entrepreneurs. We know that unemployed people are more likely to start businesses than people who have jobs. Why? Because they have less to lose by becoming entrepreneurs. After all, it’s less costly to you to start a company if your alternative is watching daytime TV than if it is taking home a paycheck from a job.The problem is that people who are unemployed also tend to perform worse when they start companies than people who quit their jobs to start businesses, probably because their bar for what kind of business to pursue is much lower. So policies designed to increase the total number of new businesses disproportionately attract the worst entrepreneurs.

          1. ShanaC

            I honestly think this is a much more complex issue than it looks like….based just on this observation alone

          2. Mike

            All good points. But I wasn’t coming from a policy perspective, I was simply asking a question about whether some good could come from a lot of bad. And attempting to point out that sometimes perhaps what people need most is simply a nudge to take that first leap of faith.Good article though.

          3. Dave Pinsen

            He was looking at it from a societal standpoint, i.e., does it make sense for the government to encourage most Americans to be entrepreneurs, and his answer, of course, is no. But whether Mike or Dave should be an entrepreneur is, of course, a different question.

          4. Mike

            “But whether Mike or Dave should be an entrepreneur is, of course, a different question.”Now that truly is the $64k question at the end of the day, isn’t it?I for one get to find out the answer to that all important question later this week with the soft launch of my first startup. Thankfully I’ve capitalized the business with much less money and anticipate making much more than what the article would classify as “typical”, so hopefully that bodes well for me.

          5. Dave Pinsen

            Congratulations, Mike. What’s the link, so we can check it out later this week?

          6. Mike

            Sorry it took me so long to reply, but getting everything ready ended up taking longer than expected. Anyways, here’s the link. Any comments would be much appreciated.http://bit.ly/dxzPrU

    3. Phil

      “The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”I’m 10 years out from having a monthly salary now, but the idea of one remains in the back of my mind. Though I’m better off having given it up, I still ache for one from time to time. Calling it an addiction is spot on.

      1. William Mougayar

        Anything that’s too comfortable is an addiction.

      2. enrolled agent exam

        He forgot nicotine. That’s a pretty bad one. :o)

    4. andyidsinga

      William – that is a great point. I can’t tell you how envious I am of myself in my 20s when I had a much smaller income and much less to worry about. I’ve worked in several startups, but in looking forward to starting one myself I see my garage as holding the most promise. The one advantage of a larger income is I own my own garage, and with discipline I can focus on my off “day job” hours and some of those resources to build something in there.

      1. Mark Essel

        There’s a growing trend in Jekyll and Hyde day-job/startups at night weekends to work towards traction or building compelling value.

    5. Mark Essel

      πŸ˜‰ to monthly salary

    6. bunkertank

      Great quote! I’ll translate it into French and post it on my blog and FB. The “fonctionnaire” mentality in France is astounding — this country is soooo counter-innovation…

      1. William Mougayar

        Genial. Nassim sera content…son doctorat a la Sorbonne porte des fruits. Envoie la traduction ici si possible, ca ne vas pas deranger.

  3. GlennKelman

    Glad you wrote this. What I worry about with venture-funded startups is that many focus on a business model that only works at tremendous scale: Avatar or bust. I’m always relieved when a web business can begin to make money with 1 million unique visitors or less. Sometimes the surest way to get big is to make it work on a small scale first.

    1. kidmercury

      yup. i honestly think we’re going to see a bunch of mega dot com meltdowns, and in the wake will be the small, niche, local businesses of the web.

  4. rosshill

    Would love to see the video with some audio to make sense of the images!

    1. fredwilson

      my hope is they film the presentations at the 99% conferenceif they do, i will post the video

  5. Fernando Gutierrez

    The visuals are great and most are self explanatory, but there are a couple (the boutique and the federation) that I can’t really understand.Will you post the video after the conference?

    1. Jing Jin

      Fred, beautiful deck for what looks like a great conference with Behance. I’m curious if you meant for some of the visuals to be later-stage versions of others: e.g. “federation” (Allen & Co.) for “boutique: (USV) and “company” (Twitter) for “breakout” (Foursquare).Also, to be your own boss connotes ownership – of your role at the company and the company at large, and, in financial terms, even shares in other companies. Many of the entrepreneurs here have gone on to invest in other companies as angels or VCs. This really blurs the line between “operational” and “advisory” work. Can you be an “owner” without being on the strictly operating side? To Mihai’s point, can the lawyers, bankers, and consultants of the world ever be their own boss?

  6. charlessmith

    What about the Scrambler? Someone who might work for/in any of those examples.

    1. fredwilson

      the scrambler! is that you charles?

      1. charlessmith

        Was thinking along the lines of graphic designers, iphone developers etc., but sure, I’ll take that label!

  7. paramendra

    The Project (Avatar) is looking interesting to me. πŸ™‚

  8. Jan Schultink

    Some of the slides I get, some require your live explanation.Maybe add a page with the cover of Seth Godin’s Linchpin to discuss how today’s education is (still) churning out people to fill cubicles and buy factory output.Small comment: the image on the Federation slide is “squeezed”. Unsqueeze it and put the text on the grey area of the road.

    1. fredwilson

      good suggestioni will do that

  9. ACM Johnson

    As the investor in the lineup, will you say something about the financial resources required for each of the 10 ways ? Not all projects can be done Ycombinator style. If you have time, a discussion about location choices and their implications might be illuminating.

  10. Mark Essel

    Argh phone flash fail! Forwarding this to Michelle, she could use some alternative thinking to frustrating employee/victim (clinical molecular biologist)

    1. ShanaC

      Awww, that is so sweet. (sorry)

  11. Dan Ramsden

    This will probably exceed the scope of the presentation, but I wonder if it’s worthwhile addressing what “being your own boss” actually means. There is an implied independence, or self-sufficiency, but this is rarely true. Even USV has limited partners. And Matt Drudge has his target audience. You always gotta serve somebody.

    1. Fernando Gutierrez

      Completely true. When I left my job to work only in my company (I had started it a couple years before on nights and weekends) I realized that I had much more people to report to: clients, employees, suppliers… the bank. But it is also true that those are a different type of dependencies and you can be free while you have them.

    2. Ahad Bokhari

      Good point Dan, I totally agree with you. Seriously your own gig requires alot more management, focus and client engagements..

    3. Nathan Hurst

      Right. If someone just wants to be their own boss, they could just open a new Subway restaurant. There’s nothing wrong with Subway. I’m eating one of their sandwiches right now, but to me, being an entrepreneur implies affecting the world in some novel way.

      1. andyidsinga

        Nathan – interesting point, and consider this: my 20 something step son (who I’m very proud of) currently manages and will eventually own a subway. He’s building skills and learning a lot – but he doesn’t seem so interested in affecting the world right yet. IMHO this kid is an entrepreneur in the making because he thinks about everything in terms of how to run an successful business πŸ™‚

        1. Mark Essel

          He’s picking up management skills and confidence in executive decisions. Until he locks onto a different direction Franchises are a great way to go. I couldn’t imagine executing a proven system for someone else for a fraction of the profit, felt too similar to being a branch manager.

    4. fredwilson

      yes you do

    5. ShanaC

      Determining your own destiny by being in service to something greater….

    6. Mark Essel

      Being your own boss has more to do with decision making ability and ultimate responsibility than it does with independence. I’m working to craft my dream business/job. I can’t imagine doing that in my day job/industry.

    7. Dave Pinsen

      Not if you’re retired, or on permanent disability.

  12. Ahad Bokhari

    Thanks for the presentation Fred and Business Insider, however i was expecting a little more depth. I visit your site frequently, good to see Disqus going here..

  13. ShanaC

    I like Albert and Susan, and I like the Daily Lit, but Albert is mentioned Twice, and I have a feeling that “Husband and Wife team” is “the Family team” and whatever lesson you want to apply there would be true for a father- daughter, father-son, mother-daughter, mother-son, two siblings, gay/lesbian partnership team in the sense that at the end of the day- the partners live intimately with the other person on many other levels. Are there other options of companies that drive at that point so that it is easier to identify with the core issue of many layers of intimacy within a company’s founders?

  14. Mihai Badoiu

    I’m surprised there’s no consultancy as an example.Partnership, McKinsey and co.

  15. MartinEdic

    I like this because it shows a range of start-up models. Today you can literally start up with no assets other than your creativity, persistence and time. A lot of us have no other choice because our skills don’t fit into a job description!

  16. Oo Nwoye - @OoTheNigerian

    I think it is important to get people to take the first step. Let them make something, anything. Even if they make only $10. That first step is REALLY hard!

    1. Mark Essel

      Great post -> caught it via @Scobleizer & @tristanwalkerTime for you shift those odds. I hadn’t thought about what the psychological effect of role models could mean on the outlandish task of building a startup. I used to think guys like Bill Gates, Steve Jobs/Wozniak, Sergey Brin & Larry Page were just super lucky geniuses. Now after learning much more about their paths, I realize they are mad, frighteningly hard working geniuses who built their own luck (or at least amplified it).

      1. Oo Nwoye - @OoTheNigerian

        Yeah, it means a great lot to have role models you can identify with. Thanks a lot!

      2. ShanaC

        It is really hard to develop a community of role models though. That’s really important.

  17. ShanaC

    Also really small point- Naveen Selvadurai name is missing a space.

    1. fredwilson

      only in the slideshare versionit got smushed when it was converted

      1. ShanaC

        I see. Well, the slides are beautiful. Did you get a copy of Slideology?

        1. fredwilson

          nope, i just keep learning from this communityevery time i do one of these, i listen to the feedback and get better atthis

  18. Mark Essel

    Ok Chart review goodies:.eti has me wanting a full scale setup of that officeSlide 2: Props to JLM for the madness crossover with genius. Of course that mad genius better be travelling consistently towards the future he/she makes an inevitability.Slide 3, 4, 5: embodiments of specific styles to founding. Probably make more sense with the context you give themSlide 6: beginning to see the awesome of the Boutique approachSlide 7: Federation: this has much greater potential with distributed startups (Automattic?)Slide 8: Project: perfect example, but huge force of will, hard work, and team collaborationSlide 9: Tour Bus: not sureSlide 10: The classic StartupSlide 11: Breakout: explodes out of an idea and an existing network? Fantastic sprint before SXSW when they first launched.Slide 12: Company = how does this differ from the Startup. They shifted gears big time.Slide 13: Questions: Plenty (see above) :DWill read through the rest of the comments quickly now to get the answers I need.

  19. Dave Pinsen

    I’m not sure how James Cameron, Twitter, and Union Square Ventures, etc., exemplify “the message that there is a way that most everyone can do it.”

  20. stevenwillmott

    Great examples – I guess an important dimension that transcends all of these is that you have think and act as your own boss. In all of these situations: have your own direction, own focus and make things happen (either as an individual or a team). You can be in any one of these structures but if end up mimicking the competition, being sucked into stuff which isn’t your core mission or compromising your values etc. etc. you pretty soon end up stop being your own boss.+1 for having the video up if/when there is one πŸ™‚

  21. Matt A. Myers

    “Entrepreneurship exists in the tiny space between madness and genius; and, its journey requires a few cross border violations across both madness and genius to get to the final destination.” – JMLAhhhh. That comforts me. πŸ™‚

    1. Matt A. Myers

      P.S. Anyone know where I could find a 99% Conference ticket? Says sold out on website. I’d really like to go to it. Wish I had heard about it sooner.

      1. Mihai Badoiu

        Isn’t that what b-schools do?

        1. Matt A. Myers

          I don’t follow? Unless you mean show scarcity by showing sold out, and then tickets magically become available? πŸ™‚

          1. Mihai Badoiu

            Half of the HBS alumni founded or co-founded at least one company.It seems to me that one of the things HBS teaches is how to take risks.You may say that it’s the selection of people, but I don’t think so. Engineers are much more useful in the beginning of a tech startup, yet I bet there’s no CS department with anything close to that in terms of statistics. Moreover b-school graduates tend to pull a higher salary and start with debt, which makes it harder to fly solo.

          2. Matt A. Myers

            Getting a bunch of people with money and privilege together to brainstorm and who are trained or exposed to proper techniques for business can easily apply those to many new emerging areas – I don’t think that makes them entrepreneurs. I really wish there was another term to show the difference.I come up with new ideas every day, that are good, and that fit into my current plans. Perhaps I’m just trying to feel special and separate myself to not feel threatened by academically trained folk. But most commerce students I know don’t know jack though about the real world.Personally how I deal with risk is I predict / see where the competition will be and come up with a solution that will solidify my place; That’s been the main motivator in furthering my ideas by being forced to think things through further as I’ve always planned to need an investor at some point. Anyway… doing it the best possible, and figuring out a way to do every part needed, is what will determine success.. laying the groundwork for what will be in 3-5 years.I have some mentors at the moment too, but they don’t understand social nor see the big picture as well… Luckily for myself, and a few investors that exist, most people don’t have this thinking so they are blocked and is why there is room. … even with all of the current competition that exists there’s a lot of money that relatively easily be made, just need to execute it… “99% perspiration” right? πŸ™‚

  22. sachmo

    Very much like the quote on slide #2.

    1. fredwilson

      that comes from the AVC community member JLMi get all my good stuff here in the comments

  23. Darren Herman

    Is that a Yobel Parra painting for Twitter?

    1. fredwilson

      it’s a paul klee painting from 1917http://www.moma.org/collect…<http: http://www.moma.org=“” collection=”” object.php?object_id=”37347″>check out thename of the painting Darren

  24. Tereza

    I’m reading this at 1am while finishing a consulting presentation for a client……..and reminded that Seth Godin said in Linchpin that you have choose between being a Consultant or an Entrepreneur, that you can’t be both and if you try, you’ll be unhappy, because they are in conflict.And he says the key difference between being a Consultant and an Entrepreneur is a Consultant gets paid only while s/he works. An Entrepreneur can get paid while s/he sleeps.Also, consultants are turning into essentially temps who are getting crushed on price. Only a small number of consultants will be able to be “The Best” and garner the high fees.I think that’s a really important distinction and I’m not totally clear if the presentation goes there. I feel it would be remiss if it didn’t, especially because I see so many people saying, “Hey! I’ll just become a consultant!!”. I’ve done it for many many years. It’s not so easy.Back to my consulting deck now….and boy do i want to go to sleep. πŸ™‚

  25. Tereza

    In typical form, that quote from JLM is a keeper.

  26. John Lynn

    Interesting deck and presentation topic. Although, I thought the 10 ideas you offered were going to not require the huge startup capital. Unfortunately, half (or more) of your slides are ones that would take a large amount of capital.All of that said, I love and I’m living the concept. Been blogging for the past 4+ years and it’s grown to the point that I quit my job a week and a half ago. Always makes me laugh when I tell people I make money blogging. Of course, they translate this to, “You make money writing stuff online.” They just don’t understand.Of course, now my blogs are mostly on auto pilot, so now that I’ve quit my day job I’m working to build other internet properties to add to my income. I call my blog income my base pay. Then, my other online work will be like my bonus.I should also make note that I’m doing this with a wife and 3 kids who all rely on my income. That’s my “tiny space between madness and genius.” Of course, the real genius in all of this is that my wife and I have been able to keep our personal/family “burn rate” lower than most people. A lesson taught by an outstanding professor in college.

    1. fredwilson

      i think the only ones that take a lot of capital are the last two

  27. Louis Berlan

    I love the slides, but I hope we get a video feed – obviously there are going to be some pretty great stories behind them!

  28. Charlie Crystle

    I couldn’t review your slides because of Apple. I was at a conference where there was no wifi. So I had my iPhone. Slideshare runs on Flash. Apple blocks Flash.So here are my comments, finally.I’m working on my latest company, but Apple doesn’t want me to succeed, apparently. Over the past 9 months I’ve developed a new app in the development tool of my choice, which runs on all PCs and Macs.It won’t run on the iPhone, iPod, or iPad because Apple has arbitrarily, cynically, and anti-competitively blocked Flash and, in its place, a Flash emulator from running on their device OS. Not because it can’t work, but because Jobs is, I have to conclude, an anticompetitive asshole making a land grab.I contend it isn’t their right to do so. I’m no lawyer, but it smells like a great case for the DOJ. This will cost me 5 months of delay. (Sure, I could have built it natively, but why maintain multiple code bases when native makes very little difference for your particular app? Should we all build using Assembly?)

    1. fredwilson

      don’t even get me started on applethe stuff they are pulling right now is nuts

      1. Charlie Crystle

        I’m hoping to get somebody started :)working on an editorial…

      2. Charlie Crystle

        I’m hoping to get somebody started :)working on an editorial…

  29. ravisohal

    You’ve probably already given the talk but I’d say add an 11th slide — the customer is The Boss.