How Much Should You Be Worth? Many Paths to Becoming a Multi-Millionaire!

As our readers know, we don’t tailor our writing to regular people and instead focus on ambitious individuals interested in living an exciting life. Everyone has a different lifestyle they are looking to maintain and we’ll go ahead and provide a framework for how we think each year should stack up at minimum.  We give up at 35 years old since no one should be giving life advice to someone in that age bracket (they’ve already made their decisions).


1) The first assumption we make is that you’re going to generate at least $100K a year out of the gate. If you’re working on Wall Street, within Enterprise Sales or in Silicon Valley, this is absolutely attainable. This is what we have recommended for a long-time in terms of a starting career.

2) Next, we assume that your net worth is calculated on POST tax money. We think it is a fraud to include $1 million in a 401K as $1 million to your net worth (it’s likely closer to $700K if we assume a 30% tax rate). To keep this estimate conservative, we assume all money in your 401K is worth 60% of the face value (40% tax rate).

2) We also assume that you will get a 5% 401K match. This is a rough estimate and we assume you’re not going to invest in excess of the match because you have better things to do with the money (primarily starting a business)

3) We use basic tax brackets since we don’t know where you live. Specifically we’ll assume everything up to $200,000 is taxed at 28%, everything between $200,001-$400,000 is taxed at 33% and everything above $400K is taxed at 40%. As an example if you made $400K exactly, we assume your tax bill is $122K (this is $200K times 28% and the other $200K times 33%). Again, this does not perfectly match the tax brackets to avoid perfect calculation and keep it simple.

4) We assume that your living costs increase at a rate of 5% per year and you’re going to live with roommates when you graduate in the first place. There is no reason to be a big spender when you’re young since we live by the saying “learn in your 20s, earn in your 30s, burn in your 40s”.

5) We assume your after tax investment returns will be 5%. This means the money you have on the sidelines will create 5% in annualized returns every single year. If you’re dollar cost averaging into the S&P 500 you should be able to generate around 7-10% over the long-run so our 5% assumption is quite conservative.

Example 1: Mixed Income Stream (Most Common)

From what we’ve seen, the most common path is this one. You start a high paying career, get burned one year on compensation, start a side hustle and… voila! Well over $2 million dollars by 35. Below is how it typically works out.

Age 21: To keep the math simple we’re going to assume you begin working at 21 years old. This means you’re likely graduating from college (despite costs rocketing higher!). In addition, we’re going to assume you have $0 in total net worth. If you’re reading this and are on track to rack up $100-200K in student loan debt, we suggest quitting entirely and reassessing why you’re going down the path of shackles. Since you’re going down an ambitious path we assume you’ll start with a Base Salary of at least $100K. This is going to be conservative given the compensation numbers for high earning careers on Wall Street, Silicon Valley and Enterprise Sales.

This is going to be a terrible year. You’ll realize that the cost of living alone is likely around $54,000 at minimum even when you live cheaply. Your after tax savings will likely be a smidge higher than 20%.

Age 22: To keep you motivated most companies offer a pretty nice income hike from year 1 to year 2. This is not because the company likes you. This is because they likely lost money on your participation in the labor force (training costs etc.) and if you leave after year one, they have to write it off as a loss or a bad hire! Ever wonder why employers care so much about time at a firm? Well now you know. They really earn money off of you once you’re up and running, not when you’re green.

We assume you get a 20% hike and because of this you’re still motivated to work. You put away just over 25% of your gross income a big step up when you look at the year-over-year change in total after tax savings (59% increase!).

Age 23: At this point most companies give a similar pay raise on a dollar basis. This is enough to keep employees motivated and they are now in the green on their investment in human capital (you!). Since you’re still seeing some career progression and you’ve got another wage hike you’re feeling pretty safe in your position making it easy to continue slogging along. The one thing you do notice is that the people who have been there for about 5 years seem to be more bitter than the younger employees.

Since the dollar amount increase was the same, your total compensation is up 16.67%. You end up putting away ~31% of your total gross income and your net worth should clear $100K. Unfortunately, around this time year 3 to year 5 time frame, you’re going to get hit by “the system”.

Age 24: You get one of the following excuses: 1) we had a bad year as a firm or group, 2) you’ve been getting solid raises so you should take one for the team or 3) we don’t know if you’re ready for the next change in role. It does not matter what the excuse is. Your compensation is going to be flat. It could be up (barely) but the point is the same, you realize that you’re a COG in a system that doesn’t care about you at all.

Hopefully this terrible conversation happens earlier rather than later in your career. This is because you’ll have the energy and motivation to do something on your own. You’ll strike out and do something small (typically free lance consulting) and make a few bucks with minimal effort. Total savings is still in the low 30% range.

Age 25: You get a small hike, but the move is not great, you’re realizing that you’re solidly in the center of the “triangle” within the firm where it is hardest to move up. Everyone wants you to quit or fail because it will lead to less competition for them over the long-term. You stick it out anyway and realize that it will be a while before your next “step function” upward in compensation. The silver lining is you can continue to freelance.

Your time is spent either freelance consulting or you’ve figured out that you can start a full business selling products! The result is largely the same, you focus more on your business and generate well over $1,000 a month. Not bad! Total net worth goes to $200K!

Age 26: You’re solidly stuck in the middle of the Company/organization. You look around and everyone in this bracket between 26 and 32 or so years old makes the same. It’s depressing to see and you realize if you jump firms… well it’s going to be the same story! May as well remain in the same Company if you’re plugged in from a political perspective. Besides, working on your business makes the most sense given the returns you’ve seen over the last two years.

You begin shirking a tad at work, cutting corners when needed and grow your small side business to $25K in total profit. It’s now generating a *near* living wage! You don’t have time to burn your cash since you had to work hard to get here. Net worth $300K

Age 27-31: This is probably the most painful bracket. You’re going to be doing the same mundane work for the vast majority of the time. The guys you want to replace won’t quit and there is no slot for you to fill. Your only upside is from your company. It’s tough to stay focused because the business you’re running cannot be scaled easily due to your current necessary career schedule! You’re going to feel like you’re chewing through a concrete wall.

The good news is that you’ll be able to chew through the walls without killing yourself. You’ll grow the business to an official near living cost profit pool of $50K by the time you’re 31. Lucky for you, since you have a career still it’s pure profit! Net worth $850K+

Age 32: For some reason this happens. When you’re about to quit because you see the light at the end of the tunnel you’re given some change in role. Think about it like this… If you were smart enough to realize you’re being underpaid… and were smart enough to start something… you’re probably a better worker than those guys slogging in long hours with nothing else going on! You’re hard working or you’re smart. You can’t be both.

For fun, we’ll assume you get promoted to a new role and your business takes off at the same time. This creates a tough situation for you because you’re not about to walk away from that high income boost and you can cover your living costs off of your business! You typically stick around “just one more year… just one more year…”.

Age 33-35: Your business cannot move anymore. It’s growing at a minimal rate of just 10%. Your income from your career is still the majority of your earnings. The problem is that working for someone else is becoming a hassle. You can’t stand taking any orders. Everything at work makes you annoyed and you’re going to take your foot off the gas more and more. They typically try to motivate you with more money but at the end of the day, you get blown out once they realize you’re not tied to them.

Reminder. Under no circumstances does anyone know what you’re doing. You simply get blown out around 34. The best part? Your business ends up benefitting because you never really focused on it. Typical net worth? Multi-millionaire at $2M bucks (Click to Enlarge Image)

Pic 1

Example 2: The Career Man

Some people just never see a reason to start their own Company. The reason why? Their careers never see a bump or hiccup. Specifically, a lot of luck goes their way and they have the skills to fill in each leg up of responsibility. We’ll use our Investment Banker as the best example since we know a few people who have pulled this off.

Age 21: Top –tier investment banking analyst. You’re the best in the class in the right  group/sector and you’re going to get paid at the top. Roughly speaking this is around $150K for a first year and you’re going to have the same living costs as everyone else ($54,000 out the gate). You are able to save your entire bonus so your savings rate is pretty solid at $57,600 in post-tax money in year-one.

Your savings rate is already over 33% when compared to your gross income and you had to work hard to get the top-bucket. No vacation for you, just deal related activity and a smile on your face even when getting crushed.

Age 22: It is rare to fall from top-tier in year-one to year-two. You end up being in the right “circle” from a political perspective and people in Wall Street rarely change their minds. You continue to get all of the right deal related projects and since you’re still focused, it is easy to get into the top-bucket again. Overall, you clear $175K in your second year without skipping a beat

It has only been 2 years and you’ve cleared $133K in net worth! Pretty impressive. While everyone else is wasting money getting drunk at the club you’ve built a strong baseline for a career that could lead to an associate promotion!

Age 23: After a somewhat easier year 2 you decide to begin training all the first year analysts. You also attempt to participate in more drafting sessions (proactively) dropping hints to the higher ups that you do have what it takes to be in an associate role. You’re able to manage the younger analysts and you have ideas for updating slide decks and S-1’s without any push to do so.

It has now been three years and you get the head nod for the promotion. Your net worth is nearly $250K (not quite) and it has only been three short years..

Age 24: We are throwing in a low number as a transition year. Why? Typically, you’ll either get a meaningless stub bonus or you will not get paid the exact top tier bonus from Analyst 1 through Analyst 3. This is a precautionary measure to make sure the math still adds up. In addition, many analysts typically upgrade their housing when they are moved to an associate role.

Overall, we take a small step back to keep all estimates conservative.

Age 25: Your first year as an associate requires more proactive work from you, you’re updating projects before you’re being told to do so. This means you know what your MDs and Directors want to see and simply save everyone time by putting all the items in there before it is requested. In addition, you’re consistently training the junior staff. Nothing special in this year but you’re clearing $230K (at least!).

Age 26-27: These two years are quite similar to age 25, the difference is that you’re continuing to show leadership in the form of training and initiative with pitch books and live deals. In addition, you spend some time at industry conferences to build a small set rolodex of contacts in your industry. More importantly, they give you the role of “staffer” right at the end of your third year as an Associate. This is typically given to VPs (most firms) so the writing is clear. If you can manage the team well, you are in-line for a VP promotion.

Age 28-29: Around this frame they give you a promotion to Vice President. You did the necessary work and luckily you built a small contact list within your sector. You get a material “step-function” up in your total compensation to $400K with a green light to $500K the next year. By the time you’re solidly in a VP role you’re also solidly in the 7 figure net worth range.

Age 30-34: It gets extremely difficult to predict in this range. However the general set-up is as follows: 1) you execute several deals – didn’t source them, 2) you sign up a few small mandates, 3) you eventually win a couple of extra small M&A deals or lead an IPO sourced by an MD, 4) you sign up more retainers for other ideas such as registered direct transactions, poison pills etc (small stuff), 5) you eventually close a couple of nice M&A deals or get lucky and are the banker for a specific IPO. The long-story short is you generate enough revenue to warrant a director promotion but not quite good enough to get to MD! You clear $500-600K each year. By the time you’re all set and ready to quit, you’ve got $3M in the bank and you start a hobby to make some side income. (Click to Enlarge Image)

Finally, most people don’t quit. If you were this good you’re likely a career banker.

*Note: for the 401K contributions below, we assume you are never able to contribute more than $18K which is the current max, hence the $36K cap at age 28 and beyond*

Pic 2

Example 3: The Entrepreneur

This is where the real money is, we’ve seen several people quit their careers rapidly once their companies begin to gain traction. It is tough to work for someone else when your business is making more money than your career!

Age 21: You start your career and begin acting like an entrepreneur out the gate. Instead of wasting time with politics (big career mistake!) you simply get your work done and go home immediately. This does not look good to the higher ups but you don’t care as you’re already working on something on the side. You save a decent chunk (just over$25K).

Age 22: You get an “okay” pay raise that is in-line with everyone else at about 5%. You realize pretty quickly that there is more than performance that matters at work. There is something called political capital where you have to be liked by the “right” people in order to get the better payouts. Fortunately, for you you’re still seeing 200% growth from your business so it remains as a focus point for you and you triple it to $15K net of tax.

Age 23: You’re solidly a “median” employee. There is no hiding from this fact. You can’t really get laid off or fired because your work is solid and good, you just don’t play any of the political games within the firm. Luckily your business doubles again, because this is why you don’t have time to play the politics in the first place!

Age 24: The step function occurs! No not for the career you hate but for your business. You clear $75K in post tax money which is roughly equivalent to what you made at your career. You’re thinking about quitting immediately but the firm has no reason to cut you. You’re a top tier performer from a work perspective but you take no initiative because there is no reason to anymore and on top of that there is no incentive either! Funny situation around this age as you’re not willing to give up all that money and you’re not willing to go all in on your business either.

Age 25: Your business now starts making more money than your career and you hear of a Reduction in Force (RIF) that is occurring over the next year or so. You raise your hand for the RIF since you don’t care about the career anymore. Once you raise your hand, they add your name to the chopping block (so you think!) and your business is doing great almost at $100K!

Age 26: They don’t let you go! Unfortunately, when it comes to cutting people its actually harder to get rid of the top-work performers even if they are not motivated! You end up getting a long-winded pep talk about working harder and are handed a ton of work that will double your hours at the firm. You quit. Forget about it you say and you walk away. Your business ends up generating $135K that year.

Age 27-35: For those skilled enough to build a 6 figure income while at a career, they usually end up scaling to around $1M in net profit. For some reason this is around where it all shakes out. You can certainly exceed this number or watch the number flat line. Overall, getting to a million dollar business is possible and this is where we assume it all shakes out. You’re growing your business in non-linear fashion and end up getting to a $5M net worth at age 35! (Click to Enlarge Image)

Pic 3

Concluding Remarks

We’d like to take the time to highlight a few key psychological factors for people looking to become multi-millionaires.

First, you will get screwed at least one or two times. There is no escaping it unless you’ve go the luck of the Irish. You’re going to get burned pay wise or work wise somewhere (typically 1-2x) over a decade time frame.

Second, once your business income exceeds your work income your motivation falls off a cliff. You don’t care about doing anything beyond the minimum and quickly fall out of the “circle” politically.

Third, If you’re spending your time building income streams you can get to multiple millions of dollars by age 35 and the numbers clearly prove this out (even with 5% cost of living increases!)

Fourth, if you don’t focus in on building yourself up early, there is practically no way to catch up.

Fifth, we don’t have much time. There is a 20 year time frame at maximum to really make money. No one wants to be killing themselves working around the clock at age 40+

Now that you have a clear path to a high net worth, we can recommend Personal Capital to track your progressThe Company offers *free* software tools with the following four key features: 1) ability to avoid losing money by tracking all fees associated with an investment product allowing you to choose the best possible fund for your future, 2) portfolio analysis where your risk profile is stacked up against your current age and retirement goals, 3) in addition to these free tools, you can also track your net worth and path to becoming a millionaire and 4) when you hit $100K in networth you’ll receive a free one time consultation with an investment professional at Personal Capital. After linking up all of your accounts you’ll be able to sit back and watch as your net worth goes up and your fees remain minimal over the next several years. We strongly believe that Personal Capital is the premier personal finance software tool when compared to its competitors such as Mint.


  1. goldteefgod says

    Top-notch content, as always.

    Would love to see a forum added to this site, with “extreme vetting” for membership, of course.

  2. Michael says

    Been following the advice here throughout university, amazing post as always. Non target school but I landed a IB boutique internship and I’m on track to graduate with 20k in the bank.

    Just accepted an offer at boutique PE firm in NYC. Only 45k a year salary, plus bonus on performance. But it’s only 9-5 so no reason why I can’t spent 2+ hours a day building my network… I’ll be free to bring in my own deals at this firm. (already got one)

    I know it’s not the typical path, but I couldn’t get into BB from my school. No reason why I can’t get out and build my network and bring in some deals!

    Maybe I’ll network and more and see if I can go back into IB if this doesn’t work out…

      • Michael says

        Yeah, it’s a pretty small form (20 people) mostly ex-BB bankers, they have only grown enough recently that they could hire me on, with a salary. I’ll be monitoring their portfolio companies, modeling, writing IMs / business plans. The firm is sort of an umbrella for the guys working there. It’s very entrepreneural and they all bring in their own deals.

        The principal is a graduate from my university and has been my mentor for 2 years or so. I’d be basically taking on most of the tasks that would allow everyone else to focus on bringing in more deals.

        If everything goes well I could become a partner myself in 2 years. I’ve already gotten a contract signed to raise $1m for a startup so, I’d get a fair bit of the 50k fee from that since I’ve done all the work!

        Or maybe I’m just rationalizing it… I do trust my mentor (the principal) but I do intend to network more and hedge my bets by looking for IB or other PE positions…worst case is I lose a year here and it doesn’t go anywhere, but then I move to a better role, with the work experience in both IB or PE…

  3. says

    Another solid post, as per usual!

    If you keep regularly dishing out such quality content, I truly wonder what great *secrets* are in your upcoming book!

  4. IllmaticFTW says

    Good post and one I wanted to read for quite some time but this post is a full on reality check. For a while I was insecure about my situation as a 24 year old who has had a tough time getting it together and wondered just how behind he was, things don’t look too good but we all have to start somewhere.

    I started reading WSP my final two years in college and took the pill, woke up, but realized how badly not only I had messed up but how much outside factors were messing me up. I had overbearing immigrant parents that shoved me down the med school route despite my grades not being high and then kept me at it, hard to reason with stubborn immigrant parents but your post about family and dark truths about life really woke me up.

    Graduated college without good grades and realized how worthless a Biology degree truly is, on top of being quite difficult. Had to move back in with parents who were trying to push me down the PhD (hell) field but thanks to your post, I had the guts to tell them to fuck off and tried to find a way out of my horrible situation.

    Read this blog through and through, realized that Sales is the way to go and I had a degree from a top 50 university that is well respected.

    Just recently I landed an offer and will start making a decent salary in a low COL area where I have some friends and family. At 24 (soon to be 25), I feel like I am way way way behind compared to the examples on this thread but we all have to start from somewhere. Have thought about getting an MBA from a top school at some point but not sure if that would be a good decision now.

    Thanks for this post, this blog has been on fire lately!

    • Wall Street Playboys says

      Seems incredibly irresponsible to go down the med track if you can’t get in unless they are footing the bill.

      No need to measure to the numbers here, these are just 3 examples of typical “paths” that we’ve seen multiple times.

      • IllmaticFTW says

        Well that was the good part about it, they were footing the bills so I came out no debt but it took longer for me to finish college and I am approaching 25 about to land my first job offer. Seriously feel like I am playing catch up from here on out compared to the kids who took 4 years to graduate and got a job right afterwards.

        The difference between 25 and 23 is like day and light, sometimes I wonder if 25 is way too late to really get going since so many 22-24 year olds reading this blog are going to make serious cash. They don’t call it a quarter life crisis for nothing!

        Gotta say though, without WSP’s recommendations about sales, I would be toast for the most part. Your post about finding your skills and what kind of intelligence you have was career goal.

  5. BobRob says

    Do you seriously consider someone after 30 as a lost case? Not everyone had luck to see that blog when they were 20.

    • Wall Street Playboys says

      It says 35. Around 35-45 if they aren’t making the right moves cash it in it’s over.

      We put the low end because we’re all racing against the big headwind. Time.

      Never assume we have time. Always push the timeline *forward*. Always.

      Side note, check out Felix Dennis’s book. He sees the same, after 40 if too lazy to have started a business they never make it.

      • Markximus says

        I disagree with this, it just means that you have to take on more risk to play ‘catch up’. Networth is not linear and based on events.You’ll understand this when you encounter it. You can still make it out if you can handle the risk and be prepared to lose (which most people are not). Starting a business and being an entrepreneur is truly a great equalizer.

        Bobrob, it’s not about being lucky to see the blog. You could have figured this out yourself. Though WSP’s posts definitely speeds up the learning process.

  6. Nixon says

    Saw your tweet asking for examples of friends who have made it to the top. Let me give a story about myself based on a recent interaction with a friend.

    First, I’m admittedly 35 so I may be on the high end of the age range here. I’m one of the 10 or so highest ranking execs at a large financial company with all-in annual comp in the $750K range ($250K base, $250K cash bonus, $250K max stock bonus). I also have NW in the seven figures and own 35 rental units.

    I don’t come from a top school but have hustled my way to the top and sacrificed my 20s to position myself to this spot.

    I still keep up with some of my best fraternity bros from college and one of them has a sidegig/product idea that he wanted to run by me as he knows I’m successful.

    I gave him feedback on where to take this sidegig next and he told me he didn’t have the time or money to take it to the next level.

    This friend just bought a brand new $40K truck and a new house that he doesn’t need. He also works *maybe* 45 hours a week and routinely spends his weekend watching sports.

    I told him he’s lying to himself if he thinks he can’t make time or find money to invest, he just needs to change his habits. He got pissed and we haven’t talked since.

  7. Mob Barley says

    Or go all in on one enterprise after another. I don’t think anyone fails after starting 10 legitimate businesses.
    This advice is for the people willing to really get their egos thrashed hard.

  8. D-Train says

    Wish I had this advice 10 years ago.

    “You look around and everyone in this bracket between 26 and 32 or so years old makes the same. It’s depressing to see and you realize if you jump firms… well it’s going to be the same story! May as well remain in the same Company if you’re plugged in from a political perspective.”

    I’m in this exact position right now. I recently found this blog so didn’t read the office politics guide. I dismissed my coworkers as try hard or suck ups and didn’t want to stoop to their level sucking up to the boss. I paid the price. Just got year end compensation that was much lower than expected. Only way to get a raise will be to jump ship in which I’ll have to start the political process all over again. Won’t make the same mistake twice.

    • Wall Street Playboys says

      That is painful, definitely time to jump to another firm hit reset there and start a side business.

      Never know how it can turn out so you need another form of income asap. Once you have at least 3 (livable wages) you’re good to go.

  9. says

    Great analysis. Too bad it is a little bit late to follow this path for me. Still I believe it is never too late to start your own business, although you wont be exactly burning cash in your 40s.

    Better a little bit late, than never. Most people spend their entire lives in cubicles.

  10. McBird says

    God damn. Y’all are on some Christina Aguilera genie in a bottle type magic shit.

    I took the entrepreneur route. Dropped out of a premiere business school to go full-time at an ecommerce startup. Worked an insane amount, didn’t make shit, but learned the game.

    Failed a few times, but now run a few different online businesses with more in the pipeline. Diligently working to scale from 7 to 8 figures in my main company and then exiting in the next 3-4 years.

    I’ll be in my early 30s then.

    Basically if you’re approaching 40 and you haven’t done anything big yet, you never will. That’s okay for some people but arguing otherwise is futile.

  11. Ches says

    I know I am in not in a position to comment here but this site have helped me close that $3000 Wedding client (I know not much). I live in Manila
    where our living standards is 4x lower than first world countries. Just want to say a simple thanks.

  12. Jacob Johnson says

    Great post as always, I’m just a high school student wanting to become a investment banker after college. Not sure what businesses would be great to rack in money on the side but guess I will have to try in order to find out. Anyway keep up the good work. My new favorite quote is “You’re hard working or you’re smart. You can’t be both.” Thanks!

    • Invencivel says

      As stated on the blog a million times already, start learning copy writing ASAP. It will be the best decision you ever made. Trust me on this. It’s a license to print money.

      *Only after you learn how to sell* start thinking about starting a business. Trying to be an entrepreneur without knowing how to sell is a death sentence. You’re making your life 10x harder for no reason.

      If you don’t know where to start, google “gary halbert 30 day challenge” and stay away from blogs. Learn directly from the masters, not some guru desperately trying to sell you a $500 “copywriting course”.

      Good luck!

  13. ownmyhood says

    What a coincidence, 20 minutes ago I walked out of my bosses office after letting him know I’ll be leaving the firm (to focus on my biz). I’m in my early 30’s and am a millionaire.

    Kind of sad I’ll only be able to feel this way once…

    It’s amazing how much my late 20’s early 30’s resemble the “mixed income stream” model you guys posted. Gave me chills.

    Early 20s not so much, but a couple years as a starving artist brought things into focus (I’d be an example of someone who “turned it around” at around 24-25).

    Anyway, if any youngin’ in their early 20’s asked me how to become a millionaire (and I thought they had any potential, which few do) I’d send them this article. Pure gold.

  14. SP says

    Nice article.
    I’m turning 20 this year & I’m a bit ahead of the race. I’ve been working on path 3 since I was 16.
    I made tons of mistakes, but they were worth it.
    My sales skills are a bit weak, so I’m working on getting a sales job. Maybe even starting a YouTube channel.

    Anyway, this is a great article and
    I can’t wait until you guys release the book.

      • SP says

        I honestly think it’s a waste of time. It was a consideration as a hobby, but fuck it.
        YouTube is primarly good for entertainment and general BS self help advice. And I have no interest in either.

        I’m guessing that you had a bad experience.

    • AC says

      The majority of people who make money on youtube, virtually guaranteed, are the ones advertising on youtube channels. Don’t get fooled…

  15. Anonymous says

    Your guys’ shit is on point. Even if you don’t follow this to a tee you are still lightyears ahead of everyone else teaching English and “traveling” the world at 23-24…

    Since you guys gave me a lot of shit.

    Enterprise Sales (Software) typically goes —

    6 mo – 1.5 year BDR/Inside Sales 50-100k
    Enterprise AE can take up to 3-7 years to make typically from here depending on performance and the company, etc. 120k-1M…generally

    There is a LOT of variability and is not as cut and dry as Wall Street.

    Best way to break in IMO is spam apply to entry level gigs, talk to recruiters, attend networking events in Major cities (NYC has a bunch and some of them there are people who are CONSTANTLY hiring for good positions) until you get in somewhere.

    Or just cold call sales managers until someone says yes.

    • Milo says

      Thank you for your post. I work as a software engineer and would like to break into enterprise software sales.

      Could you recommend a few good companies to track down sales employees for on LinkedIn? I imagine this would be companies like IBM and Cloudera?

      Are the best networking events specific within the industry (e.g., hadoop) or are there a few general software sales events you recommend?

      And finally, does experience as a software engineer provide a boost in the application process for software sales jobs?

  16. J says

    There are many lucrative government contracting positions that pay 200k- 300k/yr. These jobs are usually very cushy and come with plenty of off-time. You don’t really have to go to Wall Street or consulting with an Ivy league . If you are not book smart nor you don’t have any interest in starting your own business, join the military and get an MOS that requires a high degree of technicality or clearance level. Once you get out, you will be able to land some lucrative jobs. Let’s put it this way, Uncle Sam spends almost 600 billion dollars annually on defense budget which is more than half of all the tax revenue he collects each year. In another word, Uncle Sam is the biggest spender in the word, so cater him.

    As a defense contractor, I am pulling in almost 200k/yr and half of it is tax free since I am working overseas. Next Year will be my 7th year in contracting, my net worth will hit almost 1 mil and I will be 34.

    • P says

      There are limits to this for future growth:

      1) Trumps cutting the gov’t support nexus. It meets his endstate philosophically. Politically, it weakens his internal opposition.

      2) The entire US DoD is transitioning from low intensity conflict to high intensity. Period. Contractor roles explode in low intensity conflicts. In a high intensity conflict, only contractors with software/high tech weapons maintainers (continuity) or sales of reliable platforms ( ai to replace joe in logisitics) will grow. All human security/intel/personnel support from civilians will be automated or taken from contracting

      3) Financially, US cant throw $ to solve problem in increasing interest rate environment. Debt services will limit r&d and all perks in dod. An example of reduced money flow is the transition away from the pension system( 20 years for lifetime 50% base salary wo market risk) to tsp/ ira match at 5% for a 20% pension cut(wtf!!??)

      BLUF: learn to sell imported womens cosmetics from israel or korea. They always get older and never b drafted

  17. says

    *** If anyone wants to discuss making money, business, careers, or anything related to this blog, join the Slack group by clicking on my username in this comment ***

    • Octadv says

      The link for the Slack group expired. I’m a media buyer. Not sure if i can leave contact info in comments, but a skype mastermind with like minded people from here would be interesting.

  18. RE Guy says

    A salient point:

    “First, you will get screwed at least one or two times. There is no escaping it unless you’ve go the luck of the Irish. You’re going to get burned pay wise or work wise somewhere (typically 1-2x) over a decade time frame.”

    “…the point is the same, you realize that you’re a COG in a system that doesn’t care about you at all.

    Hopefully this terrible conversation happens earlier rather than later in your career. This is because you’ll have the energy and motivation to do something on your own.”

    A predictable issue in my mind is that a young, naive, ambitious and hard working guy will assume that he can “give it his all”, create a ton of value and both him and his employer can make plenty of money. The problem is that often the employer is focused on himself while manipulating the employee.

    It can be weakness, ignorance, sloth or plain malice, but the employer will almost invariably screw over the employee at some point. And it goes without saying, so may business partners.

    It can seem strange when that person things “If we just cooperate and work hard together, we’d both make more money than this little bit you’re screwing me for?!” And they are right, many people sacrifice long term gains for short term by doing this.

    When it happens, rather than stay discouraged, the employee needs to see it as a signal to become self-sufficient and remain motivated in developing their own income streams.

    The issue is that emotionally the employee has expended a large amount of energy towards building something that isn’t theirs, so they will feel that loss as sapping their motivation, at the time when they most need to stay focused, disciplined and pursue a clear vision.

    Being young and having more natural energy and seeing your life as fully in front of you helps, as stated here.

    And importantly, having someone point this out here so that they can expect it, be prepared for it, and thus not have their enthusiasm drained (and perhaps use it as fuel for even more enthusiasm), helps.

    And, by building up their other income stream(s) already so they have another venture to pivot into already, is even better.

    Great post as always! Looking forward to the book!

    • ownmyhood says

      “And it goes without saying, so may business partners.”

      Luckily I saw multiple partnerships dissolve (not pretty) before starting my own biz and recognized that going into business with a partner is usually not a smart move, unless:

      -You and the person you’re partnering with have totally complimentary skill sets.

      -You and the partner are family members who have gotten along well your entire lives and know essentially everything there is to know about one another.

      It seems most partnerships formed by fledgling business owners are created out of fear: it feels safer to take that initial leap together. Then once the business takes off and the fear subsides almost inevitably one partner will feel slighted.

      Another common reason for partnering is one person contributes the capital, the other person does the work. Tempting for a broke young person with a lot of ambition, but largely set up to fail, regardless of the venture’s level of success.

    • Houston Portfolio says

      Thabks brother. You always post something enlightening for me to consider coincidentally right before I’m about to make an important move hah!

  19. says

    “It could be up (barely) but the point is the same, you realize that you’re a COG in a system that doesn’t care about you at all.

    Hopefully this terrible conversation happens earlier rather than later in your career.”

    First time I realized this was during high school when I worked at a smoothie shop in the mall. The internship and job hunt during college confirmed all of my suspicions and solidified that belief. Employers do not care about you. Do your own thing.

  20. tycoon says

    The 1st and 2nd example relates well to sam from financial samurai. He managed to get to a multi million dollar net worth by 35.

  21. Dagambler2 says

    I messed up early on and stayed with a tech corporate job (I’m 23 and will be 24 this year). But due to your advice on “10 years, no excuses”, I left my corporate job, am independently consulting for now, and transitioning into a sales job. I already have interviews lined up for B2B software sales jobs. I should be starting my first pure sales job in June.

    I hate the fact that I wasted two precious years of my life, but I’m gonna haul ass to be a millionaire when I’m 34-35. I was able to save about $20k, but I really wished I had found your website when I was 19 or 20 instead of 1 year ago. I will most likely be the mixed source income one since I have a SaaS business that’s doing about $700/month already and I’m gonna use my skills from my sales job to sell more software.

  22. says

    This is one of the best posts I’ve read in a long time, and also one of my favs from this site.

    So I’ve graduated 2 years ago, currently working in Ent Sales at a SaaS unicorn making $100k.

    I’ve started an ecommerce business 8 months ago on the side (2 hours/day on average since then) which has generated $130k in revenue with 25% net margin so far. I hate being an employee and have been planning to quit for several weeks already. However, my business solely depends on paid traffic and the performance can be vastly different from month to month (I had $10k profit months and then $2k the next month). It’s a roller coaster and I don’t know how long this will be sustainable if I don’t expand into new categories (which I could easily do), so that’s why I still haven’t left my day job.

    Any advice? Just take the plunge and hope that it doesn’t all fall apart while creating new businesses (=add more ecommerce websites) at the same time?

  23. ReasonFromFirstPrinciples says

    Example 4: The Extreme Entrepreneur ( …. Ctrl+F “extreme entrepreneur”)

    You gain admission to an Ivy League College and are headed down a path towards Wall Street. Mathematics and Economics double major. You are on track to graduate early. But. While at school you start drinking and partying too much. You get arrested for a DWI in your junior year of college. That summer, school informs you that you are suspended. School tells you to go “get your act together” and use the time “away” from school productively.

    So you leave school, at 21 years old, and get a job at Dicks Sporting Goods making $9 an hour. Your self-confidence is gone, the chances of that great career job at that investment bank you were eyeing are basically gone at this point. Your family and everyone that believed in you is disappointed in you. You start to hate yourself for destroying your own future.

    So you spiral into a depression. You become an alcoholic who drinks in the morning, afternoon and night to ease the pain of a *seemingly* failed life. When you reapply to get back into school, you write the application drunk. School see’s that you did not get your life together. They suspend you again for another year. When you get off the phone call, you immediately reach for the bottle. You are in disbelief.

    You lose your job as a result of your drinking. Depression gets worse. Alcoholism gets worse. Life appears to be over. This state continues for months.

    Finally one day you wake up from a blackout at 1pm and you hear a voice in your head that says ENOUGH. You go downstairs, admit that you need help (most humbling moment of life) and ask your mom to drive you to AA (because remember your license is suspended from that on-going DWI case). She does. You go to AA and decide to stay. Best decision you ever make.

    Around this time, you read a book called “How to get rich” by Felix Dennis. This plants the seed that you too can become rich and rebuild your life. You promise yourself that you will NEVER QUIT on yourself. You decide right then and there that you will get rich by building a business and you drop out of college. You don’t file any papers with school, you just walk away and never talk to them again. You try to start an internet business, with no experience and skills, and you fail miserably. You run out of money. You tell yourself, I will NEVER QUIT. Around this time, your DWI case is resolved and you get off with a traffic violation, a fine and a danger of drunk driving course. The seed that is planted by Felix Dennis starts to grow. You start to believe that luck is on your side. So you become willing to do whatever it takes to succeed.

    You humble yourself and get a job as a bus boy at the Marriot Hotel at 22 years old. People laugh at you. You don’t care. It is a start. You come home and apply to jobs every single day. You land a job making $20 an hour as an administrative assistant to the director of operations at a dialysis company. You live at home with your parents and you work every possible hour you can. Because you are incredibly intelligent, you accomplish all the work assigned to you in the first 2 hours of the work day. You then spend the rest of the day learning how to program (Ruby on Rails), build websites and scalable internet businesses. 7 days a week all you think about is your business that you will build. You stay at that job for 11 months, live at home with your parents and save $23,000.

    **You come across a website written by some rich douchebag on the internet that teaches you to see the TRUTH. You read every single post written – multiple times**. This accelerates your thinking years. Another stroke of luck.

    You quit the job by walking out on it. Burning the bridge so you can’t go back. You are willing to go to the death to succeed at your business. You then spend the next 8 months, living at your parents house, trying and failing repeatedly to get traction. Nothing catches. But it is okay. You are learning. Each failure teaches you more and more. You work 12 hours a day, 7 days a week. Then that fall, you start getting traction. You start making sales. So you push yourself even harder. You start realizing you are growing exponentially. **Most fear that you feel is gone**. You have stared down the worst that life can throw at you and you have come back from it. You are 24 years old. You start seeing a clear path. Your skills are starting to shoot thru the roof. You put all your time into learning and mastering paid media buying *AT SCALE* as it is the way to get rich as **fast** as possible in online sales.

    No going out. No girlfriends. No dinners. You drive a rusty silver honda accord 2002 with 153K miles. There is no heat in the car because the gas pipe has a hole in it and the smell of gas radiates thru the heating vents. You don’t care. When you drive you just wear an extra jacket, blair the music a little bit louder and LAUGH. This experience will only make you stronger.

    Nothing matters except your business. It is the only thing you do 7 days a week.

    Millionaire by 30? You plan on doing it by your 27th birthday. You are turning 25 in a few weeks (from today actually). You know it is possible because of the internet, your understanding of leverage and paid media buying. You build all businesses to be sold right from the beginning.

    People who hear this don’t believe you. They laugh at you – still. *Until* they start to see the *currently* small business you are running bring in sales. They have no idea what is coming. They are *unaware* of the power of mastering paid media on the internet.

    The real question is NOT who you will be at 30. The real question you ask yourself is who will you be at 45, 55? All progress is exponential and you realize that there is no limit to how far you can go.

    Will you do it? Or will you fail? Only time will tell. But you know two things: You will NEVER QUIT and that seed planted all those years ago by that book you read has grown into an unshakable belief system that drives every action you take. So to you… it is a forgone conclusion. YOU WILL DO IT.

    • Anonymous says

      Any advice on the best places to learn about paid media buying? Been reading everything I can find as well as trial and error on my own with my own $, but so much is contradictory it’s hard to know what to trust.

      • ReasonFromFirstPrinciples says

        Google “Finch Sells”. Read everything. Your answer is buried deep in there.

    • says

      When you are talking about paid media buying, are you talking mainly about AdWords & Facebook or also programmatic buying? I have a strong background in the first 2 (worked at Google in AdWords Sales for a while) but basically no nothing about programmatic. How important is it to master programmatic in order to scale an online business or is standard PPC (AW & FB) sufficient? Any resources or platforms you recommended for programmatic beginners? Thanks!

  24. David says

    This question is for the wallstreet playboys or anybody who would like to answer on the website. Once you become a millionaire and have a few million in your bank account, what are some of the best ways to preserve the wealth without letting inflation eat away your principal? and should you still dca into index funds/etfs? Thank you

      • Nixon says

        Agree completely. Worry about this when it is *actually* a problem for you. Otherwise this is just a hidden form of procrastination.

    • P says

      Recommend following simon black to learn how to avoid sovereign risk and counterparty risk with your bank. If truly fi

  25. David says

    TBH…It’s my current problem….I have $2 million in the bank and I’m 35 years old. I want to protect the principal however if I don’t invest, that money won’t last until 50 or beyond. Any suggestions?

    • Wall Street Playboys says

      Click free wealth management at the top of the page, sign up via the link and talk to a professional

      Done. We get so many questions we may as well open up some basic consulting services for a maximum of 2 hours a week to avoid the 100s of questions we get every day!

      In short, never bet what you can’t afford to lose. Your passive income needed to cover cost of living is = to your low risk bond exposure.

  26. says

    WSPs are a godsend.

    I feel the pain that “Extreme Entrepreneur” feels. I’m definitely a later starter.

    My parents had no clue what they were doing and I had no positive role models growing up. Took two years off after high school to do blue collar work, then graduated from college with a liberal arts degree at 24. Economy was shit, so I did one a year Americorps program to get connections and something on my resume after graduation.

    After Americorps ended I was lucky enough to talk myself into a B2C outside sales role at a large corporation (base salary, company car, brand that you would recognize). It was an excellent opportunity (and boy did I thank my lucky stars) for about a year, then management ran the company into the ground. Struggled for another 8 months, hoping that things would go back to normal. Nope. Got laid off the month before I could claim $10,000 in commission (if the company wasn’t going down the shitter, I would have grossed 70-80k this year. Instead I earned about 50K in a 8 month period).

    Sidenote: If your employer starts to falter, leave ASAP. Companies on a bankruptcy death spiral are like rabid animals backed into corners. Your loyalty WILL NOT be rewarded.

    Took a step back to re-evaluate. Realized that these 90k outside sales roles that I was qualified for A) are full of retards and B) cap out at about 150, with no meaningful potential for vertical or lateral movement. Who wants to be a manager at a B2C solar or window and roofing company?

    Now I’m taking some more short term pain for long term gain. Taking a paycut and a demotion by accepting a role as an SDR to get into software sales. Enterprise software is so much more complex than B2C that they make anyone with less than a decade’s experience start from the bottom. My OTE is only 60k, but I’ll probably be promoted to AE in a year max and have great income potential after that. Also just lined up my first $1,000 worth of work copyrighting on Upwork, so I should be able to pull in an extra 10-15k from that.

    It sucks now to realize that I wasted time and that I am taking two steps forward, one step back, but without WSPs I would be completely lost. Worst case scenario I can have a great time through the rest of my twenties and throughout my thirties. I might not be able to hit 1-2 milli by 35 like lots of the guys here have, but I can definitely hit it by 40. And who knows? Might end up getting an MBA to go into tech Ibanking 😉 (just have to run the math.)

    Thanks Wall Street Playboys!

    TL;DR. If you fuck up and graduate with a Liberal Arts Degree and find yourself in a low paying job like teaching, operations, or operations, you can still pivot to sales. Don’t get a shitty B2C job though, do whatever it takes to get hired as a BDR/SDR for a tech startup. It will be 1-2 years of lower pay, then incredible income potential.

    And learn copy or programming and get on Upwork!

  27. anonymous says

    I’m 35 and I messed up. Coder, income 115k + bonus, net worth ~200k, no side business. I made a site that generates $5/mo, yuck. Still going to buy efficiency.

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