Home » Interviews » “Don’t Quit, Get Laid!” – Leaving Wall Street for Blogging with Sam from Financial Samurai [TDI042]

“Don’t Quit, Get Laid!” – Leaving Wall Street for Blogging with Sam from Financial Samurai [TDI042]


Note (7/8/14): This interview was originally published on 3/10/14. This week, we’re going to feature some of my favorite interviews that were published when The Daily Interview was brand new, that many of you may have missed. As I’m busy packing and getting ready to move to a new home later this month, I’ve decided to take another week off from posting new interviews. Don’t worry though – we’ll be back with new interviews starting next Monday. In the mean time, enjoy this one! 🙂

There are few people I admire more than Sam Dogen, the mastermind behind the blog Financial Samurai.

I love a great entrepreneurial story, but I especially love when it involves leaving behind a very successful career to pursue a genuine passion.  In Sam’s case, he worked on Wall Street for 13 years before his passion for blogging (and doing other projects on his own) pushed him to want to leave his job (in addition to feeling burned out).

Here’s where things got interesting: He didn’t quit. He engineered a layoff that basically allowed him to get paid a six-figure sum in the form of a severance package.

Even better, his blog has been a massive success (his writing is very interesting, especially if you’re into personal finance), and I think it still has room to grow.

You can read the interview to find out the rest of his story.

Sam, I’m a huge fan of your blog – Financial Samurai – and the community you’ve built with Yakezie. It’s a remarkable success story that I know stems from your background in finance, and you’ve come a long way since your time in Corporate America.

Tell us a bit about your background and journey – where did your career begin? How did you ultimately leave your job behind and make the transition into blogging and essentially work for yourself?

Hi Eric, thanks for the kind words. Congrats to your new site launch! My journey began in 1999 when I joined Goldman Sachs in the Equities department in NYC. It was a dream come true given I got hooked on trading stocks my junior year of college. Working on Wall Street was intense. The industry pushes you to your limits in terms of endurance, patience and problem solving abilities. Something was always happening somewhere in the world.

Finance is a very cyclical business as anybody whose been investing over the past 20 years can attest. When the markets are booming, everybody feels wonderful because clients are making money, your firm is making money, and you’re making money. It’s when downturns happen where suddenly everybody asks, “What have you done for me lately?” Losing money and dealing with short fuses is not a fun time.

I always wanted to work until age 40 (2017), but I didn’t anticipate how fun blogging would be.

Financial Samurai started in 2009 during the middle of the financial crisis to help me make sense of everything. It was as if I was building a support group to help my own melancholy. It turns out a ton of people felt quite troubled by the downturn and a robust community of readers was born. By 2011, I started burning out from work after 12 years of doing the same thing. Working on Wall St. was no longer fun anymore. We were public enemy number one even though 99% of us had nothing to do with the housing crisis.

I’ve always wanted to do something entrepreneurial since graduating from college and I figured if I could negotiate a severance package, I would take the leap of faith and focus on my online properties. It took a year of planning, but in the spring of 2012 I finally engineered my layoff. Thankfully, things have worked out fine since.

What has been your greatest success (or successes) so far with your online business?

Survival has been my greatest success so far. There have been tons of land mines since Google started aggressively updating their algorithms three plus years ago and I’ve seen a ton of blogs disappear as a result. Sometimes it really feels like we’re dealing with a moody boss out there who can crush you one day or bring you glory the next day.

Besides Google, it’s tough to stay consistent writing three to four, 1,200-2,500 word posts a week. So many times I want to kick back and slack off for months on end given I already spent 13 years saving and investing 50%+ of my after tax income in order to generate a six figure passive income stream. “What’s the point of trying so hard?” I often ask myself.

The first reason is that I publicly stated my goal to generate $200,000 a year in passive income five years after leaving my job. The main reason is that I feel guilty for not maximizing opportunity and working hard every day because there are millions of people around the world who would kill for the opportunity. Growing up in developing countries really puts a number on you because you see so much poverty and suffering. America is almost like a cake walk compared to so many other places. I don’t want to take my luck for granted.

I believe in small wins to keep motivation and hope alive.

We all know that the odds are against us in everything we do, so to encourage myself and others to continue I created the Yakezie Challenge. The Yakezie Challenge is predicated on the Alexa Ranking system. If a blogger can get to 200,000 or below within 6 months and develop a great rapport with at least 25 other bloggers in the network, they succeed! What’s happened is that far more bloggers have succeeded and kept on going as a result.

I’m very proud to have started something to help motivate people to become better bloggers. Many have gone off to become full-time bloggers, work less hours, spend more time with their family, and travel because of the Challenge.

Blogging is a hobby that fills me with excitement every time I start writing a post. It’s very gratifying to publish a finished product and watch it grow up in the internet or fail. From the monetization of content through the wine pairing strategy, to creating your own products, to getting featured in major media organizations, everything is so much fun. Just when you think you can’t grow more, you do.

I never thought I’d break 100,000 pageviews a month until I did one day a couple years ago. I then thought there was no way I would break 250,000 pageviews a month, and then it happened in early 2013. Now I’m thinking how could Financial Samurai possibly get to 500,000 a month, and I’m only 40,000 pageviews away now. I fully expect the traffic to ebb and flow with the year, but perhaps maybe, my main site will continue to grow.

There’s a great Chinese saying, “If the direction is correct, sooner or later you will get there.

You’ve done a fair amount of writing regarding how to break free of a traditional job, including how to engineer your own layoff (a topic on which you wrote a book). What are a few mistakes people typically make when they are trying to leave a job and venture into self-employment?

The biggest mistake I see is people quitting their jobs and leaving tons of money on the table.

It is every employer’s dream to have an employee quit because the employer then doesn’t have to pay for COBRA, unemployment, severance, and deferred compensation. Based on all my interviews with people who’ve quit or who want to engineer their layoff, the biggest reason why they quit is FEAR. Employees are afraid of talking to their bosses and HR personnel to find a better way. Employees feel it’s a David vs. Goliath scenario with teams of lawyers ready to crush you for stepping out of line.

I empower employees with knowledge so they no longer have to be afraid of negotiating a severance package to do something more meaningful with their lives. In fact, I’m partnering up with some of San Francisco’s most successful employment lawyers to have them provide my book as a value-added offering to their clients.

I was able to negotiate a multiple six-figure severance package equal to over six years worth of living expenses based on existing spending habits. With such a buffer, I was no longer afraid to leave my job of 11 years and travel around the world for 12 weeks a year and build my online business at the same time. Partly due to the lack of stress to make money, I’ve been able to develop Financial Samurai much more naturally instead of filling the site with sponsored posts, and product review posts.

The book, “How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye,” has been a nice source of passive income to the tune of roughly $1,500 a month. I believe there is a huge opportunity to market the book more aggressively because there are so many books out there on how to get a job, how to get promoted, how to become a CEO and so forth. But there is no book out there which teaches you how to profitably leave your job.

The book has also helped me garner several personal finance consulting clients every month as well. This extra income is considered bonus income which gives me that much more breathing room to never have to work at a job again if I don’t want to. None of the income would have happened if I didn’t put in the effort, so that’s quite rewarding.

Let’s take a step back and look more generally at leaving a corporate job to pursue your own business: If you had to take your best advice or inspirational thought and put it into one sentence or phrase, what would that be?

Don’t quit, get laid! [Click here to tweet this]


My #1 motto for every single worker out there.

I’ve put together a post entitled, “When Should I Quit My Job And Do Something On My Own,” to answer your question more thoroughly.

Shifting gears to blogging: You’ve built a successful personal finance blog, which is something that isn’t all-too-common in this wildly competitive niche. What do you attribute your success to? Certainly working hard and being persistent have something to do with it, but is there anything else you’ve done to really stand out?

I think it’s very important to “own” your content. It makes no sense to read a post about how to retire if the person writing the post is 28 years old and isn’t retired. The same thing goes for reading a post about how to make six figures if the post is written by a freelance journalist who is making less than $40,000 a year. There’s too much fantastic content on the internet to write fluff pieces filled with pontification. Search makes finding content written by someone who knows what he or she is talking about extremely simple nowadays.

I encourage everyone to highlight three subjects where they have or think they have expertise and focus on producing content demonstrating their expertise.

My interests are in:

1) real estate, as a multi-property owner for the past 11 years;

2) investing, as someone who started in 1995 and spent a 13 year career in equities; and

3) career, as someone who got promoted to Vice President at 27, and then wrote a book on negotiating a severance package.

I also write a lot about early retirement strategies and financial planning. But with only two years of “retirement” under my belt, I’m not sure if I can say I’m an expert at writing about retirement life. I did pen a pretty popular post entitled, “What Does Early Retirement Feel Like?” to capture the emotions after a year in. But I changed the narrative around to discuss what it feels like to be financially independent, instead. Financial independence is what it’s all about.

Finally, it helps to be a big fan of blogging. Before starting Financial Samurai I was an avid blog reader and commenter. Even today with all that’s going on I still try and visit as many blogs as I can to interact with the author because it’s so much fun. I think because I’m happy to write for free, which is exactly what I did for the first year, I’ve been able to write more naturally.

If I do recommend a product, readers will have more trust in me as a result since I do so very infrequently. You can certainly try and make money by writing soulless affiliate product review posts after product review posts. But I think your readership will eventually burn out nor will you get much traffic from search because chances are high your review posts are not unique. I’m not comfortable recommending products that I do not use. It’s much better to show users how you use the knives instead.

What advice would you give to someone who wants to create a blog in a competitive niche TODAY? What do you wish someone told you about when you first started?

When you first start out, you are nobody online so you’ve got to give all you can. Always have the mindset of thinking how you can selflessly help someone else first. That’s the Yakezie Network motto. Of course being selfless is extremely difficult to do, but it is something I think we should all strive for.

Join a challenge like the Yakezie Challenge (Note from The Daily Interview: I’m a part of the Yakezie challenge!). Join a mastermind group. Go to your favorite sites and ask how you can help them.

It’s worth trying to come up with truly unique content because practically everything has been said before. The 1/10th Rule For Car Buying is something that really took off for example. Spending no more than 10% of your gross income on the value of a car is a simple, but effective way to blow yourself up. The TITTS ratio is another fun idea I proposed which gives readers a target for how much to save based on how much taxes they are paying.

If you can invent new terminology and help people remember an easy way to save or make people more money in the personal finance space, I think you’ll do very well.

What are your favorite online resources? 

My favorite online resource is Personal Capital. I’ve used their product since 2012 and recommend their free financial tools to my readers in order to track their net worth, make sure their investments are balanced, and minimize their portfolio management fees. Before Personal Capital, I had to log on to six different financial institutions to track 28 different accounts. Now I can see all my finances in one place and adjust positions accordingly.

I’m such a fan of Personal Capital that I decided to work for them on a part-time basis for three months. It’s been a blast helping them build out their Daily Capital blog and share my online marketing strategies with them. Most of all, it’s great to have some more human interaction again. Working from home definitely gets lonely after a while.

Finally, where can people find you online? 

You can find me always responding to comments on www.financialsamurai.com and on Twitter @Financialsamura. You’ll notice I don’t have an “i” and that’s because when I first set up my account I didn’t realize there was a space limit.  I’ve been too lazy to change ever since!

Thanks so much Sam for doing this in-depth interview with me today.

What do you think of Sam’s story? Have you ever considered “engineering” your own layoff? Leave a comment below!

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  1. I’m a big fan of Sam’s blog and he’s stopped by ours on several occasions. Love his story – thanks for sharing!

  2. Sam is the man! Love your 1/10th rule for cars. Keep up the good work and educating us folks 🙂

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