I remember going to Airbnb's Friday afternoon happy hour back in 2012. My college buddy's wife worked as an assistant chef and invited me over.
The office wasn't very large and Joe Gebbia, one of the founders, was horsing around with a wig held together by a white headband. After speaking to Joe for about five minutes, I decided Airbnb was a great place to work. I applied for some random finance manager job, and got rejected. Undeterred, I proceeded to apply to three other Airbnb positions because I strongly believed it was going places. No luck.
To put things in perspective, in 2012, I had just left my corporate banking job of 11 years (13 years total with two firms). My severance took care of my living expenses and I was making a livable income stream from Financial Samurai. All I wanted was to try new things and joining a tech company in San Francisco seemed like the logical next step. I had no tech skills, so I knew I had to take a step down in pay just to get my foot in the door.
If I got the job, I'd be a relatively rich man now because back in 2012, Airbnb was worth $2.5 billion. Now, Airbnb is worth somewhere around $30 billion, and Joe alone is worth close to $4 billion! Realistically, I would have probably earned a modest (for SF) ~$100,000 a year salary and received a standard $100,000 – $150,000 option package that would now be worth $1,000,000 – $1,500,000. Not bad when the company finally goes public.
Since my Airbnb rejection, I've applied to around 200 Bay Area tech jobs. Company names include Google, Apple, Facebook, and Uber. I even applied to a dozen Series Seed and Series A startups. None of them were ever the right fit. Although I've done stints as a consultant for three fintech startups, I've never once been offered a full-time job.
It's one thing not being able to find a job during a recession. But can you imagine going for five years during a bull market, spending a hundred hours applying and interviewing with companies and never succeeding in getting one of them to love you enough? You start questioning what's wrong with you. Granted, I probably didn't show as much enthusiasm as a regular job hunter, but still.
Accepting reality is a tough cockroach to swallow. But facing reality is what we must all do to survive and improve as people. Don't give up. Keep searching for the right fit. If somebody doesn't believe you're good enough, try to understand why and consider creating your own destiny instead.

Related: Career Advice For Those Interested In Joining A Startup
A New Job Awaits
As luck would have it, I got an e-mail from a tennis club buddy of mine whom I've been playing doubles with for the past five years. He said there was an opening at his son's high school for an Assistant Varsity Tennis Coach and wondered whether I was interested.
What's nuts is that I had just written about how I should become a USPTA certified tennis instructor to see if I can add value as an assistant tennis coach at one of the private grade schools in Honolulu in order to increase the chances of my unborn child getting in. Ever since I lived in Manhattan in 1999, I've heard so many war stories about how admissions is simply impossible at the grade school level.
I can't expect my child to be smart, talented, and hard working. But I do expect to do my best to help my child get the best education possible. One way to improve my child's chances of getting into a school is to see if I can add value to the school in the field of writing, online media, online entrepreneurship, or tennis since I can't compete with most families on money.
Eager to learn more about this new opportunity, I followed up with my friend's referral and applied. After a two-hour long interview with the Athletic Director and the team's co-captains, I got a phone call the very next day with the job offer! My work entails coaching the singles players, providing strategic advice during a match, and instilling in them a FIRE to never quit due to a lack of effort.
They can lose to a more skilled opponent who is bigger, stronger, and faster. But they will not lose because they didn't drill enough cross court backhands or hit enough serves.
Why I Accepted The Job
Assistant coaching pay isn't lucrative – about $5,500 over a three month season that entails 1.5 hours of practice each day, travel time, and team matches that may last as long as three hours. But, I'm not doing this for the money. I'm doing this because:
1) I love tennis – everything from playing, to watching, to figuring out strategy. I'm a guy who went to the U.S. Open alone one year and watched tennis from 11am to 11pm for four days straight. I spent $800 for one second round French Open ticket, and $1,200 for one second round Wimbledon ticket to fulfill my bucket list of seeing both Rafael Nadal and Roger Federer play on center court before they retire. I've played three times a week for the past eight years and won't stop until my knees break or my shoulder falls off, whichever comes first!
2) Help make a difference in a young person's life. Playing a sport teaches a kid how to work hard, compete, adapt, lose graciously, and win humbly. These are key attributes for success in any professional endeavor. I want to be there to help kids grow up to be awesome members of society. Everything starts with how we nurture our youth. One of my 2017 goals is to “really make a difference in 12 people's lives.” I originally measured this goal by the number of out-of-the-blue e-mails or comments I'll receive from readers telling me that so-and-so article really helped them be happier or financially more secure. With 12-14 members on the varsity boys tennis squad, maybe I can now make an impact with at least three or four of the players!

3) See what it's like to have a teenager. I'm a preparer, mostly because I realized long ago that I know very little about how to do anything I've never done before. The key to never saying, “if I knew then what I know now” is to simply seek advice from someone who's been there. When I write about having kids or getting an umbrella policy if you have a teenager, I'm pontificating. By coaching these young men, I'll get a better idea of how teenagers think and how I can be a better mentor and parent in the future.
4) Decide whether private grade school is really worth it. I'm a big proponent of public school, having gone to public high school (McLean), public college (William & Mary), and public graduate school (Berkeley) after spending the first 13 years in international private schools. But I've come to the conclusion that if you can afford private grade school (gross income = at least 5X annual tuition), you might as well send your kids to private, despite everything being free online. I want to see with my own eyes the value of private school now as an adult, by the way they teach their kids. I've already read all their course catalogs, college placement statistics, and taken a tour of the campus. The tuition for this SF-based high school is $48,150 a year, which makes the Hawaiian private schools at $20,700 seem like a bargain!
5) Build a network. Relationships are everything. People simply want to do business with people they know and like. I would never have been considered for this job if I didn't hang out with the University of San Francisco's head men's tennis coach for hours at a tennis tournament one day. We just bumped into each other one Wednesday and he observed my enthusiasm for the game as we got to talking about everything tennis. The USF head tennis coach happened to be giving my doubles buddy a lesson recently, and my buddy asked if the coach knew anybody who would be interested in the high school varsity assistant tennis coaching job. Both men knew the Athletic Director at the high school and recommended me. Of course I still had to interview, but it helps when you have strong referrals.
The other cool aspect of this job is that I get to meet the ~60 other coaches who work at the school. It's a completely different world from the financiers, rideshare drivers, startup workers, and online media friends I know. I'm excited to learn from veteran coaches and hear their stories. Just like that, I'm part of this great organization which has produced wonderful alumni for several decades. Perhaps there will be great insights I can share with all of you in the future as well.
6) Enhance a resume. I'm never too proud to start at the bottom and work my way up. And if you are too proud, please read: Spoiled Or Clueless? Work A Minimum Wage Job. Let's say I do a good job as an assistant coach for the next three years. Maybe I'll be considered for a head coaching position one day from this school or another school. Or maybe by then, I'll have a pre-schooler and we'll want to move back to Honolulu to be closer to family. Perhaps Punahou or ‘Iolani might think I can add value to their tennis programs given my CPR training, concussion training, and three years of varsity tennis coaching experience plus 30 years of playing experience. With such value-added services, perhaps my kid may have an easier time getting in.
7) An incentive to stay in shape. A main goal for everyone who has achieved financial independence is to try and stay as fit as possible. To die young after building enough passive income to permanently pay for life would be a crying shame. Having a job that makes me run around the tennis court and be surrounded by athletes is very motivating to stay healthy.
8) Experience new challenges. There's a fun saying, “If you're coasting, you're going downhill.” I'm determined to build Financial Samurai for two more years so that I can have 10 years of entrepreneurial online media experience under my belt. After that, who knows. But I've found myself faltering in entrepreneurial intensity ever since I took a month long tour to Asia in 2015. So many people were happy with so much less, the trip reminded me to focus beyond online traffic and revenue.
I am admittedly nervous about my first day on the job. It feels exactly like the first day of school. I hope the kids like me. And I hope we can have lots of fun!
Think Near And Far
Steve Jobs said, “You can't connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path.”
When I look back on my life, it's crazy how so many things happened without my anticipation. For example, by getting waitlisted at UVA, I never would have met my wife whom I met in Japanese 101 class at William & Mary. I couldn't imagine my life without her! She got into UVA and thank goodness, decided not to go.
If my net worth hadn't gotten slaughtered during the financial crisis, I never would have started Financial Samurai and left the corporate world in 2012. I'm also so thankful that in 2011 I was not promoted to Managing Director in 2011. Otherwise, I would have absolutely stayed on for at least five more years, if I didn't get laid off first.
The only consistent attributes I can think of that have helped all these years are:
- Work ethic – never fail due to a lack of effort.
- Always looking at the positives of failure.
- Adopting an unwavering belief that everything will turn out OK.
- Focusing on helping others first before asking for anything.
- Being mindful of the suffering of others.
- Showing gratitude.
Always think about how your actions today might affect you in the future. It's helpful to think in 5 or 10-year blocks. By thinking near and far, good things will eventually start happening.
Recommendation: If you're looking to leave a job to do something more meaningful, learn to engineer your layoff to get a severance instead of quitting. If you get laid off, you should get WARN Act pay, potentially a severance, unemployment benefits for up to 26 weeks, and COBRA healthcare. If you quit, you get nothing.
Update 2019: We got to the finals of the NCS conference in 2017 and lost to a school three times bigger than us. It was the farthest our school had ever gone. In 2018, we won our conference, got to the 2018 finals and won 4-3 against the team that beat us! Now it’s time to defend our title.
Sam, I bet in vast majority of those places that you didn’t get the job is because they knew you didn’t really “need” it. I assume most employers are looking for people that need the money, need to work and therefore will stay with the company. In this case perhaps financial independence works to your detriment?
Yeah, it’s definitely one of the reasons why I couldn’t get hired. I wrote about one experience here: https://www.financialsamurai.com/how-to-get-hired-if-you-are-overqualified-too-old-or-dont-need-the-money/
What’s the latest with you? Did you change your website?
Been focused on my SaaS company and a few other businesses. Still have my blog, but changed the URL to shorten it down – upfuel.com is the URL now.
Will be messaging you sometime soon for podcast invite.
We should sync up sometime soon :)
Nice man, congrats! Sounds like a dream fit for sure :) If you ever need a quick way to impress any of them, just challenge me to a match and I’ll allow you to whip me in front of everyone. Without breaking a sweat. (I literally don’t even know how to play tennis, haha…)
Cool! If you don’t know how to play tennis, what we’d do is called a LESSON! My usual tennis hourly rate is $85, but for blogging friends, I’ll cut it in half!
Hi Sam!
Great story — I’m glad that you’re getting the opportunity to coach and make an impact on kids. In my opinion, there’s nothing better. As I read your story, I reflected on how I would love to have the ability and freedom to be able to work a full-time job teaching/coaching. Unfortunately, a job like that just won’t pay the bills at this stage in life, so I’ll continue to enjoy volunteer coaching my kids for now.
I think you have the right mindset on coaching. I’ve coached both swimming and soccer over the years, and if nothing’s clear it’s that kids will amaze you with what they can achieve. It’s a bit of an art to figure out when and how hard you need to push them, but when you do it right the results are magical to see. Good luck, have patience, and enjoy the awesome opportunity to mold tomorrow’s leaders!
Sam, that’s great news about your new coaching position! Enjoy the amazing connection you GET to have with those awesome kids. I’m back teaching tennis as well and what a privilege it is. Be in touch!
Congratulations Sam and Aloha! Sounds like it’ll be a fun gig for you as you already enjoy playing tennis!
Maybe we can meet up and grab a beer someday as I’m usually out in Hawaii for work.
You’re going to be great and have a lot of fun, Sam!
Congrats Sam! This is big news and I’m sure you will excel at this position. This is what early retirement is really about. Being able to work at a job for the joy it brings you and not worrying about the money.
Congratulations! I’d love to hear more about your discussion process with your family on moving to Hawaii – was it an easy yes from everyone, and if not, how did you convince them? Are you going to buy more real estate in Hawaii now?
Thanks, but I haven’t moved to Hawaii yet. The coaching job is in SF. I was just pointing out that I wrote about coaching at a Honolulu private school one day, and how crazy it is that within a month of writing the article, here I am being able to coach for a SF private school to build my resume to further my chance to coach in Honolulu one day!
The conversation will be easy because my wife is totally on board. We LOVE Hawaii. It’s one of the reasons why we bought our house facing the ocean and built a resort-like living space to remind us / or pretend that we are living in Hawaii.
FS, two books, one on winning and the other on resilience in the face of losing and challenges. FS, every match involves a loser. Winning is something you can’t fake. Supporting the Head Coach’s vision and style, while helping the players handle and apply the lessons of losing, might be the two biggest challenges that surprise you.
”If I’m the Better Player, Why Can’t I Win?” by Dr. Alan Fox, PhD, who was Brad Gilbert’s coach at Pepperdine. Amazing sports psychology tips for winning at the top level, from both player and coaching perspectives.
”Playing From The Heart” by NCAA Div 1 player and professional motivational speaker Roger Crawford.
Whatever it takes to play at USF is one thing, but Coaching at that level is remarkable. Hope you can persuade him to feed you some wisdom, as you face your new duty. High-school level is a sticky wicket; the best players are usually the doubles teams. That way, all you have to do is win one-of-four singles matches. You may get player/coach/parental pressure to stack the lineup for a team victory at the expense of individual victories.
You are gonna be GREAT!
Gracias! Let me start off with Winning Ugly by Brad Gilbert first, and then see if my students actually read what I ask them to do, before moving on to more books. It’s raining cats and dogs here in SF, so we haven’t gone out to practice yet.
Just finished a 7 hour Coaching Certificate module online. So much to do and learn!
I’m ready for all the nuances coaching has to offer. Bring it on! :)
Sounds like a sweet gig! I don’t think the coaches at the public school I attended got paid much of anything, so it’s nice that you will get a little something.
As a former basketball coach on different levels, I can tell you that it will be a lot of fun. Also don’t fool yourself with that 1.5 hour stuff, it’s going to be a multiple of 3x at least. Happy for you and enjoy finding out about the “teenage life” again haha!
I have a feeling you are right! But so long as I’m having fun, I don’t mind. I generally always put in more that what is asked of me. It’s a great way to improve your chances of staying long term employed :)
Sam,
What positions were you interviewing for? I suspect that perhaps you didn’t really want the job or lacked some type of slave obedience and that’s why you didn’t get it? I’m just curious because either they didn’t need a finance personal whatsoever or you were interviewing for programming positions or something. There are actually tons of loan/finance companies out now which definitely need your help. Great post.
Rob
I applied for everything ranging from finance jobs, to content jobs, to business development roles, to digital marketing positions.
So I guess the rejections that baffles me the most are the ones in the content marketing and digital marketing roles. Here I am, someone who built a relatively highly trafficked site with over 1 million page views a month organically, who has an engaging community, and an enduring brand in the personal finance space who couldn’t even get an interview or past the first round.
Yes, I admit that my heart wasn’t really, really into going back to work full-time because of my passive income streams and my income streams. But I would’ve thought that a company would think that my background would be a no-brainer for them to build their brand online and give me a good pay package. I can remember four companies looking for roles I’d be perfect at taking on, and all four companies are now out of business. So, who knows if it was a chicken or the egg kind of thing, but they definitely did not successfully build a brand online.
Here are the reasons why I was probably rejected:
* CEO thinking “why the hell would he want to work for us when he is already financially independent?” See more: How To Get Hired If You Are Overqualified
* Fear of me leaving after only one year because of the job function. “Why would you ever stay? If I were you, I’d just go travel and have fun,” said several CEO. I told him I worked on FS for 7 years at the time and my previous firm for 11 years.
* Why would I do my best to work for a company for 1/30th or less the equity when I have 100% equity in my own company
* Not being able to convincingly fake a hunger to work for them (I really don’t like micromanagers, 15 hour work days, and commuting anymore)
* Not caring enough to put together a thick presentation for the health insurance startup with a misogynist founder. 10 pages versus 54 pages by another hire.
* Not qualified, not smart enough, couldn’t demonstrate my work ethic well enough, etc.
* Perhaps age? I’m 40 this year and have written about ageism before. Lots of the founders are younger and poorer and would rather work with folks more similar to them.
* A lot of it is consistent disbelief I’d ever want to get back in the grind b/c so many have told me what I’m doing now is exactly what they’d want to do AFTER an exit. Funny how the grass is always greener right?
The reality is this: if I was good enough, I would have been hired. Given I wasn’t hired, I wasn’t good enough. Hence, I’ve got to WORK on improving my communication, tech, writing, negotiation, presentation skills and MORE.
I hope other people who’ve been through a lot of rejection do a deep dive into why they were rejected in order to get better as well.
Sam
You’re definitely a unique candidate because most people who work in the bay can’t afford to not work. Employers want someone they can push around and they will try to keep them loyal and dependent enough to never leave under their own power. Personally, I feel that others should raise their head from the grid stone every once in a while to view the whole picture. I’ve had many rejections and I can tell you one thing about having so many. You tend to be mentally hurt less and less the more of them you get. It’s like “Oh, they needed this and they didn’t like me, Oh well” whereas my first rejection was mentally taxing. I was thinking “What did I say? Was it this?” I would go back and replay the interview in my mind over and over. I find now that I’ve had so many rejections, I’ve removed my emotions from the equation entirely. When I got to Silicon Valley after getting my grad degree I thought that people would be tripping over theirselves trying to hire me. It turns out they were indifferent. It was definitely a humbling experience and made me realize that college is very overrated in it’s effectiveness. In my opinion, I would prefer to make less and be free. Happy Monday.
Hi Sam – Throwing in a little advise here. You want to take a look on LinkedIn at what people’s profiles look like that have the job you want. See if they have a “type”. Used to recruit for marketers years ago, mostly looking for people that are already in house marketers at Fortune 500, or agencies that worked on large campaigns.
There’s also the issue with your work being a blog/personal website instead of with a company, no matter how successful your site is. Hiring managers want experience similar to their business, whether large company or start up, or industry specific. Hiring is a risk adverse undertaking, why take a risk when they can find someone that has been working for a competitor doing the exact same job with the exact same title, and o look, the exact keywords on the job description too. This is why transitioning to a new role is almost as hard as getting a first job.
Excellent tips! You should seriously write a guest post on FS about these job searching tips :) You’re like 60% of the way there already with these comments.
=). Think there’s enough info out there about the subject. Sifting through what is actually good information depends on where the person is, company/country culture, and the person’s perception. Google actually has youtube videos on how to interview with them as well.
For your enjoyment, here’s a blogpost I did about LinkedIn in 2013. Some things might be outdated with LinkedIn’s updates, but for the average job seeker most information is still relevant.
withdavidli.blogspot.com/2013/09/why-youre-not-showing-up-on-linkedin.html
Nice, next step is college tennis coach in Hawaii. My cousin taught the women’s team for a while. Dream job in dream location.
Very cool. I hope to join your relatives in 3-5 years time! It’s the master plan. I always had some kinda fantasy of being a tennis instructor at a 5-star resort in the Pacific. Of course the resort would provide me a nice suite with panoramic ocean views. One day! Gotta start somewhere.
Congrats Sam! I have no doubt you will have a positive impact on the team from Day 1. I hope you will keep a good data set and track everything like you do in all other aspects of your professional life so that you can provide us periodic updates of your team’s success.
Thanks for everything you do – world is definitely a better place with you in it.
-Coley
Congratulations on the new gig. Working with kids has much inherent goodness, most excellent for your karma. It is crazy (and perhaps just a little bit sad) how much it matters who you know and who knows you (this worked against you in your applications to tech jobs, and finally for you with this new job)!
Thanks! The world is so noisy now, who you know is almost a prerequisite now. Of course you still got to demonstrate your abilities, but to get your foot in the door often requires connections.
When I was hiring folks, we had a 3.5 out of 4.0 GPA minimum cut off. It’s not that we didn’t think someone with a 3.49 wasn’t qualified. It’s just that there were already SO MANY qualified people who had over 3.5! We can’t hire everyone so… we had to draw a line somewhere.
Congrats for your new job.
I’m still suprise that you haven’t been able to have a job related with finance considering all the knowledge that you have and shared on this subject with all of us.
Hope this new opportunity will open new opportunities in the future for you.
Good luck.
Congratulations! I hope you find coaching to be a rewarding experience, it definitely gives you an opportunity to make an impact! I’ve coached JV soccer for the past 12 seasons, and I love working with the players. I’ve also received many positive comments from parents thanking me for being a role model – they notice things that I don’t even think about. One of my favorite days each season is our alumni game, its great to see former players and find out what they are doing with there lives! Congrats again, and good luck!
Wow, 12 years is awesome! Great job. That would be nice if in 5 – 10 years an ex-player reached out to me as well. So cool. Very inspiring to hear about their journeys as they grow up to be men.
I too interviewed at airbnb a few years ago, but got rejected as well. At the very least, we tried our best to get into the company before ipo. There have been many opportunities these past 4-5 years, but many more companies which fail. The last company I worked for focused on mobile app gaming and went belly up (I should have seen that coming with all the saturation).
Happy that you found a job that provides a lot of benefit. I’ve been working in the Bay Area for the past 10 years and it’s hard not to get caught up in the modern day gold rush. I work at a super mega corp now and doing well with investments and saving, but living in the valley sure does make us sometimes feel like we are “behind” when in reality we are doing well.
A fellow reject. Awesome! In 2012, I still wasn’t 100% certain of permanently leaving the workforce since I had just left and that’s all I knew for 13 years. So my strategy was to simply identify every private company I thought was going somewhere and latch on. Too bad I had zero connections. But, I was also having too much fun writing my severance negotiation book at the time, playing lots of tennis during the middle of the day, and writing on Financial Samurai! So, it wasn’t all a failure.
Yes, once we remove ourselves from the Bay Area, it puts into perspective how good we have it, or how much farther our money will go.
I REALLY want to one day fully take advantage of the geo-arbitrage of living in cheaper Hawaii after selling my SF property. But, I need to wait for another bull cycle since everything is slowing now.
Congrats on the new job! Was trying for tennis jobs back when I finished college, more as a stringer working way up to a shop manger than coach though (definitely not skilled enough).
For the job applications. I’m surprised by the form rejection, this makes me think that you were cold applying instead of using referrals. As a recruiter, especially as one that works for a company that you listed, I can tell you that applicants get rejected all the time if their resumes aren’t near perfect (what the hiring managers want). Getting a referral increases your chances of at least getting a call.
For contractor to full time offers. Those are iffy especially for start ups. Never know how much runway they have left, though I guess if you worked on their finance you would know.
I’ve already commented previously about my thoughts on bigger pre-ipo companies like Uber. But working for these companies are different in the way stocks work. Are you committed to working for the company until they IPO? 5 years has passed since you applied to AirBNB. If you left before that, would you be okay paying taxes on $1M-1.5M due to increase in valuation, but have it as a non-liquid asset for the foreseeable future?
Yes, most of the ~200 applications were cold applying instead of using a referral. What I’d do is identify a company, say Google, and then search by SF, then all interesting job functions. Then I would apply away. Relatively easy to apply to, but very ineffective. Where I have received a freelance offer was based off a relationship or a competitor reaching out b/c they heard I provided such services.
I’d be OK paying taxes on my $100,000 – $150,000 grant if it’s worth $1M- $1.5M now, absolutely, even if the tax is based on a profit of $1M – $1.5M minus $100,000 – $150,000. Airbnb is the one company I’m pretty confident will be worth its private value when it goes public.
The alternative is to just keep on working for Airbnb until the liquidity event so I have the money to pay the tax. That’s what most people do. 5-7 years working for them isn’t that long. I spent 11 year at my previous firm,
If you go on the job search again. I would recommend using referrals as much as possible. If you don’t know someone at the company, find the same job title on LinkedIn and send an employee or manager a message. Learn more about the role and what you bring to the table. Never solely rely on a recruiter, which is what you’re doing when you apply to the position. Your application profile will be sitting there with the hundreds of others of people, and depending a recruiter who’s already swamped with work to be diligent. Vs a scenario where a hiring manager talks to the recruiter and goes “this guy reached out to me on LinkedIn, profile looks good, set him up with an interview”. Ramit Sethi has excellent posts about how to start a job search, and I mostly agree. Reach out to your network first , best ROI. For unknown people, start setting up lunch/dinner dates (always pays) to get to know them, what the role is, what they are actually looking for (job descriptions usually too vague). Treat this like an interview and get a referral. These steps are 10-100x harder than just applying online, but much more effective.
And 11 years.. wow. Didn’t realize. Used to recruit for the financial sector, managers won’t even look at people who didn’t stay at one company for 4-5 years. So different in the bay area. Most people switching jobs 1-2 years, if IPO or acquisition average 4 years to fully vest/retention bonus.
Good tips for folks to follow. I was courted by traditional financial firms that ironically paid much, much better than every single start up or private company that I applied for. But I wanted to do something new after 13 years of traditional finance.
My situation was not having tech network, waiting to build a tech network until utilizing them for a referral, or just applying with no relationships and not waiting for anybody. Because I don’t like to rely on anybody or use anybody for an intro, I just went directly to the company’s website and applied for the jobs that they were open.
Getting rejected so many times was not all bad. Each rejection give me a quote power up” try harder to build Financial Samurai. I really like to see projection when things are going a little too smoothly. By getting rejected so many times, it also gave me this, “back is against the wall, do or die” feeling, which I really, really enjoy. It’s thrilling to work when there is no safety net! Does anybody else feel this way?
Speaking of Ramit, how do you think he has been able to convince people on his job search techniques when he has never had a job? He is one of the people that inspired me to believe that anything is possible because he also wrote a book right after college on how to be rich when he had no money graduating. Anything is possible!
It’s great that this site worked out for you. Love the back against the wall feeling. After accomplishing the goal it’s like “i can’t believe i did all this. could i have done this all along?” reminds me of Peter Theil’s saying of imagining your 5-10 year plan, then asking yourself why you can’t do it in 6 months. Or Seth Godin’s advise on not waiting until you get all the ducks in a row.
For Ramit. He’s a psychology major, and really took it to heart in analyzing situations and mental scripts. The biggest fault I see with people, that Ramit smashes, is only having one perspective. That people only see how hard they’re trying, not understanding how the other side feels or has to deal with. Candidates think they put all this effort into writing a resume that hiring managers should take a few minutes reading it. As a recruiter I find this laughable. The Ladders did a study and found recruiters average 6 seconds per resume, and that’s mostly true for people that don’t get a call. Other times it’s likely not more than a minute.
The other critical thing that Ramit nails is the networking. The person to person connection that will give numerous advantages. Think about recruiting, you know someone on the team. Not only are you top of mind if you’re good, you get automatically notified to interview instead of having to look up roles periodically. Get information on what the role actually is versus the job description. In a mind set during the interviews that you have been thoroughly prepared.
As for him convincing people. He needed case studies. Prove that it works on a small group and use them as examples. He talks about how he and his classmates used to swap interview notes. Test out different ways of answering things. Think about this as consulting work. Do a few for free to build your portfolio, then leverage portfolio to prove you can do the work.
Note that one of the few things I disagree with him on is the salary negotiations. I’m one to advise naming your number first. Do the research and anchor at a higher number with market data. This would be near impossible decades ago, but there’s no excuses now unless you’re in a very niche field.
Congrats on the your coaching gig! Wow – that will be a different type of challenge. I had to laugh at #3 – “See what it’s like to have a teenager.” Teenagers are pretty much the opposite of preparers. On a positive note, your patience skills will likely advance a few levels, which is good for any kind of parenting. I raised 2 very…energetic…girls through their teenage years. I don’t think I’d sign up to do it again, but I certainly learned a lot, and they’ve turned into good young adults.
Because of your genuine desire to help other people succeed through sharing your knowledge and experiences, your investment in those kids will make a difference in their lives that you’ll find very rewarding – but it won’t be easy. In a previous lives, I trained teachers in L.A., taught English in Mexican Universities, taught robotics to kids in Washington, and tutored kids in all subjects near Microsoft outside Seattle. It was so awesome to help those folks achieve their goals and realize I was making a difference, often when I thought they were totally ignoring me. Patience, consistency, fairness, kindness.
I’ll never forget the afternoon I was having drinks in a bar with business associates when the guys across the table from me stopped talking and looked up over my head. I felt a tap on my right shoulder and turned to see a young man in his 20s I didn’t recognize. “Do you remember me?” he asked. I apologized, as I didn’t. He reminded me I’d tutored him in various subjects when he was starting high school, but what he remembered most was me listening to him as he tried to understand his parents’ divorce and the advice I gave him that helped guide him to constructive ways of dealing with it. “I just wanted to say thank you for changing my life,” he said. BOOM. That felt great.
That’s awesome! You’ll have a chance to make a huge difference for young lives. Really great. Enjoy your new job. It sounds like you will have a lot of fun.
Congrats Sam. It is amazing to be able to have the time to do this job. It is one of the benefits of early retirement (or in your case leaving the corporate world).
The dots definitely connect in strange ways. I never imagined living in the Bay Area (let alone Santa Rosa- I had never heard of it 14 months ago). Then I married my wife in Boston (that is where her family lived at the time and was from). We moved and thought we would be staying East of the Mississippi River for the rest of our lives. 6 months later her sister starts a tech company, moves out to San Francisco 2 years later, and then 6 years later here we are. That is just one example. There are many more I can trace back in my life.
This is one reason I always try to respect everyone (and I mean everyone) I meet with respect. You never know where or when you will meet them again or their friends.
-EJ
Those students are so lucky to have you in their lives for the seasons. I’ve had similar things land me a job. I still had to interview and be a good fit, but respected folks as my recommenders got me in the door.
Congratulations~! They are lucky to have you, Sam~!
Congrats on the new opportunity! Glad you found something that lets you combine your passion for sport and for helping kids. I always thought I would coach field hockey again at some point in my life if I was able to. I don’t really understand the draw of elite private schools though. I went to public schools for K-12 and then went to a prestigious private school for college. Some of my private school friends told stories of the underworld of elite private schools with the coke, sex, money, snobbery, and lack of parental supervision. I’ll take an old textbook in a public school over that any day for my future kids. Plus, I’m suspicious how much of a difference public vs private would make if you have an active parent who can provide learning opportunities outside of school.
I have the same thoughts, so I’m looking forward to witnessing the differences first hand. When you’re not part of an organization, it seems like there’s an easy tendency to view those within an organization as snobby or whatever. But I’ve found this hasn’t been the case once you get to know the folks.
How cool would it be to have an active teacher and coach to help provide more guidance? I’d love that as a future parent.
One thing that stood out for me is even thinking about wasting money on private schools. I would think that in most parts of the country, there are some parts of the metro area with good school districts. It would be a lot more beneficial using the money you spend on private schools for 12 years and spend it to live in a better school district.
Check out: Is Private Grade School K-12 Worth It?
Some have thought about the financial benefits of just investing that annual tuition for 14 years since grade K and giving the child the proceeds some time in the future. I have a feeling that folks who can afford $20K+ a year in tuition ALSO have these trusts set up for their kids as well.