The decade-long advice to “learn to code” is losing its edge. With tools like Claude Code handling the heavy lifting, a basic three-month online course may be all anyone needs to build what they can imagine.
The more important skill is investing. If you learn to invest, you can build lasting wealth and bypass the gatekeepers (college admissions, hiring managers, corporate ladders) on your own terms.
I’ve been learning to invest since 1995. My early tuition was losing thousands of dollars in stocks I didn’t understand. Blowing up a small portfolio is fine. The sooner you start investing real money, the faster you learn.
That skill has kept both my wife and me out of the workforce for over a decade. But I’m clear-eyed about it: since 2012, we’ve had only two down years (2018 and 2022), so much of the return comes down to luck and a sound asset allocationthat put us in position to benefit.
But a solo trip to Honolulu this spring to see my parents reminded me that learning to sell is just as vital. For many people, it could do even more to improve their lives than investing.
It doesn’t matter if you’re a CEO, a partner at a law firm, a bestselling author, or a janitor. You must sell to win business, stay employed, gain access, and find love. Those who can’t sell miss out on far more than those who can.
Here’s a small story where learning to sell could have changed our spring break.
Separate Trips
My wife took both kids to Virginia and West Virginia and left me behind in San Francisco. When she proposed the idea, I wasn’t enthused. The trip meant two flights to Charlottesville with a tight 50-minute connection, a random motel because her mother’s house couldn’t fit us all, a two-hour drive to see her father in a cabin in Sulphur Springs, West Virginia, and another two or three nights in a motel.
I wanted to be with my family, but not on that itinerary. I proposed flying her parents to San Francisco instead, but neither wanted to travel. So I passed, supported her in going, and used the time to see my own parents. Divide and conquer.
The Missing Sales Pitch
Looking back, if my wife had framed the trip differently, she could have sold me.
She could have branded it as the trip where it all began. Fly into Richmond, drive 40 minutes to the College of William and Mary where we first met, and walk our old dorm halls, hit the Commons cafeteria, eat baked spaghetti at Paul’s Deli, play frisbee in the Sunken Gardens, take pictures at the Wren Building.
The kids could learn history on Duke of Gloucester Street, visit Jamestown, and ride the coasters at Busch Gardens. Then drive to Charlottesville to see her mother, visit UVA and Monticello, and find a decent hotel. Then on to Sulphur Springs, where there’s apparently a cool cave and beautiful forest on her dad’s property.
The underlying logistics would have been more complicated, but the framing transforms an obligation into an adventure. I think I would have been sold.
That said, my wife also knew this wouldn’t be an easy trip for me given her parents’ situation. So she didn’t push, which was kind of her.
My Sales Pitch Is Easier
Selling her on Honolulu is easier because there’s a direct flight and it’s Hawaii.
That said, I still had work to do before the summer of 2025, because we’d all be under one roof with my parents. My dad is fine with it, but my mom really values her privacy and space. Sharing a kitchen, refrigerator, and washer and dryer were real pain points.
So I channeled that tension into remodeling a rundown two-bedroom, two-bathroom in-law unit over five weeks for about $41,000, including furniture. I hate remodeling, but I’m glad it’s done. Having that separate space is a genuine luxury.
I put in the work because I genuinely wanted her and the kids there with me. To sell the upcoming four-week summer trip, I:
- Reminded her we’d have a free two-bedroom, two-bathroom unit to ourselves, the equivalent of $1,500 to $2,000 a night in the resort area
- Showed her the weather forecast (a reliable 70 to 85 degrees)
- Highlighted three new restaurants plus our favorite poke spots and shaved ice places for the kids
- Lined up beach days, waterfall hikes, and afternoons where I’d take the kids solo so she could rest
- Talked about the value of the kids spending time with grandparents who have contributed significantly to their 529s
- Pointed out how repeated exposure to Honolulu’s people, environment, and culture would make any future school transfer easier
- Spent an agonizing amount of time proving our Hawaiian heritage for our children
- Told her how much I appreciated her years of coming to Hawaii to see my family
- Committed to handling all the driving and most of the activity planning
I’m probably more assertive than most when it comes to selling. But when you want something enough, that’s part of the job.
The Keys To Being a More Influential Seller
Selling is an acquired skill. It requires strong communication, a deep understanding of what the other person actually wants, and the ability to articulate a clear value proposition. Here are nine principles that have served me well:
1. Give first, ask later
If you ask first, your odds for receiving drop dramatically. If you give first, generously, without conditions, the other side feels compelled to reciprocate. Build up so many credits in your giving bank that people want to help you.
Cold emails that open with a request usually get ignored. Emails that mention a post that helped them, or note they left a positive book review and want to send a bottle of wine – those get a response practically every time.
2. Know and articulate your value proposition
Once you’ve established a giving reputation, you need to clearly communicate what you bring to the table before you ask. Don’t assume the other side knows.
I might invite a founder to play tennis at my club, pay their guest fee and drinks, and simply aim to make a new friend. Over time, if I want to invest in his company, I can offer to write about his company on Financial Samurai. That’s a concrete, differentiated value exchange, not just “I’d like in.”
3. Understand the other side’s pain points
You can’t sell what someone doesn’t want. The sharper the pain point, the more motivated the buyer.
At 34, my biggest pain point was not wanting to work another day at my investment banking job. I was burned out on the hours, the politics, the travel, and demanding clients. That frustration became the seed of my bestselling e-book, How To Engineer Your Layoff, now in its sixth edition.
I knew from Pew Research surveys that I wasn’t alone in my work suffering. Successfully negotiating my own severance, then my skeptical wife’s, gave me conviction the product worked. At the end of the day: who doesn’t want to leave a job they hate with money and a new lease on life?
4. Be an excellent listener
When you’re talking, you’re not listening. When you’re mentally drafting your response, you’re not listening either. An effective listener repeats back a piece of what the speaker said before responding. They nod their heads and look the speaker in the eye
When your four-year-old is mid-tantrum, don’t raise your voice. Crouch to their level. Listen. Then say, “You’re mad, mad, mad,” name the emotion, and then acknowledge the desire. That simple act of mirroring de-escalates faster than any command to “calm down.” Once they feel heard, they’ll follow your lead. Adults aren’t that different.
5. Create an aura of exclusivity
People want what they can’t have. The Rolex Stainless Steel Daytona is coveted not because of the watch itself, but because Rolex restricts its supply. You can’t walk in and buy one, you have to earn the allocation through repeat purchases.
Elite universities run the same playbook: a 5% acceptance rate makes an otherwise standard education feel transformative, even though the professor teach from the same textbooks.
If my wife had framed the Virginia trip as a one-time-only family journey back to where it all began, whether strictly true or not, I probably would have gone. I’m nostalgic. Scarcity makes you act.
6. Learn to walk away from everything
The best salespeople have a thick skin and an easy exit. Success is a numbers game. If you knew it took 100 rejections to get one yes, you’d stop treating each rejection as a setback and start treating it as progress.
The classic car dealership move works because it’s real: the moment you’re genuinely prepared to leave, the salesperson’s leverage collapses. Their only alternative to a thin-margin deal is no deal at all. The same principle applies in dating, real estate negotiation, and job offers. Desperation is the enemy of leverage.
7. Develop an unshakeable positive attitude
People buy from people they enjoy being around. Perma-pessimists close fewer sales, the same way perma-bears underperform in a market that rises 73% of years.
When AI companies began scraping Financial Samurai’s content without credit or compensation, I felt helpless for a couple of months. Then I reframed: if I can’t defend against it, I can at least profit from it. Aggressively investing in AI companies starting in early 2023 has turned out to be incredibly profitable so far.
Optimism isn’t naivety, it’s a competitive advantage that enables you to better find opportunity.
8. Follow through on every commitment, no matter how small
Nothing erodes trust faster than broken promises. If you tell someone you’ll add them to a group chat, add them. If you say you’ll send them a link, send it. Small follow-throughs compound into a reputation for reliability, and reliability is the foundation of any sale. Conversely, a pattern of small misses signals to the other side that your bigger promises are equally hollow.
I recently committed $100,000 to a first-time VC because I liked the guy and believed in the growth of cybersecurity. To entice me to invest, he made small networking promises such as a demo day invite and a group poker chat add-in where I already knew 80% of the people. Unfortunately, he followed through on neither, so I’m hesitant to invest in future funds he launches.
One reason long-time Financial Samurai readers keep coming back is reliability. Since 2009, I’ve published three times a week plus a weekend newsletter, without fail. The more consistent a product, the more willing people are to invest in it and recommend it to others. If something feels here today, gone tomorrow, you won’t risk your money or your reputation referring it.
9. Personalize your pitch
Generic pitches fail. The more specifically you can speak to someone’s individual situation, history, or aspirations, the more persuasive you are.
A pitch that could have been sent to anyone rarely compels anyone. Taylor your pitch by niching down to the details.
Don’t Let Financial Security Make You Complacent
One paradox of achieving FIRE is that confidence can quietly erode your willingness to sell yourself. You no longer feel the urgency. Requests from strangers start feeling like impositions. Effort that once felt natural starts feeling optional. You have f-you money, so why bother selling yourself to anyone? You’re free!
But freedom without intention can become isolation.
I’ve noticed my own enthusiasm for responding to every comment and email has waned, especially when there’s no warm greeting, just an ask. I’ve built a low tolerance for people who make no effort to establish a connection before making a request. And frankly, that’s a reasonable filter.
But it carries a real risk: the person whose email you ignored at 40 may be the person with leverage over an opportunity at 55. Money can open many doors. But it can’t buy genuine goodwill from someone who simply doesn’t like you.
Stay sharp on your sales skills through practice. And perhaps above all else, practice kindness. Don’t be like that arrogant real estate agent who treated my kids and I poorly because the market is hot.
As Toni Morrison once wrote, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
Questions for You:
- What’s the best or worst sales pitch you’ve ever received? What made it land or fall flat?
- Which of these principles do you struggle with most, and why?
- Have you ever lost a deal, a relationship, or an opportunity because you failed to sell the value proposition? What would you do differently?
- Do you think selling is a natural talent or a learnable skill. And has your opinion changed over time?
- For those who’ve achieved financial independence: have you noticed your drive to sell yourself or your ideas getting softer? How do you keep it sharp?
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Each month, I mail out signed copies of Millionaire Milestones for those who take advantage of Empower’s free financial check-up this year. You can read about my experience and the promotion instructions in this post. I’ve taken advantage of three free consultations with Empower over the past decade and each session has helped me better understand my finances.
Financial Samurai is a promoter of the Empower Advisory Group, LLC (“EAG”), and is not currently a client.
