Growing up in Chicago is about hard work. Everyone is working. I think it’s the weather in that it’s either rainy, windy, snowing, or overcast half the year. When the weather half the year sucks, you don’t have much to do but…work.

On top of everyone always working, there’s a cap to wealth in Chicago. Not a numerical ceiling, but a visual ceiling.

There are rarely G-Wagons driving around, most homes can only get so big in the narrow lots, and parties are usually at a restaurant or bar.

If you have a newish car and a single-family home, you’ve made it. You did it! You’re basically at the top in Chicago.

When I come back to Los Angeles, it’s easy to compare. The house someone else has, luxury sports cars, massive amounts of land, clothing, etc etc.

It’s such a trap as we all know someone who’s more well off, that looks up to someone else above him as the goal post.

I love Morgan Housel’s books and his principles of “don’t compare yourself to others”, etc, etc. It sounds good…

But what I’ve realized is that I think mentally, the comparisons stop when you’re at the top of your neighborhood. As in, within the nearest 10mi, you’re the crème of the crop lifestyle-wise.

That’s when a majority of the mental comparisons stop.

If you’ve figured it out without moving, drop a comment. Would love to hear.

Not all expenses are created equally.

Some expenses just have to be paid, and you move on. Things like property tax bills, utilities, car repairs. There’s not much return for those dollars spent. They’re 1:1 on the ROI scale.

Other expenses may have a 3:1 return. You get three times the joy for one dollar spent. That could be a watch to celebrate a big event, clothing, trying a new restaurant experience, or a new laptop.

They’re nice upgrades and you enjoy them, but they slowly become the norm and have less value overtime.

Lastly, some expenses have a 10:1 return. They have so much value, you couldn't care less about the money you spent and would do it again in a heartbeat.

I don’t mean to be cliche, as this is different for everyone. But for me, that’s been hosting friends and family.

My mom just retired after 5yrs of considering it. My brother and I rented out a restaurant for her closest family and friends, decorated it really nice, got a photographer, and got to spend a really great time together.

Another 10x return expense was renting a beachfront property to work and surf all day with close friends. For an extended weekend, being able to tell stories, sit and stare at the ocean, and surf all day is a memory that makes me happy when I think back.

Ramit Sethi, financial advisor influencer, says to find “Your Rich Life” and relentlessly cut off the rest. For post-exit folks, I think that’s a reminder to search for 10:1 expenses and shave the sub-optimal ones.

When you’ve sold your business and you’re financially free from having to generate income to sustain your spending, you must navigate your day-to-day life differently.

We’ve been trained to attend school, get a job, save money, and retire at 65. This model breaks when you’re financially independent earlier than 65. What if you’re 40 or 30? How do you spend your time now?

When you hit your financial goals, you experience Arrival Fallacy. It is “the mistaken belief that achieving a goal will lead to lasting happiness.”

I’ve used the template below to help re-point me in the right direction.

This template is great for folks who are within the first few years after selling their business. It will help you create a sense of what you want to spend time on, and “no boundaries”. As in, if opportunities arise that don’t fall within these new lanes, it’s a “no”.

It’s best to print this out and write it on paper first, allowing yourself to wonder. Revisit it every few months to see how you may want to change your responses.

The sole goal is to answer the question, “What’s the life you want?”

1. What makes you happy?

What does an ideal day look like for you that leaves you feeling relaxed, present, and excited for more?

When would you wake up, what would you do, and how would it make you feel?

You may not know yet, so feel free to stay high level

My Response

• 6:30am - Wake up

• 7:30am - Surf or gym

• 9am - Dog walk

• 9:30am - I feel most productive in the morning so complete important tasks (family tasks, house issues, email, finances, etc)

• 11:30am - Dog walk

• 12pm - Lunch

• 1pm - Read or other projects

• 4pm - Wife is home from work

• 6pm - Dinner

• 7pm - Family walk outside or unwind

2. What are the core principles you want to live by?

These are guardrails to help you make future decisions. They begin the create the things you want to dive deeper in, and other items to say “no” to.

Begin to question your responses. Ask “why” “how much?” and “when?” a lot. This helps you understand the specific responses and reasons behind your responses.

My Response

I want to be more present with my wife, family, and friends daily.

• Why? I haven’t been as present as possible, creating conflict in my marriage.

• Why? I want to focus less on what’s next, and more on enjoy what I have now.

• Why? I want to enjoy the time I have with my parents now vs always be on my phone or laptop. One present hour, is better than four hours sitting nearby but not engaged.

I want to improve my skill sets regarding hobbies and a future business.

• Why? I feel if I’m improving, I’m not stagnant and it creates a challenge for me

• Why? Helps create excitement when I feel I’m improving at something. The challenge is time balance with family life.

• Why? I enjoy reading business and self-improvement books.

Create a healthy lifestyle via marriage, food, and fitness.

• Why? It’s important to me to be in a 60/40 marriage. Continue to keep things fresh and surprising.

  • Why? Relationships can get stale over time if I don’t continually add value.

  • Why? Quality time makes her and I happy

  • How? Mentally be in a state of dating long-term. Experience new things together (bike rides, restaurants, locations, games)

    • Use social media less. Why? Instagram/X are very addicting with little to no value-add.

    • Use Do Not Disturb more. Why? Notifications are very addicting to check.

• Why fitness? I’ve seen people 60yrs+ who are virtually immobile. Sad way to live out your life and don’t want to be in that state.

  • How? Exercise 5x+ a week (run, surf, strength training). Maintain good cardio and strength exercises to be mobile for longer.

• Why food? US food quality isn’t great and eating more unprocessed foods make me feel better.

  • Why? Via Peter Attia’s practices, healthy eating helps reduce the 4 iceberg health issues (cancer, diabetes, dementia, heart disease)

  • How? Increase protein to 130g+ a day to be full and not crave snacks. Don’t eat til filling stuffed, 80% is perfect. Swap natural foods in for unprocessed options.

Keep life simple. Be very careful with adding possessions and more “weight” to our lives.

• Why? More things means more upkeep and less flexibility. We value flexibility.

• Why not? Buying certain things does feel good. Maybe it’s more of being particular. Can items over $1,000 have a “pause time”, wait one week before pulling the trigger?

• Why? It’s easy to say “yes” to opportunities, but these may add weight overtime. Ideally saying “no” more helps me with this core principle.

• How?

  • Keep finances/investments simplified. There is no need to add additional risk, you can be in conservation mode. Avoid the feeling of investment FOMO and stick to the plan.

  • Allow myself to not worry about illiquid investments. Losing money feels worse at this stage than the joy of additional gains. I don’t want to squander away such a powerful/lucky opportunity.

Spend time carefully. Spend time on things I’m passionate about or get positive energy after I complete them.

• Why?

  • It’s easy to say “yes” to meetings, coffee, consulting arrangements, etc.

  • Because I shouldn’t feel obligated to anything. It’s easy for me to have momentum and say “yes” to calls or meetings I’d rather not attend.

  • You always regret being involved, stop repeating the madness.

  • I don’t want to work 70hrs+ per week again

    • Or do I get naturally obsessed? Just don’t conflict with family is the goal.

    • Why? I end up getting an unhealthy addiction (reduced sleep, activity, stress, takes away from marriage).

  • ⁃ Why unhealthy? I sacrifice everything possible for the business to improve, sell, support, and grow

• How?

  • It’s okay to say “no”. The other person will understand respect your decision.

  • Think for a few minutes if this is something I’m excited about or if I’m just being nice.

  • Let myself build projects without expectations that can limit starting things. Treat the first success as luck.

    • Why? The fun gets sucked out when you think too much about future planning projects.

3. What are your financial goals?

Think about how you want to generate your income. Should that be actively or passively created?

What about spending? What do you want to spend and can that be covered in your new life?

Lastly, how will your portfolio be managed, and how much time do you want to spend managing it?

My Response

• Build and sell a software company for $100m

  • Why? This would beel like a powerful achievement and also give the ability to have higher annual spend through the 4% rule.

    • How? Grow a company to $20m ARR profitably could create a $100m valuation from a 5x multiple.

    • Why $100m? Why not $50m or $10m? $100m feels like a large achievement.

      • Why? Is this ego or a financial need?

      • Would your life be much different after sacrificing 10 years on this? No

      • What are you looking to have? Nothing

  • In conclusion, additional money plus violating family terms of not overworking isn’t the right direction. I’m striking this point.

• Be able to wake up every day and spend time doing things that get me excited. Not have to worry about working full-time to cover expenses.

  • Why? Financial flexibility feels like the crown jewel. Maintaining a reasonable spend gives long-term flexibility.

  • Why? Because we enjoy the freedom to plan our day with things that excite us vs what we have to.

• Work on an income-generating software product while balancing personal life/passions.

  • Why? I enjoy working on businesses that can help people and also generate income as a reward.

  • Is this the income-generating ego peaking through? A little. But it feels good to have active income vs passive.

    • Could the income generated by limited? I don’t think it’s limiting the income, but it's limiting the time spent on generating income.

• Live within our annual spending means.

  1. Why? I want to never need a job again, only if I want one.

  2. How? Have discipline on larger spending items. It isn’t the smaller day-to-day expenses, it’s the larger, one-off that through a budget off.

• Keep our portfolio allocation simple. 60% equities, 40% fixed income.

  • Why?

    • I don’t want to worry about investments that I don’t understand or worry about getting cash returned. This goes back to, “keep life simple.”

    • It creates considerable upside while generating tax-advantaged income for us to life on.

    • I want to reduce mental cycles around investments and less worry about money.

  • How? Utilize a financial advisor to manage the fixed income side and advice when needed.

• Be thankful for what I have; recognize what I don't have is “envy” and move on.

  1. Why? It’s easy to continue wanting more, which feels like a never-ending quest.

  2. Why, you could buy it anyway? I’d rather not continue acquiring things to maintain, especially if they don’t give me long-term joy.

• Don’t work 70hrs/wk or a crazy schedule again. Or do I get naturally obsessed? Just don’t let it conflict with family time.

  • Why? Ended up getting unhealthy (sleep, activity, stress, takes away from marriage)

  • Why unhealthy? I sacrifice everything possible for the business to improve, sell, support, and grow

4. What are your personal and family goals?

Separate from work, what are the goals you want to accomplish personally? How do you see yourself in a year?

How do you see your family going forward and what does life look like in regards to family?

My Response

• To continue having empathy and put in proactive effort into our marriage

  • Why?

    • Important to me to maintain our relationship and allow it to thrive

  • How?

    • My wife’s love languages are quality time together & gift giving. Excel there.

    • Plan 2x a week unique experiences together. (ex. bike riding, new coffee shop, tennis, weekend trip etc) to continue keeping things fresh.

    • Reduce phone usage at night and weekends. Utilize Do Not Disturb.

• Continue to improve surfing

  1. Why? I truly enjoy spending time in the water and always leave with positivity.

  2. How? Utilize weekly coaching.

• Lift weights 3x/week and run 1x/week

  • Why? Following Peter Attia’s optimal health program, I want to be mobile for as long as possible.

• Eat healthier through 130g+ of protein a day, reduce processed foods.

  • Why? Crappy foods will come back later in life to increase chances of heart disease and cancer.

• As we live further from family, fly to see them every 1-2mo

  • Why? Our parents won’t be around forever and we want to create memories with them to not have reg’t have regrets later about not spending enough time together.

• Annual trip with college friends

  • Why? It’s easy for us all to get stuck in our routines but we always have the fullest laughs and create great stories when we’re together.

5. What’s on your lifetime wishlist?

What are the things you’ve always wanted to buy or experience? Don’t let inhibitions hold you back. List as many material and non-material things as you can think of.

How much would those items cost?

No need to justify these items with a “Why”.

This is a fun exercise to understand what you may want to invest in the future.

My Response

• Material

  • Ocean view from our house or condo

  • My wife would like 1 acre of land

  • ✅ Buy a van and surf up and down the coast

• Non-material

  • See big wave surfing in Nazare

  • Visit Thailand

  • Visit Japan

  • Visit Chile

  • Surf in Indonesia

  • ✅ Get PADI certified

  • Get sailing certified

  • Try mountain biking

Keep your responses saved somewhere so you can look at them again in the future. It’s exciting to start having a guidebook of where to and not to spend your time.

Thank you to Michael Richman for helping craft this exercise.

Last year I spent a lot. ~$600k when my estimate was $400k.

For context, our family unit is my wife, me, and two dogs—a home in California and a condo in Illinois.

I try not to actively hold back spending and enjoy buying things that bring us joy. Trips, dinners, clothing, whatever it may be. I’m not buying watches every month, flying first class much or designer clothing, but it all adds up.

We won’t have to work again from an annual spend like this, but it still is surprising/shocking. At the end of the year, I look at the total spend and realized it’s not the regular monthly spend that throws my “budget” off, but one-off, large expenses.

Historically, I always looked at monthly expenses, and when a large one-off item came through, I said to myself, “Well, that’s just this month”. Maybe you’re like me and find yourself saying that a fair amount throughout the year.

So this year, I’m trying something new to better understand what we might spend.

First, I’ll be looking at spend annually, instead of monthly, to help smooth out the large lumps. I gauge portfolio preference annually, so I should look at spending that way, too.

Lastly, I spent 20 minutes with my wife to write down as much as many one-off things we wanted to do this year as possible. Items like a trip to Europe, Tahiti, Costa Rica, a small home renovation, and visiting a tennis tournament made the list. Anything that may be greater than $2k in spend. I also added a $20k slush fund for things that may arise we want to experience or do.

I then added that list to my average monthly expenses to get a sense of my overall spending for this year.

Hopefully, there are no year-end surprises now.

Keep you posted if it works!

Overall Rating 7 / 10

Summary: This year was incredible, with a heavy emphasis on hobbies, adventures, and better health-based routines. Since we live in different states from our family, we spent 67 days visiting them, more than any previous year. Financially, as my portfolio is a simple 70% equities, 30% fixed income, I had a 7% increase in net work after spending. Personally, my marriage needs communication improvement from years of focusing solely on my previous business.

Family (Rating: 6 of 10)

The positives.

I don’t think there’s a year where my wife and I experienced more together than any other year. We flew 95,000 miles across 12 countries, which also included a total of 13 hours of delays (source: Flighty). Yikes!

I usually would be disgusted at the amount of time spent in airports, but the vast majority was non-work related as we explored new places. Some highlight countries were a safari in Kenya, wine tasting in Portugal, the pyramids in Egypt, watching a pro surf competition in El Salvador, surfing in Costa Rica, eating our way through Mexico City, and camping in Death Valley.

We even bought a camper van to visit National Parks, and our first road trip was driving back to our parent’s home state for the holidays. Being in the van and going anywhere and anytime is incredibly freeing.

We spent 67 days back in our parents’ home state, attending birthdays, holidays, taking family to new attractions, and just being together. I’m really happy we took the time to do this and will continue it.

I think one of the best gifts, though, was sending our parents back home to Taiwan. They had an incredible experience and probably wouldn’t have done it otherwise. Our parents seem to always be busy doing something and can get stuck in their routines.

Ok, room for improvement areas. This section is why I rated Family a 6 of 10.

First, I need to get off my phone more.

It’s too easy to open Instagram and Twitter 20x a day, scrolling around looking for dopamine. Two weeks ago, I deleted the apps off my phone, but I can access them from the browser if need be. It seems to have killed the zombie-like checking, scrolling, and reading, as the browser experience is way worse than a native app. I find myself getting up in the morning without checking my phone, feeling calmer with less inciteful content being displayed, and wasting less time in the bathroom scrolling around on the toilet.

Second, another area for improvement is my marriage. I spent 10 years focusing on my business, half of which was when I was single and not with my girlfriend, now wife. We achieved the holy grail of financial independence: no need for a job or meetings and the ability to spend time how we want to spend it. But the cost was the quality of our marriage.

That business was my sole focus and obsession for a long time, which meant I wasn’t as present and dedicated as I could have been. The theme for me in 2025 and beyond is going the extra mile. Schedule things together that I know she’ll like and experience, even if I don’t. Treat our relationship more like I’m courting her versus having been together for 10 years. We’re also going to hire a couples therapist to help improve communication and a stronger marriage.

Lastly, my wife and I still don’t have a clear direction on whether or not to have kids. We wanted to have a direction by now but don’t. Maybe that’s ok.

Personal (Rating: 9 of 10)

I really went deep on hobbies this year. I hired a weekly surf coach to help me improve. We review video tapes, do gym exercises, and have a roadmap for continuing to improve. It’s been fun to spend money on activities we enjoy. For example, if you enjoy tennis, can you hire a trainer, watch a pro tournament, play at the best-maintained clubs, and really dive deep into it?

I’m still lifting heavy weights 3x a week but added 5g/day of creatine to help reduce soreness. It worked surprisingly well. This is in addition to 150g+ of protein and a few other supplements based on my blood test results.

Since I wanted to add more cardio into the mix, I ran 1x a week for 2mi. Not much, but better than nothing at this point.

Through better food consumption, I’m at 17% body fat. Why a 9 out of 10 then? I eat an insane amount of desserts.

Finance (Rating: 9 of 10)

We spent significantly more than anticipated.

It’s always the large one-off items that blow up my spending plans. Not in a bad way, as it’s not out of control (less than 4% of net worth), but I’m surprised by how much lifestyle creep we’ve had over the past 3yrs.

In 2024, our income was my W-2 income from the acquirer, my wife’s W-2 income, and distributions from fixed-income investments. At some point, we should spend down the principal so as not to let our net worth get out of control, but since we’re in our mid-30s, I’d like to be more conservative.

Home improvements, a sprinter van, and trips dominated spending this year. Some of those are materialistic, and others are experience-driven. I’ve already started creating a rough budget for 2025 with my wife in an attempt to plan for larger-spend items we want to experience or buy. I’m also going to look at spend annually instead of monthly, which gets skewed too often.

Although I track spend using RocketMoney, I’d prefer not to be surprised by larger expenditures. I’ve noticed that I feel “richest” when our spending is below the budget, which may just be a psychological game at this point.

I’ve also never worked on a spending plan together with my wife, as I just create it and give her a heads-up. Not because I’m a budget dictator, she’s just not interested in it. She thinks I worry about money too much, but she has acknowledged that I have improved over the past 3 years since I sold the business. I personally think that once my financial advisor shared a Monte Carlo simulation of our net worth, it made me want to change my spending habits. Visually seeing our net worth balloon to an unimaginable number when we die (I estimated at age 95) means we didn’t take full advantage of the assets.

My goal was to keep spending under $400k. Some of the larger expenditures were ~$20k in home renovations, a $25k trip to the Masai Mara in Kenya this year, and a $200k sprinter van.

After spending, our net worth was up 7%. I was overly invested in treasuries even as the SP500 rocketed, but I am almost fully dollar coast averaged in a 70% equities/30% fixed income allocation. My financial advisor manages the fixed income side as I found it complicated in a high-tax state to deliver the best post-tax gains.

I exclude taxes from our annual spending total, but here are the annual categories from 2024:

• Taxes, $319,973.00

• RV Van, $218,526.53

• Travel & Vacation, $68,840.70

• Property Tax, $65,308.75

• Home & Garden, $56,160.10

• Dining & Drinks, $41,273.36

• Shopping, $31,816.57

• Bills & Utilities, $22,878.29

• Pets, $19,636.35

• 1st Home Mortgage, $79,999 (This is tax-advantaged using a Tax Award Mortgage)

• 2nd Home Mortgage, $18,396.36

• Business Related Expenses, $12,217.59

• Auto & Transport, $11,734.54

• Entertainment & Rec., $10,875.02

• Gifts, 1% of spend, $10,625.59

• Groceries, $9,956.44

• Health & Wellness, $7,276.31

• Cash & Checks, $5,213.88

• Personal Care, $4,214.21

• Legal/Accounting, $2,680.00

• Medical, $2,376.90

• Uncategorized, $2,061.80 (I got lazy on categorizing mostly Venmo’s)

Career (Rating: 8 of 10)

I gave advising for a family office this year a try and quit after 3 weeks. They were a great team, really smart, and had a lot of opportunities to learn about investing. But in the end, it was a drag to join regular meetings again, plus I found it tough to work for someone. I’m happy I was self-reflective about my time and pivoted quickly.

It's safe to say I haven’t figured out my new North Star yet, but maybe that’s okay. We’re wired to work a job to earn income and use that to live daily. If you don’t need income, the equation is broken, and another is needed.

What’s working for now is focusing on spending time where I get positive energy and excitement. If I leave a camping trip, surf excursion, or dinner with friends and feel great afterward, I want to chase more of that.

Do I still get the urge to build a company again? Yes, every few days, in fact. But if that opportunity arises, I’d like to be deliberate about it. It would need to energize me but not drag me into long hours and mentally distance me from family again.

—

I hope you enjoyed my rambling on about 2024. Cheers to 2025!

“Money doesn’t buy happiness” is the old saying.

That’s a damn lie.

Money buys freedom from doing the things you don’t want to. It buys you an ego boost if you crave it. It allows you to be as bored or overbooked as you’d like.

Six months after selling my business, I wasn’t sure how to spend my time. Should I have sold the company? Do I need to rebuild something? Should I become an investor? How about getting into real estate? Maybe I was just lost.

It is oddly easy to get stuck in a doom loop, and lose sight of the incredible life-changing gift we’ve received.

If you’re feeling down or unfulfilled or wish you could go back to running your company, I challenge you to shift your perspective. Every situation we experience has at least two perspectives.

Perspective shifting is one of the most powerful things I found for navigating a post-exit life. We are some of the luckiest people in the world to be able to experience this, a position that anyone would trade you for at any time.

If you perspective shift, you can navigate your days to being present, filled with pure enjoyment, and only doing things that give you positive energy.

I realize now that the faster you’re able to perspective shift, the happier you become.

Tim Ferris wrote it best:

It's frighteningly easy to develop pessimistic blinders and lose sight of the incredible blessings and achievements in our lives. This is common when a single identity-for example, job title and function-leads you to measure self-worth using one or two metrics (like income or promotions, usually in comparison to others) dependent on some variables outside of your control.

Recalibrate your perspective, and prevent over-investment of ego in one area of life, with scheduled gratitude exercises that take a holistic inventory of the positive people and achievements in your life.

New life KPI: Speed to Perspective Shift!

Every piece of clothing I wore had my company name on it. I thought about it first thing in the morning, all day, and every weekend. My company was the first thing they asked about when seeing family or friends. I thought it was who I was and my life purpose. After all, I was on a 10-year mission before selling it.

My ego was intertwined with being a “Founder.”

It was all-consuming, until it wasn’t.

After exiting the business, I thought I needed to do something. “My identity is in building; I need to build.”

Although this “building” urge still pokes its head every few days, even after 3yrs from selling, what changed is realizing my identity wasn’t actually the company. It was overworking.

I defined myself based on how hard I worked. How many hours I put in. Could I be the first one in the office and the last one sending Slacks at night? Could I fix the customer issues, code a feature, do a sales call, and sacrifice as much time as possible for the business?

Thinking back to that time makes me cringe. That lifestyle sucks, and I think we envy it too much. Was it really that great? Key employees quitting, revenue churn, integrations breaking, new hires, scaling problems, the list goes on.

Identifying myself as the hardest worker in the room isn’t for me anymore.

Maybe it had a time and a place to get financial freedom. But letting my ego drive decisions let me to burnout.

I want to allow myself to be highly passionate about projects, but sacrificing all life balance isn’t the solve anymore.

We don’t have to be in charge, make all the decisions, and always be busy anymore. It’s okay to unwind it all. This is a reminder not to let momentum and ego make our future decisions.

Life after selling your business can be a confusing process.

Some jump right back into running another business. Others don’t know what to focus on. Along with communities, I have found this ongoing list of reading materials to help transition over the past 3yrs.

If you’ve got resources you’ve enjoyed, share them in the comments!

A Dozen Questions to Consider After Selling Your Business

“We encourage post-exit entrepreneurs to pause and do nothing for at least six to twelve months. Just to decompress and let go of the beloved company. This can feel like a mourning process…”

Link

A Dozen Questions To Consider After Selling Your Business

691KB ∙ PDF file

Download

Download

The Entrepreneur’s Epilogue and the Paradox of Success

“A four-phase framework to help entrepreneurs process their epilogue and emerge in a new, vibrant chapter: Pause, Reflect, Operationalize, Think.”

Link

What’s next the entrepreneur’s epilogue and the paradox of success

2.29MB ∙ PDF file

Download

Download

Tony Hsieh, Purpose, and The Dark Side of Selling Your Company

“The other thing that helped me was to allow myself to be comfortable with uncertainty. At some point in the future – maybe measured in years or maybe measured in decades – I’ll leave the company I founded. I don’t yet know what I’ll do next. I’ve realized, however, that I gain no psychic benefit by beating myself up over a lack of a plan.”

Link

Tony Hsieh, Purpose, And The Dark Side Of Selling Your Company Linkedin

4.31MB ∙ PDF file

Download

Download

Who shows us how to live — Federer or Ronaldinho?

“It is a skill not to move the goalposts as success pours in, to avoid invidious comparisons with what other people have or do. It is a skill to ‘not worry about the possibility that there might be something better’, as Schwartz puts it.”

Link (Paywall link)

It is a skill not to move the goalposts as success pours in, to avoid invidious comparisons with what other people have or do. It is a skill to “not worry about the possibility that there might be something better”, as Schwartz puts it. What disappointed fans see in Ronaldinho as waste or indulgence is itself a kind of mental discipline — perhaps the highest kind.

Who shows us how to live — Federer or Ronaldinho?

6.79MB ∙ PDF file

Download

Download

Naval’s Most Important Things in Life

“A fit body, calm mind, and house full of love are things that can not be bought.”

Link

The 3-Step Plan to Figuring Out What You Want

“High achievers get really anxious when they don't have an “answer” for what they’re going to do with their life. This causes them to prematurely commit to something - anything.”

Link

The 3 Step Plan To Figuring Out What You Want To Do In Life

5.09MB ∙ PDF file

Download

Download

The Days Are Long but the Decades Are Short

“Making money is often more fun than spending it, though I personally have never regretted money I’ve spent on friends, new experiences, saving time, travel, and causes I believe in.”

Link

The Days Are Long But The Decades Are Short

3.14MB ∙ PDF file

Download

Download

MoneyWise Podcast

Great podcast series with post-exit founders. One of my favorites is a guest, Jeff, who has dedicated his new life to maximizing experiences and zero work.

Link

Die With Zero: Getting All You Can from Your Money and Your Life

“We all have at least the potential to make more money in the future, we can never go back and recapture time that is now gone. So it makes no sense to let opportunities pass us by for fear of squandering our money. Squandering our lives should be a much greater worry.”

Link

The Psychology of Money: Timeless lessons on wealth, greed, and happiness

“Use money to gain control over your time, because not having control of your time is such a powerful and universal drag on happiness. The ability to do what you want, when you want, with who you want, for as long as you want to, pays the highest dividend that exists in finance.”

Link

Life After an Exit: How Entrepreneurs Transition to the Next Stage

“Wealth managers advise that the first and most important questions an entrepreneur should ask after a wealth creation event are: What do I want as my future and my purpose, and how can this money help me achieve my goals?”

Link

Life After An Exit

461KB ∙ PDF file

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Life After Selling a Business

“Will your post-sale lifestyle represent a mini-transition that allows you to largely continue your pre-sale life, with a few key modifications? Or will you embrace a complete reinvention?”

Link

Life After Selling A Business Report

4.2MB ∙ PDF file

Download

Download

Dealing with the Emotional Fallout of Selling Your Business

“Make sure you consciously accept that this will be a process of transition and reinvention, and that it won’t always be peachy. Mourning and drift may be part of the journey, and getting back to “flow” may take longer than expected.”

Link

Dealing With The Emotional Fallout Of Selling Your Business

5.15MB ∙ PDF file

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I really enjoy meeting new people.

If I’m surfing and chatting with regulars, attending social groups, or going to Long Angle happy hours, it’s fun to learn what people are up to. Whether it’s politics, business shares, or just shooting the shit, I feel it’s one of the methods I use to stay sharp.

When these conversations with newer friends go a bit deeper than surface level, the question “So what do you do?” always comes up.

I try to avoid work-related questions as long as possible so we don’t get to that question.

My response tends to be tailored to the conversation. As in, if they’ve sold a business too or are in private equity, I can be transparent right away. Love it! But usually, that’s not the case, and I’m cagey.

Not that “What do you do?” is a crazy question. It’s just that responding with the truth of, “retired” or “sorta work for a PE firm who bought us” sounds ridiculous for someone in their 30s. It also creates more questions I don’t want to get into regarding the exit and such.

I’m trying different responses, though:

• “I’m in tech” - Works well but can create more questions around what company, etc

• “Work at a software company” - Not bad, but similar result as “I’m in tech”

• “I run a small software company” - Seems to work well. No further questions generally, maybe it’s the word “small” turns people off.

The problem is if someone starts to curiously ask further questions, “Oh really, how many people work there? What’s your role? How’s the business?”, my responses tend to go down a sorta truth/lie after sorta truth/lie rabbit hole.

If a friendship starts to form, though, I’ll share a bit more, saying, “Well, I had a company, but it was bought. It was a small thing, though. I’m looking at new ideas.”

Sorta truth/lie, sorta truth/lie still, but that feels a bit better.

I’m curious, what do you say? Respond in a comment below!

Leave a comment

I’m stuck in Nairobi Airport right now.

Our flight had a short layover with an end destination in Cairo, Egypt, but it just got canceled. The connection to Cairo is unknown. Worst yet, the airline won’t release our checked luggage. This throws a big wrench in our plans as we have a tight schedule for tours, restaurants, and other flights.

People are PISSED. Rightfully so, as the airline hasn’t given any information for hours and has been unhelpful in rebooking connecting flights. I understand their perspective.

We have to get out of here, though. It’s a complete mess and frustrating, with little to no customer service.

My wife and I quickly glanced at Google Flights for another airline to take in the morning. The only two seats available are in business class on a direct 5-hour flight out. It’s  $4,098.38 and departs at 6 a.m.

Oof.

That’s really expensive for a fairly short on-way. Is it really worth it? Could we meander around and hope the original airlines fixes everything?

I don’t usually buy business-class tickets, so this feels crazy. After a few minutes, we booked the flight and a hotel to sleep in for the next 4 hours.

While we were walking to the airport hotel, I texted a friend back home about what happened. Towards the end of the conversation, I asked how his kids were doing, as the second was just born. They live in Chicago, in a two-bedroom apartment, which works well with two kids under two. He said, “We don’t sleep much, but we’re so grateful they’re healthy, and we can all live in the city.”

That made me think. Every situation has two perspectives. You can be frustrated, want to vent and be pissed off. Or, you can be grateful for the situation you’re in. Being financially independent amplifies the ability to be envious or grateful, and we can choose.

Frustration is always the easier out. It’s harder to twist a situation into a positive and roll with the next steps.

I feel my expectations have grown since my exit a few years ago. It’s easy to want more and expect it sooner. And with that, brings less time to step back and just be grateful.

We literally had the ability to buy our way out of this crappy flight situation in Nairobi while others have to sit and wait possibly days more to get moving. That’s unbelievable!

Fuck being pessimistic, frustrated or envious, We have the greatest life ever and I’m so thankful for it. This is a reminder to me to take a second and be grateful in life.

I’m just about to start a trip to Africa with my wife. We wanted to stop over in Jordan to sightsee the country and, of course, visit Petra. Because of conflicts in the area and airlines not flying to Amman, we decided to change course at the last minute. 

We booked a flight to Lisbon, Portugal and figured why not stay longer than originally planned. 

I realized that this ultimate time flexibility is Peak Top. 

I went to a Hampton talk with Sam Parr and Rob Dyrdek in Los Angeles a few months ago. Rob is an animal of sorts. Super energetic, financially successful, and fanatic about how he spends his time. 

The one thing that stuck with me after leaving with his passion for Peak Top. 

Rock Bottom is defined as “the lowest possible level; the most unhappy that someone has ever been in their life.” 

Peak Top is the exact opposite. It’s complete time flexibility, financial freedom, and life optimization. It’s spending the majority of your time doing things that excite you with the people you want.

If you are lucky enough to have your health and be financially free of working again, you should strive for Peak Top. 

See you there!

I’m one of the luckiest people in the world, but I can’t help but crave more.

I remember watching an HGTV episode in my early 20s about a couple building their dream home in California. It was an indoor-outdoor home with floor-to-ceiling glass panels that let in an extraordinary amount of natural light.

I thought to myself, wow, that would be amazing to live in one day.

Fast-forward ~15 years. I live in a home like that in California, with big glass windows, indoor-outdoor living, and lots of natural light. Sure I worked hard, but my wife and I are unbelievably lucky and fortunate.

Do you know what would be nice, though?

An ocean view would be cool. Oh, and what if we lived in an area walkable to a surf break? How about a second home in the country? Lots of land sounds nice. Maybe a rooftop? I see those G-Wagons driving around a lot, that would be fun to drive.

How fucked up is that mindset?

In my 20s, I couldn’t have imagined the life we live now.

I have all the financial security I could ask for, a beautiful home, the ability to control my time, who I spend it with, and I still want more. Much more.

Maybe it’s because I’m exposed to things I haven’t seen before. Exotic vacation locations I couldn’t fathom flying to. Places to live that were out of reach. Or maybe it’s living in an area surrounded by HNW individuals.

It seems my standards continue to grow. Maybe it’s just human nature or just being in your 30s? Hard to know.

Do you feel the same way? Or are you completely satisfied?

Either way, thanks for listening to my random thoughts.

Most post-exit folks I’ve met are bad spenders, including me. 

No, they’re not spending on the wrong things. They’re just not spending enough. 

We’re some of the luckiest people in the world. And if you’re not increasing your spending, you’re not taking advantage of this unique position. 

But it takes time to build this skill.

It could even take years to feel comfortable increasing your annual spending. While being financially responsible, try pushing it to the limit.

Look. If you’re lucky enough to be in a position not to need to work again but are hoarding capital like it’s your last dollar? Time to consider a change. I still love saving $1 at CVS or selling things on Facebook Marketplace, but I’m also building my spending skillset. 

Maybe it’s momentum from being frugal growing up or how our parents raised us to save as much as possible.

Wouldn’t it be a shame if you didn’t have ultimate life fulfillment post-windfall? The ability to create life experiences most can only dream of—the flexibility to take complete control over how you want to spend your time.

We have to take full advantage of this. 

Don’t know what to spend on? Try some of these:

• Send your parents on a trip. It doesn’t have to be to Japan; it could be to San Diego or locally for a staycation. 

• Get your family member’s dirty car a detailed cleaning. 

• Buy your partner that jewelry they’ve talked about. 

• Upgrade your seats on the next flight. 

• Take a helicopter tour of your city. 

• Enjoy working out or just started? Upgrade all your gym clothes with Lululemon or Vuori.

I’m saying “yes” a lot more.

I probably overbooked myself with trips, adventures, friend excursions, and everything in between for 2024. But this year, I wanted to max out fulfillment. 

Give it a try!

How about what they spend and why?

Tad Fallows is Co-Founder of Long Angle, a community for high net worth individuals to ask questions and learn from each other.

In this episode we dive into:

• How Tad came into wealth

• Moving from Californiato Texas and if he’d recommend it or not

• Vacation homes and increasing lifestyle spend

• Defining Tad’s Rich Life

• Journey of starting Long Angle

We have different seasons in our lives.

There’s a college season. Filled with homework, parties, tests, and sports.

There’s a new college grad season. Having an ego, wanting to move up quickly in the workforce.

An entrepreneurship season. The grind, working as long as your eyes will stay open. Pushing through someone quitting, rehiring, closing sales, and making product decisions.

Other times, it’s a family season. A family member may be sick or just spending quality time together over the holidays.

And if you exited your business, life takes a turn into a new season too. Things get very different. Although you may be financially secure, the craving for action and what’s next creates anxiety.

I’m not convinced we really want action though. That’s just inertia speaking. It’s the years of toiling away at problem after problem. To take it a step further, I think it takes a few years of decompressing to understand what we really out of everyday.

My first year after selling, I wanted do something immediately.

Time to build! Or wait, should I be an investor?

Let’s start a new app, I’ll crack open my Ideas doc. Should I buy an app? Everyone’s talking about acquiring micro-SaaS companies.

I ended up taking the first two years slowly. And not doing much of anything. I’ve enjoyed being by the ocean, surfing, saying yes more often to get-togethers, seeing family, being more present, helping my wife in her career, taking photos, and just being bored.

I’m glad I didn’t commit to anything career-wise though.

I still get the itch. The craving to grow a business and create real value for customers and investors. Why not dive back in? But that’s inertia speaking!

I’ve been writing down the things that give me joy during a week. So far I have:

• Morning surf

• Gym / strength training

• Being available when my wife comes home

• Having time flexibility to take last minute trips

• Saying “yes” to experiences more, even as small as lunch with friends

• Ability to be home with family longer without distraction

• Thinking through business problems fellow entrepreneurs have

• Writing on this blog

I wrote them down because it’s easy to let inertia take ahold and jump back into a business.

What I’m realizing is, It’s okay to be bored.

It won’t last forever. Nothing generally does, it changes in seasons.

In fact, this season may never happen again. My wife and I might have kids, she could get busy with her business, my parents’ health may decline and need more help. Who knows!

But for now, I’m accepting that it’s okay to be bored.

Executive Health Results

Longevity is the talk of the town. From Peter Attia, to Huberman, and Bryan Johnson, it seems everyone (at least in the tech world) wants to optimize their health.

Ryan recently signed up for a concierge doctor. We’ll dive into how much it costs, the process, and his results.

Goal Setting

I used Jesse Itzler’s Big A## Calendar for goal setting this year.

It was the first year I’ve set goals. Taking after Jason Fried’s thought process when I ran my business, I felt goals added unnecessary stress and missed short-term opportunities.

But this year, I felt different. I wanted more structure in my personal life and a plan for 2024.

Ryan went about this year’s planning in a unique way too. He did a deep dive with his wife into what they wanted together using Justin Donald’s Marriage and Family Planning Workbook.

2yrs Post Exit Lessons

I wrote a longer list of what I’ve learned in the past 2yrs after selling my business.

If you start another business, does it have to go bigger? Or is that a trap? Ryan and I chat about this along with our biggest learnings.

Hope you enjoy the episode!

Tony Hsieh sold Zappos to Amazon for $1.2b.

An incredible amount of money, community praise for his work on creating a customer-focused company, and unlimited opportunities to figure out what’s next. All sounds incredible from the outside.

Turns out, Tony was working through mental health issues and loneliness.

Everyone deals with post-exit life differently. It’s a big shift, and something you can’t openly “complain” about. You’re going to tell your best friends you’re depressed after making many lifetimes of money? C’mon.

Fortunately, there are communities you can tap to help. I highly recommend joining if you haven’t already.

I came across this David Rodnitzky article who broke down post-exit angst into 4 pieces. It’s great to lay out on paper to attack head on. Let me know what you think!

Take a read here or download the PDF below.

Tony Hsieh, Purpose, And The Dark Side Of Selling Your Company Linkedin

4.31MB ∙ PDF file

Download

Download

Stolen credit card numbers, your home address online, SSN exposed.

These are things we don’t think about until something bad happens. Cybersecurity Ventures expects global cybercrime costs to grow by 15 percent per year. Warren Buffet calls cybercrime the “number one problem with mankind.”

The unfortunate part is that this trend is only going to increase with AI and more advanced threats.

You have more to lose than the average Joe, so how do you protect yourself?

I recently listened to fellow Long Angle member Jared Ablon give a talk about improving your cybersecurity. He shared the practical steps to reduce the risk of stolen information.

In 2hrs, I executed everything he said to put myself in a better position security-wise. Some of this can seem daunting but makes it harder for a hacker to penetrate, thus encouraging them to move elsewhere.

Jared graciously offered his email, jaredablon@gmail.com for more information or for trusted security professionals to help you accomplish everything.

Here’s what I learned:

Mitigate Social Engineering Attacks

• Minimize your data footprint online and off

  • Be paranoid: Zero trust by default.

  • Go through your Google Drive/Dropbox/Box account, delete old documents with PII (personally identifiable information).

  • Do not trust emails/attachments you receive; call the sender if you have a bad gut feeling.

• Before sending wires, call the sender to verify information.

• Do not click on unknown links; inform everyone in your household to do the same.

• Use common sense (e.g., do not send Bitcoin to Joe Biden).

• Be careful with what you post (e.g., don’t post your CDC vax card with your DoB)

• Always hit the SPAM button for unsolicited emails

  • Do not “unsubscribe” because that validates that you have a valid email address

• Never email anything you want confidential - “Email is like a postcard.”

• Avoid using debit cards/bank information online in written form.

• Delete old accounts you do not use – social, email, etc.

• Have a trusted passphrase among family/friends to mitigate AI tools spoofing voices. (This is scary).

Mitigate Phishing and Ensure Privacy

• Sign up for DeleteMe to remove content from the web and data brokers (Kanary and OneRep are other providers)

  • White Pages, Mylife, Spokeo, etc. are providers that buy and sell your data.

• Ask the Wayback Machine to delete archived content.

• Ask Google to remove PII.

Tip: If you’re in California, California’s Consumer Privacy Act (CCPA) allows the state’s residents to obtain copies of the information data brokers have collected on them. This act also permits California consumers to request the erasure of their information and opt out of having their data sold.

Mitigate Compromised Credentials

• Use a password manager. I prefer 1password (others are Lastpass and Dashlane).

  • Each website you create an account or login, can now have a unique password that is stored in 1password.

  • This also allows for sharing passwords without divulging the actual password.

• Enable 2-factor authentication on everything.

  • Preferably non-SMS-based 2-factor authentication, as SIM hacking can happen to your cell phone.

• If you store information on a Dropbox-like service, go through 3rd party access. You’ll be surprised what still has access to your account.

Reduce Risk of Exploits

• Only download apps from trusted sources (e.g. Google Play™ or the App Store®).

• Do not use removable media (CDs, USBs, etc.) unless from a trusted source.

• Avoid using airport USB charging ports.

• Keep software up-to-date. Even better, enable auto update of apps and OS where applicable.

• Run anti-virus software on Windows.

• Avoid public wi-fi if possible.

  • If you must, use a VPN. I use NordVPN.

• Never buy used computer equipment.

• Change your home internet’s router default password.

• Never ignore your browser warnings or go to non HTTPS websites.

• Go through your computer/phone and remove applications you do not use.

• When installing new software, only give applications the permissions they really need.

Lost and Stolen Asset Protection

• ​​Turn on Full Disk Encryption (Mac / Windows) on all devices.

• Turn off laptops when traveling.

• Turn on a password-protected lock screen for computers and mobile devices.

• Have the lock screen auto-turn on after 3 minutes of inactivity.

• Do not sell old computer equipment on marketplaces.

  • Securely dispose of computer equipment (phones, laptops).

• Use pins when possible; TouchID/FaceID is not the most secure.

• ​​Turn off Bluetooth on all devices when not needed.

• Share location services sparingly.

  • You can be tracked, and people can know when you are at home, work, etc.

  • Only share location services on certain apps and turn them off when not needed.

• Use offsite secure backups. Backblaze has been a popular option.

Beyond the Fundamentals

• Freeze credit with Equifax, Experian, and TransUnion.

• Create a home guest wi-fi network.

• Create an account for all online transactions (ACH, Wires, etc). Only keep the cash necessary for these transactions. Keep the bulk of your cash elsewhere.

• Advanced

  • Have a banking-only laptop/computer. JPM has an option to only allow login to certain IP addresses.

  • Have an air-gapped laptop/computer that does not have internet access. This would be to store secure, PII-filed files.

  • Use hardware tokens to login to brokerages, etc.

  • Put a firewall in your home (with VPN capabilities).

You’ve done the hard work to sell your business. Something only a few experience with potentially a life-changing amount of money now your bank account.

The endless due diligence meetings, emotional roller coaster, calls with attorneys, team announcements, and everything in between are now over.

Now what?

Prepare for a wide range of emotions.

• What should I invest in?

• Everyone has real estate, should I?

• What should I buy?

• What does the money mean for me?

• Do I get my parents a car?

• Should I be an investor now?

• Who should I tell?

• How will people view me?

Guess what? The beautiful thing here is you don’t have to do anything.

That’s right, you don’t have to change your life, house, friends, or investments. You don’t need to tell anyone.

New wealth takes time psychologically to adjust to. Here’s an example. Dollar cost averaging a percentage of your salary each month and investing into makes sense. You do it each month, are accustomed to it, and may not think much about it.

You received a windfall; percentage swings in physiologically are harder to stomach now. Dollar-cost averaging isn’t as easy, and you sit on the sidelines.

I’m 2yrs in and still have a lot to work through. But, my point is. Understanding your new life, investments, and goals takes time, and that’s okay. Take time to reflect and think about what really makes you happy. What are your priorities now? What do you care about, and what gives you joy? This may have all shifted.

It may take a year; it may take two. It may take many more. Give yourself the time and eliminate the expectations.

1. Financial advisors are like real estate agents; most are bad. But the few that are helpful can be a value-add.

2. Psychology affects market returns. Dollar-cost averaging a portion of your salary differs from allocating $50m. Theoretically, you may know what to do, but it’s difficult to pull the trigger in reality.

3. Switching from living on w2 income to a portion of your portfolio is a difficult mind shift.

4. Whoever you tell about your exit will tell others.

5. Prepare to be lost, identity-wise, for a few years. It’s okay and normal. More on this.

6. I’m more risk-averse than I used to be. In a sense, I won the lottery. Why risk it?

7. Taxes are a significant expense I don’t spend enough time on. I’m working on this. Consider tax loss harvesting, a strategic CPA, municipal bonds, your primary state, etc.

8. I did the hard work, but timing is everything. I was lucky to exit in a hot year that drove massive returns.

9. It took me 1 year and an Antarctica cruise with terrible cell service to physically separate myself from the business. I had to be forced to unplug.

10. I’m more present than ever in enjoying every day. This feels like personal growth.

11. People who say “money isn’t everything” are liars. Managed well, it gives ultimate life flexibility.

12. I should have considered what I wanted to spend my time on before exiting. I had to spend time on that afterward instead.

13. Everyone invests differently. You won’t get one size fits all. Whatever lets you sleep at night while giving you financial freedom = win.

14. Psychology of Money was a game-changer book for me to understand what “wealth” is. Here’s my summary.

15. Your real friends/family don’t care about your wealth.

16. I recognize things I don’t own, but want because they’re flashy, is because of “envy”. Realizing that helps not buy it and move on.

17. Regaining motivation for work is difficult.

18. Spending well is a skill. Not over-spending, but utilizing your wealth to make your life awesome.

19. Legacy is overrated. You won’t be remembered by more than your close family in 50yrs.

20. Want to eat healthy? Keep the house clean? Maintain the yard? Wrap presents? Hire someone. Allow yourself to be happy for more hours of the day.

21. It’s great watching the new CEO execute. I realized was way too ingrained in my business. I should have delegated a lot better.

22. People that know about your sale think it’s amazing and envy you. Be careful of that ego boost.

23. Do you want to buy a house but don’t understand how much you can afford? Use the monthly payment + tax + maintenance as a guide. What’s a comfortable all-in monthly payment is how much house is doable.

24. Privacy is important. Use a service like DeleteMe to wipe your phone number and address off the web.

25. Join a HNW community to learn, complain, ask questions, and thrive from others.

26. Money means nothing if you’re not healthy, overspend there.