Are You Over-Optimizing Your Finances? Chris Hutchins from All the Hacks on the 80/20 Rule

Written By Ryan Morrison

Listen to This Episode On

 
 

Introduction

When you're building wealth, there's a natural tension between maximizing every opportunity and protecting your most valuable asset: time. Chris Hutchins has spent nearly five years exploring this balance on his podcast, All the Hacks, which has grown to over one million listeners. A serial entrepreneur who sold companies to both Google and Wealthfront before becoming a content creator, Hutchins has accumulated millions of credit card points and interviewed hundreds of experts on personal finance, travel, and health optimization.

In this episode of Navigating Wealth, Hutchins shares his framework for knowing when optimization is worth the effort and when you should take the simpler path. From the optimal number of credit cards to carry to how he talks about money with his young daughters, the conversation offers practical insights for anyone trying to make smart financial decisions without turning it into a second job.

 

Guest Snapshot

Guest Name: Chris Hutchins

Titles: Host of All the Hacks Podcast, Former Partner at Google Ventures

Credentials: Serial entrepreneur (co-founded Milk, acquired by Google; co-founded Grove, acquired by Wealthfront), made 40+ seed and early-stage investments at GV, accumulated millions of credit card points

Current focus: Creating actionable content on financial optimization, travel rewards, and life hacking through his weekly podcast and newsletter

Additional areas of expertise: Health optimization, parenting, entrepreneurship, venture capital investing, and building sustainable content businesses

 

The Evolution from Extreme Optimizer to Strategic Simplifier

Early in your career, every dollar matters. You're willing to spend hours researching the best credit card signup bonus or finding ways to manufacture spending for miles. But as wealth and income grow, the calculation changes completely.

Hutchins described his own journey: "When you're earlier in your career, when you're earlier in your wealth journey, it's like every dollar counts. And then you get to a point where you're like, well, actually every dollar doesn't count and I'm optimizing for time. I'm not optimizing for money as much."

He used streaming subscriptions as an example. You could get a credit card that earns 5X points on streaming services instead of 2X or 3X. But if you only spend $500 annually on streaming, those extra points translate to minimal value—maybe $10 to $20 depending on how you redeem them. The mental energy and account management overhead simply isn't worth it.

This philosophy extends across his entire approach to optimization:

  • The 80/20 rule applies everywhere, and you get to choose which areas of life deserve the extra 20% of effort

  • Fun matters—if you genuinely enjoy optimizing something, the time investment feels different

  • Complexity has a cost that compounds over time through account management, remembering passwords, and tracking various systems

The key insight: optimization isn't about perfection. It's about intentionally choosing where to apply your energy based on both potential return and personal interest.

 

Credit Cards: The Two-Card Strategy for Busy Professionals

After building what Hutchins called "a model that was way more complicated than anyone listening needs to play with," he arrived at a surprisingly simple conclusion: two credit cards is the optimal number for most people who want strong rewards without constant management.

The logic is straightforward. Most credit cards fall into two categories: cards that reward all spending at a decent rate (2-3%) or cards that reward specific categories at higher rates (3-5X on dining, travel, groceries, etc.). Very few cards do both well.

For the Cash Back Simplifier

If you prefer cash back and can put $100,000 into a Bank of America brokerage account (which can be an IRA or just sit in Treasury bills), the Bank of America Premium Rewards Elite card becomes hard to beat:

  • 2.625% cash back on everything

  • 3.5% on travel and dining

  • No need to think about categories or transfer partners

That $100,000 threshold might sound high, but for someone with substantial assets, it's a reasonable amount to park in treasuries or a diversified portfolio. You're not locking it away—it's still invested and liquid.

For the Points Maximizer

Hutchins mentioned that the newly launched Built Palladium card offers even higher returns for those willing to manage a bit more complexity:

  • Effectively 4% back on all spending (in the form of transferable points)

  • The catch: rewards are capped based on your monthly housing payment

  • You need to change how you pay your mortgage or rent

  • Tax payments don't earn points

If your housing costs are $10,000 monthly, you can earn these elevated rewards on up to $120,000 in annual spending. The key limitation is that you can't just pay estimated taxes and rack up massive points—a strategy that some high earners have used with other cards.

The Real Cost of Too Many Cards

Going beyond two cards means:

  • Tracking multiple billing cycles and payment dates

  • Managing various category bonuses that change quarterly

  • Remembering which card to use in each situation

  • Dealing with more accounts when reviewing statements for fraud

For someone spending a few hundred thousand annually on cards, the difference between a perfectly optimized wallet and a two-card strategy might be $500 to $1,500 in additional value. That's not nothing, but it's also not life-changing money for most high-net-worth individuals.

 

Using AI to Cut Through Financial Noise

Five years ago, if you wanted to optimize an area of your life, you had two options: spend hours researching or find someone you trusted who had already done the work. Today, Hutchins has a different answer: use AI to cut through the noise.

"I can't tell you the number of people who have found me through LLM," he explained. "If you want my opinion, chances are it's getting indexed by an LLM and you could just go ask an LLM that knows more about you and gets a tailored answer."

Practical Applications

Hutchins shared several specific ways he uses AI tools like ChatGPT and Claude:

Blood work analysis: After getting lab results back, he uploads both his previous and current tests and asks questions like "What changed? What matters? What's going on here?" This replaces what would have been hours of manually creating spreadsheets and charting biomarkers.

Personalized software: "You want to build a piece of personalized software? Before you would raise money and hire a team. Now you'd spend 30 minutes in Cursor or Claude Code and just have the tool you want."

Skeptical prompting: Hutchins emphasized the importance of not accepting every AI response at face value. He prompts models to be skeptical: "Don't just be a yes person. There's nothing that makes me more mad than when any AI tool is like, 'that's such a great idea.' I'm like, no, maybe it's not a great idea."

The real power is that the 80/20 rule has shifted. You can now get to 99% of optimal with only 60-40 effort because of these tools. They handle the research, data processing, and even building custom applications that would have required professional developers just a few years ago.

Finding Trusted Sources

Matt Schectman raised an important point: with so much information—and misinformation—available, how do you know what to trust? The problem isn't lack of advice; it's the overwhelming volume of advice, much of it conflicting or self-serving.

Hutchins recommended a two-part approach:

  1. Find people you genuinely trust through track record and consistency

  2. Use AI to synthesize and personalize their insights for your specific situation

The combination lets you benefit from expert knowledge without needing to become an expert yourself in every domain.

 

Travel Rewards: When to Splurge, When to Save

One of the most interesting parts of the conversation centered on travel spending, particularly when traveling with family. The question that comes up for many successful people: should you fly your kids in business or first class, or is that setting them up with unrealistic expectations?

The Framework for Decision-Making

Hutchins shared his approach through a specific example. Recently, his family had a 13-hour daytime flight. They had enough points to book business class for everyone, but he wanted his two daughters—ages three and five—to experience economy.

His reasoning: "I wanted them to see what a 13-hour flight in economy was like. Because I did not want them to think that the way we normally travel is just how everyone travels everywhere."

The kids made it about eight hours before the complaints started. The point wasn't to make them suffer—it was to build appreciation and context for when they do travel in premium cabins.

Rules That Make Sense

When asked if he'd ever make the kids sit in economy while he sat in business, Hutchins said probably not once they're old enough to be on their own. But he did share some practical guidelines:

For short flights (under 4-5 hours): Economy makes sense for the whole family. The comfort difference isn't dramatic enough to justify the cost or points.

For long international flights: If you're using points and have them available, business class for everyone becomes reasonable.

The in-between scenario: If you're paying cash and the business class tickets are $5,000 to $7,000 each for the kids, economy might make sense while parents enjoy a more comfortable experience.

The underlying principle: kids should understand that premium travel is a choice and a privilege, not a default expectation.

Teaching Value Through Experience

Hutchins gave another example that illustrated the challenge: His daughter was at a pool during a staycation Airbnb rental and asked, "Where's pool service?" The assumption that every pool has someone taking food and drink orders showed how quickly kids normalize whatever they experience regularly.

These moments require constant conversation. "Parenting is hard," Hutchins admitted. "You need to hammer on these things all the time." The solution isn't to avoid nice experiences—it's to consistently contextualize them and balance them with more typical experiences.

 

Raising Kids Who Understand How Money Works

The challenge of raising children who understand money and value despite growing up with access and opportunity came up repeatedly in the conversation. It's a concern that many successful entrepreneurs and professionals share.

What Worked for Hutchins Growing Up

Hutchins credited his parents with instilling a good relationship with money and value, even though they exposed him to premium experiences through points and miles. One of his earliest travel memories is sipping apple juice on the Concorde because his father had accumulated points through business travel.

"I grew up also going on these points and miles adventures and getting exposed to it," he recalled. But his parents never just gave him unlimited access to money. At boarding school, while other kids had credit cards from their parents to spend freely, Hutchins took the bus from Alexandria, Virginia into DC instead of taxis with his classmates.

"I felt like I wasn't spoiled and privileged in the moment when in reality, obviously, I grew up in a very fortunate household," he reflected.

The Role of Transparency

What made the difference? His father walked him through exactly how the travel rewards system worked every single time they used points for a trip.

"Here's how we're able to do this. This isn't just that we're fancy and we spend all this money. We almost always just sit in coach. Or if we get upgraded, it's because we earned these points, because I fly for work."

This transparency helped young Chris understand that the premium experiences weren't about unlimited wealth—they were about strategic optimization and work-related benefits.

Current Financial Strategy with His Own Kids

Hutchins now applies a similar philosophy with his own daughters:

Open conversations about money: Rather than treating finances as a taboo topic, he discusses money and travel decisions openly as a family.

Explaining the "how" and "why": When they do travel in business class or stay somewhere nice, he explains that it's through points, or why they're making that choice for this particular trip.

Balancing premium and standard experiences: Intentionally mixing economy flights with business class, standard hotels with luxury properties, so kids see the full spectrum.

Context through peer groups: Who your kids spend time with matters enormously. Even within wealthy communities, different families have different approaches to spending and lifestyle.

The goal isn't to make kids feel guilty about their advantages or to hide the family's financial success. It's to build an understanding that these things are choices, not entitlements, and that many people live differently.

 

Two Quick Hacks Anyone Can Implement Today

As the conversation wrapped up, Hutchins offered two specific tactics that anyone can use immediately, regardless of wealth level or how much time they want to invest in optimization.

1. Check for Unclaimed Money

Every state maintains a database of unclaimed money—forgotten security deposits, uncashed checks, old insurance refunds, closed bank accounts with remaining balances. The amounts vary wildly, but Hutchins consistently hears stories of people finding anywhere from $100 to tens of thousands of dollars they didn't know existed.

"No matter if someone listening to this has $100 million or $100, I promise that no matter what level of wealth you're at, if you find out that someone owes you a thousand dollars and you can get it back, you are going to be stoked."

He noted something interesting about human psychology: people will often spend more time and energy recovering $100 that someone owes them than they would trying to save $100 on a purchase. Once you know money is yours, you want it back.

Action item: Go to your state's unclaimed property website and search your name. It takes just a few minutes, and the upside is entirely one-sided. You'll either find nothing (and lost almost no time) or discover money you didn't know about.

2. Email Hotels Before You Arrive

If you're staying at a hotel—particularly something nicer than a budget chain—book directly with the hotel and then email them before you arrive. Not through the booking platform, but directly to the property.

You can usually find an email on the hotel's website, or call the front desk and ask for a manager or sales contact. The message should be simple: you're excited to stay with them, mention if you're celebrating anything special, and thank them in advance.

Hutchins couldn't quantify the exact success rate, but estimated that one in three times at a reasonably nice hotel, something good happens: room upgrades, birthday surprises for kids, complimentary drinks or parking, or unexpected amenities.

Why it works: Hotels want to create memorable experiences for guests who book directly (not through third parties like Expedia, where the hotel gets lower margins). A simple email gives them the opportunity and context to do something special.

Action item: If you have a hotel stay coming up, send a brief, friendly email to the property 1-2 weeks before arrival. Include your confirmation number and dates. Don't ask for anything specific—just express enthusiasm about your visit.

 

Memorable Quotes

"When you're earlier in your career, when you're earlier in your wealth journey, it's like every dollar counts. And then you get to a point where you're like, well, actually every dollar doesn't count and I'm optimizing for time. I'm not optimizing for money as much."

"The 80-20 rule applies in every aspect of your life, and in some you want to go to the 20 and some you don't. For me, this is fun. I enjoy going down the rabbit hole on travel optimization, credit cards, and points, but in some other areas of my life, I'm just looking for the 80-20, or like the 60-40 even."

"The optimal number of cards to really dial in everything is two. There is one card that is your catch-all and one for specific categories."

"I can't tell you the number of people who have found me through LLM. If you want my opinion, chances are it's getting indexed by an LLM and you could just go ask an LLM that knows more about you and gets a tailored answer."

"The 80-20 is really cool now because you can get to the 99-1 with like 60-40 work because of all the tools we have access to."

"I wanted them to see what a 13-hour flight in economy was like. Because I did not want them to think that the way we normally travel is just how everyone travels everywhere."

"My goal is to just try to be really open as possible about money and travel and everything we're doing and hope that kids pick up on those things as we talk about them as a family."

"No matter what level of wealth you're at, if you find out that someone owes you a thousand dollars and you can get it back, you are going to be stoked."

 
 

Enjoying Navigating Wealth? Subscribe to our weekly newsletter to receive updates when new episodes release and other insights from inside Long Angle's community.

Ryan Morrison
Next

How to Sell Your SaaS Company: Lessons from the Highest Deal Volume Year Ever