We don’t communicate with numbers enough. Numbers are clear, concise, and leave zero room for misunderstanding. Instead, we default to squishy words with ambiguous meanings.

Several years ago, I traveled to Las Vegas for the International Builders’ Show. I attended a dozen classes about finance and homebuilding, but the most impactful presentation focused on team communication.

The speaker asked the room to think about the word “often”. What did the word mean to us? How did we feel about it? After a moment, he continued:

“If I told you that something happens ‘often’, how many times out of 100 do you think it occurs?”

The crowd of 200+ submitted their answers through a website poll. The opinions were quickly tallied and graphed. The results showed a bell curve that ranged from 35 to 80!

“How” the speaker asked, “is it reasonable for us to communicate if one person thinks ‘often’ means 35% of the time and someone else thinks it means 80%?”.

We might both speak English, but if our definitions of a word are that different, then we aren’t speaking the same language.

This chart is a cool visual of the same idea. Look at how wide some of the ranges are! These are words in our everyday vocabulary that have a huge variance in how different people perceive them.

These probabilistic phrases mean different things to different people. There is no shared definition that lets us be certain that we’re on the same page.

I’ve seen this picture floating around online before. It’s a great example of how much stronger our communication is if we avoid subjectivity.

The more objective we can be, the more likely we are to be understood. And the best way to be more objective is to use numbers.

The first example in the image illustrates this perfectly. “Increased significantly” could mean anything depending on the context and on our own perceptions of what ‘significantly’ means.

I’m going to guess that the writer and reader wouldn’t have agreed that “increased significantly” = 40%.

Using the number leaves zero room for error. It doesn’t matter what language you speak or your cultural background. Anywhere around the world, 40% means 40%.

Sure, there’s times when you don’t have exact numbers handy. Even an estimated numerical range is better than nothing.

I’ve been trying to focus on communicating with numbers more. When someone tells me that a project “shouldn’t take that long”, I’ve been pressing for a ballpark. Does that phrase mean 3 days? 8 weeks?

The answer is entirely dependent on context (and opinion). 8 weeks would be record speed to build a house but an eternity to update text on a website.

As much as I can, I’m trying to eliminate the following from my vocabulary:

Sometimes, frequently, occasionally, all the time, often, rarely, regularly, constantly.

Everyone has their own understanding of what those words mean. Instead, I’m trying to replace those types of phrases with numbers. Telling someone that “around 20-40% of users experience this issue” is a hell of a lot better than “some users experience this issue”.

Communication is hard, and subjectivity makes it even harder. We all have the same definition of 50%, 75%, or 95%. Replacing our descriptive words numbers will improve our communication.

Try it out yourself. It should help pretty often.

Not a single hand was raised. An awkward silence washed over the class on day one.

Finally, I raised my hand to answer: “the present value of their discounted future cash flows”.

As the only undergrad in the room, I’d sat at the back of the room on purpose. Now I could feel 75 MBA students turn to look at me, then look back at the professor as he nodded yes and continued the lecture.

I took a deep breath and the imposter syndrome faded away.

As an undergraduate, I had managed to talk my way into an MBA-only class. The average student was 5 years older than me. These were “real adults” with actual work experience!

I thought I’d just be a 21-year-old trying to keep up. What I didn’t realize was that being slightly out of my depth was right where I should be.

I did more than keep up. I thrived in the class and had fun learning how to develop a pitch and demo for a tech startup.

More importantly, I was reminded that growth accelerates when you take on things you’re not quite ready for. It’s not easy. It takes effort. Pushing yourself to take on new challenges can be uncomfortable in the short term but it’s the only real way to develop and grow.

If you stop actively pushing, inertia takes over. Comfort follows and stagnation isn’t far behind.

The first time someone explained this idea succinctly was during a college internship.

Our class of interns regularly had speakers from the executive team come to give their career lessons and advice.

The only one I remember came from an executive who told us that we should only ever be 90% competent at our jobs. Max. He told us we wanted to always be 70-85% competent, and if we ever hit 95%+ then that meant it was time to go look for a new role.

The audience was a group of college students that were constantly freaking out about grades, extra-curricular activities, and how to set up the perfect resume to get a full-time job after graduation. The population was heavily skewed toward Type A.

It was absurd for this group of overachievers to hear from a seasoned professional that they shouldn’t be that good at their jobs? To not be perfect?

His point was that you don’t want your learning curve to get too flat. You want to be in positions where you’re slightly out of your skis to maximize your growth.

In hindsight, the executive was right. The college kids couldn’t quite contextualize the value of not always getting an A. Real growth only happens at the edge of your abilities. Being on the edge of your abilities sometimes means failing even if it’s the best you can do. Then learning from that and adjusting to rise to the challenge.

It was the same thing I’d experienced in the MBA class. The sweet spot for growth lies just past your comfort zone. That 70-85% range was the executive’s guidepost for being able to positively contribute while leaving room for growth.

The lesson was meant to impart that you want to find yourself in positions where you’re qualified enough, but not overly qualified. Challenged enough, but not overly challenged.

Like Goldilocks, there needs to be the right amount of difficulty.

If everything is too easy, you get comfortable, stagnant, and bored. You accidentally let time go by without any progress in your abilities.

The opposite is true too: being too far over your head leads to burnout, anxiety, and lets down everyone else if you can’t get the job done.

Nat Eliason writes about this as if you’re choosing a poker table to play at:

“You always need to be a little outside your comfort zone if you want to keep learning and improving.

It’s why the “you always want to be the dumbest person in the room” advice is mostly good, but only mostly. It’s great to be the dumbest person in the room so long as you can keep up. Otherwise, you’ll look silly.”

You want to jump into the deep end of the pool, but only if you can tread water.

Ideally you can play games that get harder as you get better. The increasing difficulty naturally keeps you in the 70-85% range even as your skills improve. That constant turnover of challenges prevents complacency from setting in. It forces you to keep learning before you ever get too comfortable.

Startups are the perfect example of the intersection of competence and chaos that foster this kind of growth. Problems are rapidly solved but new challenges appear just as quickly. It’s not possible to stagnate because the changing environment continues to change.

The small teams at startups mean everyone wears lots of hats. Between the Arrived pre-Seed and Series B, I’ve spent time in BizOps, Marketing, Finance, Real Estate Investments, Investor Relations and more1 before finally settling into a Product role.

Each shift knocked me back down to at least the 70% level. Low enough to keep learning fast, but high enough to still make a real impact right away. Rapidly repeating that cycle creates a time warp: every 1-year within a startup is worth at least 2-years of experience at a larger firm.

Parenting has been the same2. Like startups, the pace of new challenges never lets you hit 95%+ competence. Just when we feel like we’ve figured something out, the baby goes through a developmental change and it’s back to the drawing board.

In the parenting world that means handling changing sleep patterns, eating habits, and constantly questioning if a new skin rash is normal.

We’ve had older parents tell us that “it doesn’t get easier, it just gets different”. That perfectly encapsulates what it’s like to live on the edge of your abilities.

One of my biggest fears is blinking and realizing that 10 years have passed without personal or professional growth.

Aging is inevitable. Growth is optional. The only way forward is to deliberately resist what’s easy and choose to do hard things, even if you don’t feel fully ready.

Over time, I’ve learned to recognize what it feels like when my competence in a particular area gets too high. When I get a little too comfortable. When it’s too easy.

When I start to feel like I’m coasting, it’s a signal I’ve stopped growing. That’s when it’s time to take on the next challenge and do something I’m not quite ready for.

I’ve learned to shake it up when something feels too automatic. Stretching into the next arena to push me beyond my comfort zone. Each time I’ve forced myself back down to 70% by jumping into the deep end of a different pool, I’ve come out stronger and more capable on the other side.

It’s been true in parenting, work, and in a literal classroom.

The hospital nurse quietly watched. Then she smirked and told me I had just put my first diaper on backwards.

6-months later, I could set the world record for fastest diaper change. The first six months of fatherhood has been an amazing journey so far filled with challenges, exhaustion, wonder and joy.

Nearly all our friends have asked some variation of “what’s it been like?”. These are a few reflections from early months of fatherhood.

You Adapt Quickly

My dad always told me “Kids don’t come with an instruction manual.” Like any new parents, we’re learning on the fly. Our learning curve has been a vertical line.

Learning on the Fly

We each read several books about pregnancy, birth, and the first days of having a baby at home. We felt good!

But “everyone has a plan until they get punched in the face.1”

Reality is frantically searching Google/ChatGPT for what to do when the baby screamed until 3am on the 1^st night home.

Nobody’s every fully “ready” to become a parent. It was great to learn ahead of time, but parenthood is all “just-in-time” learning. We’ve gone through waves of learning about safe sleep, solid foods, car seats, and sleep schedules. Babies change so damn fast it’s constantly time to learn about the next stage of their development.

I’m slowly coming to the realization that it’ll be like this for the next 17 1/2 years. Constantly adjusting to a growing child and learning whatever is most important for that stage.

Just survive and advance.

Who Even Needs Sleep Anyway?

Speaking of adapting, the way the human body can adjust is incredible. I expected to be a walking zombie for the first year?? I figured we’d feel braindead for the first few months because everyone quips about exhausted new parents are.

Yes, we’re definitely sleep deprived. The first 10 nights were pretty rough. And my wife is amazing and handles every night feed.

Still, 6-months in, our bodies have magically adjusted. A cup of coffee in the morning and I’m good to go (as long as I have a mid-morning cup and another in the afternoon…).

Still, the point is that I’ve felt like I have my normal amount of energy throughout the day despite fewer total hours of sleep and a few interruptions per night.

Parenting is a Team Sport

Sydney and I have strengthened our bond as partners while navigating such a transformative time in our lives.

We’ve built great routines and really found our rhythm as teammates. She feeds the baby while I handle the laundry and the dishes. We take turns watching the baby so the other can go to the gym. We’re constantly communicating about the schedule for the day and working together to make decisions in Bennett’s best interests.

Unfortunately, Every Parenting Cliché is True

For better or worse, every day I feel myself relating to the Progressive commercials about turning into your parents. I’m already parroting old clichés as if I’ve been doing this for years.

They’re so memorable because they’re so true.

The Days Are Long, And The Years Are Short

(Or in our case, the days are long and the 1/2 of a year is short).

The first 10-14 days at home were tough. We slept in 2.5 hour spurts every night. I’d watch the June sunsets at 9pm and feel like I was Will Smith in I Am Legend…just trying to survive the night and make it to dawn.

Time flies by. Looking back, I realize how quick that phase was.

The growth and development of a newborn is so fast. He’s already more than doubled his birth weight. Nearly every day we notice him doing something new as he interacts with the world.

Sydney and I have had several moments where we look at each other and smile. We know these precious moments are fleeting and that we’ll look back and reminisce on these sweet baby memories.

We’ve been reminding ourselves that despite the challenges, we’re living through the “good ‘ol days” right now. We need to live in the moment. He’ll be a teenager before we know it, probably trying to sneak out of the house. Gotta soak it all up before it’s gone forever.

It Takes a Village To Raise a Child

It’s difficult to overstate how much easier the transition to parenthood has been with the community around us. We’re blessed to be living within 20 minutes of both sets of grandparents and have aunts, uncles, cousins, and friends from all stages of our lives nearby.

We didn’t cook a meal for 3 weeks after birth. I had expected to ask folks kind enough to bring us food to leave it at the front door, thinking that we wouldn’t be ready to receive visitors. Instead, the opposite was true. The social interaction brought joy to our day and helped us get through the tougher early days at home.

We’ve had plenty of babysitters ready to watch the baby so Sydney and I can go for a date night, or even just have a few minutes to work out.

The most surprising community aspect has been the relationships that Sydney has formed with the other moms in the area. There’s a group chat of a dozen-plus women, who all gave birth within a few months, constantly lighting up through all hours of the day.

They’ll ask each other for advice, support, and had other moms to hang out with during the day when they were on maternity leave. Having a community of women going through the same first stages of motherhood and figuring things out at the same time has been the number one2 most helpful thing for Sydney.

We know we’re very fortunate to have such great people around to support us. We know we’ll rely on our village over the coming years as we go through different stages of life.

Gratitude

Particularly since Thanksgiving is next week, I’ve been feeling a lot of gratitude. There’s been ups and downs in the first few months, but we’ve successfully navigated each challenge.

Paternity Leave

I’m very thankful to Arrived for making it possible to take 3 months off to bond with Bennett and help care for Sydney. The earliest days were filled with a lot of newness while we tried to find our sea legs.

I was able to use the time off to make things easier while Sydney recovered from birth and established breastfeeding. Laundry, dishes, pet care, and more. It was a point of pride that Sydney only changed ~5% of the diapers over the first 2 weeks.

We were able to take time to bond together as a family. Walks around the neighborhood. Meeting friends for coffee or lunch. We were even able to take Bennett on his first road trips, out to Ellensburg, Bainbridge Island, Victoria, and over to Whidbey Island for a wedding. Along the way we figured out how to install the car seats and found some semblance of a routine at home.

It Could Be A Lot Harder

Particularly during the difficult parts, we keep reminding ourselves that it could all be a lot harder. It helps put things into perspective when we list the added difficulties that would make parenthood more challenging:

• Being a single parent

• Living paycheck to paycheck

• Unable to take any time off work

• Not having medical insurance

• Living in an area without access to health care

• Lack of family and friends to help

It all leads to feeling very grateful and grounds us in perspective when we’re having a tough day.

Women are Amazing

Observing (and participating) in the pregnancy, birth, and post-partum journey has been awe inspiring. It’s amazing what the female body is capable of and how nature works to create new life and bring it into the world. The whole process is a roller coaster of physical, mental, and hormonal changes.

The months of pregnancy, intensity of labor, and the recovery afterward all gave me a new level of respect and admiration for women. I’m forever grateful to Sydney for the hard work she’s done that went into creating our son.

Our Family is Changed Forever

Life has shifted so quickly that our childless days already feel like a lifetime ago. We’re beyond happy and could never imagine going back.

Paternal Love

We love the little guy so much already! Sydney keeps repeating what her parents told her: you think you know how much your parents love you, and then you have a baby of your own and realize how they love you than you could have possibly imagined.

New Family Relationships

We’ve been awed by our new love for him, but it’s been equally rewarding to see how special it is for our friends and family to hold Bennett and get to know him. It’s brought us incredible warmth and joy into our lives to see grandparents, cousins and friends hold and dote on the baby.

This includes seeing our pets (aka trial-babies3) interact with their new family member. Our dog, Salsa, was curious and cautious about the baby in the early days and has shifted into pure love. She licks his face and sniffs him. Now that he’s starting solid foods she sits right next to his high chair to snag any scraps that hit the floor. I keep telling her just wait until he can throw a tennis ball for her.

There are Tradeoffs

And I’m happy to make them. I played less golf this summer. My gym schedule wasn’t consistent for a while. But all the positives of fatherhood have completely outweighed anything else. There’s a lot of things that used to feel important that simply don’t feel that relevant anymore.

On a lighter note, I’m now officially licensed to tell eye-roll-inducing dad jokes. And I swear my grill skills have jumped to the next level now that I have the title of “Dad”.

The Journey is Only Beginning

It feels weird to be writing parenting reflections with such little experience under my belt.

After all, we’re at the very beginning of a lifelong journey as parents. I’m sure my thoughts on parenthood will continue to evolve as Bennett goes through different phases of development and growth.

The best advice we’ve received was to live in the moment and enjoy the now. Don’t get caught looking too far ahead to teaching him to ride a bike, throw a ball, or cheer on the Huskies and Seahawks together.

Those things will come in time. Right now, just enjoy the ride.

I’ve spent the last few years talking to more than 1,000 retail investors.

I’ve talked with investors in 1-on-1 calls, webinars, and happy hours. Even now, if you email our support line the odds are high I’ll see your message.

Startups like Arrived are built on user feedback. Our growth has been fueled by a tight feedback loop between investor insights and product development. Talking to investors helps tremendously with the problem identification and validation work I do now on our product management team.

I’ve learned a lot about retail investors through those conversations.

The term “Retail Investor” might conjure feelings of Wall St Bets speculators, but that’s far from reality.

A retail investor is really anyone investing their own capital. It’s a broad group that spans 22-year old’s in their first job to retirees. Retail investors are incredibly diverse in their age, sophistication, and goals. Their financial decisions are shaped more by their life experiences than financial theory.

Every investor is unique, but themes start to surface when you’ve talked to enough of them. Of course, there is some selection bias. The folks I meet are people who discovered Arrived and were motivated enough to talk. Still, their stories highlight some broader observations about how retail investors think.

Here’s a collection of 7 things I’ve learned from talking to 1,000+ retail investors:

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People Believe in Real Estate

“I’ve always believed real estate was one of the best ways to build wealth. I’ve seen family and friends do well with rentals over the years, but I never had the time to do it myself. When I found Arrived, it finally felt like there was a way to invest in real estate without having to be a landlord.” – Investor from Austin

This was one of the core insights that led to the creation of Arrived.

Gallup polls show real estate is American’s preferred long-term investment. The margin has been growing over the last decade.

Yet only a fraction of people who want to invest in real estate actually do. IRS data shows that just 7% of households own rental properties. There’s others that invest in public REIT’s or private syndications, but not enough to make change the conclusion.

There’s a big gap between the ~7% that own rental properties and the ~60% that own stocks. And this is despite real estate being preferred over stocks!

Retail investors already think real estate is a good investment. It comes from their life experiences. They’ve seen the housing market consistently appreciate, particularly in the last 15 years. Personal experience plays a role too. Some investors reference seeing a brother or an uncle be successful as real estate investors or rental property owners. Those observations fuel the assumption that the asset class is a solid investment.

When I talk to investors, it’s never about the merits of why they should add real estate to their portfolio. Our conversations are always about Arrived: how we operate, what our investment theses are, and what to expect from becoming an investor. My hunch is the platforms for fractional art, collectibles, wine or music royalties investments spend a lot more time educating and pitching the asset class than we do.

Real estate shouldn’t be considered an alternative asset. It’s not an esoteric new asset. Consumers are already looking for real estate to shake up their traditional stock and bond portfolio. Investing in real estate has been around for a long time, but now it’s becoming more accessible to the average consumer.

3 Things Prevent People from Buying Rental Properties Themselves

We know from the Gallup poll that there’s a huge gap between the number of people who think real estate is a good investment, and those who actually invest in real estate.

What holds people back?

It always comes down to time, capital, and expertise. Like a 3-legged stool, there’s going to be an accident if one leg is broken.

Time:

“I loved the idea of owning rentals, but I didn’t want to spend my weekends dealing with tenants and repairs.” – Investor from Cleveland

Nobody wants to get the midnight phone call on a Saturday night asking you to call a plumber about the burst pipe that’s flooding the bathroom.

Acquiring and managing a rental property is a significant time commitment. Investors are wary of making an investment that turns into a job.

Capital:

Buying rental property is expensive. Only a fraction of people interested in buying rental properties have the capital to make the down payment. Even those with the funds to buy an entire rental might not want that much concentration in a single asset.

“Even with some savings, gathering enough for a full down payment in my area just never felt realistic.” – Investor from San Diego

Expertise:

Retail investors are drawn to the asset for its usefulness as an inflation hedge, steady income, appreciation, and favorable tax treatment.

What holds them back is knowing how to develop and execute on a strategy. Finding, financing, and managing rental properties takes specialized knowledge, and the learning curve can be intimidating when so much capital is on the line.

“I knew real estate was a good investment, I just had no idea where to start or how to pick the right property.” – Investor from Baton Rouge

There’s a Shift from Active to Passive Investing

“You know, I’m just trying to find ways to diversify and get out of the headaches of every day landlording.” – Investor from Laguna Beach

“I was looking for similar returns without the hassle. It was a lot of work just to collect rent when it was due every month” – Investor from Tampa Bay

A lot of investors tell me about how they owned rental properties in the past, and are specifically interested in Arrived because it’s passive. They’ve lived the landlord life before. They don’t want to go back.

Current landlords regularly ask if they can 1031 exchange their properties into Arrived in order to leave active management. There are 20.5 million rental properties owned by mom-and-pop landlords. As the Silver Tsunami wave of aging Americans continues over the next decade, expect to see owners feel burnt out of management and look to exit.

Whether they own rental properties now or in the past, there’s a clear shift of investors looking for more passive opportunities.

Building Trust is Everything, and There’s More Than One Way to Do It

Retail investors rely more on trust than spreadsheets. They invest when they believe in the people behind the platform.

Building trust looks different at every stage of growth.

The early adopters who invested in our first properties didn’t have much of a reason to trust us. They saw some early press in Geekwire and were willing to invest a small amount in a novel idea. The first investments were modest, but it was a thrill to see them coming in from people we hadn’t spoken with directly.

Our next phase of trust came through associations. We had a number of notable VC and angel investors in our Series A round, but none more recognizable than Bezos Expeditions, the personal investment company of Jeff Bezos. For about 2-years, I’d hear investors say that Bezos’s (small) involvement was enough for them to feel comfortable taking a chance on a new startup.

As we operated rental properties, we continued to gain trust with our exisiting investors. A common theme was that we did what we said we were going to do. Investors were delighted when we leased a property for more than the initial forecast, and our regular dividend payments reinforced that we were capable operators. Each successful step garnered more goodwill with investors.

Today, our scale builds trust on its own. With more than 500 properties, four years of dividend payments, and starting to sell our initial properties for a profit, investors can see the results for themselves. Our regular webinars allow us to talk to dozens of investors at once, answer their questions, and make sure there’s still a personal touch.

Investors need trust to take the leap of faith and make an investment. There’s no single formula. It comes from consistency, transparency, and delivering on promises over time.

Everyone’s Portfolio Reflects Their Life Experiences

I regularly talk with investors one-on-one and we usually start with their background. What are they currently invested in? Why are they interested in real estate? What are they looking for?

It’s fascinating how open people are.

Each investor is different. They have their own unique story and perspectives. Fears and goals. It’s really interesting to hear different narratives about why people invest the way they do. You can hear the life experiences that directly shape their risk tolerances.

Because of that, they value investment criteria differently. Some care the most about a home’s curb appeal, financial ratios, or the school district rating.

Some investor view dividends as the main reason they’re investing with any appreciation as the cherry on top. Others have the exact opposite approach, where they’re looking for appreciation over time and it’s the dividends that are a bonus.

They also tend to have an affinity for places they’ve been. We often get requests from investors to expand to cities around the US, and they’re typically places that the investor has personally experienced and believes in based on the growth happening in that particular area.

Others are driven by their financial goals. Some love the stability of real estate because they can’t stomach the volatility of stocks. Some look for income-focused returns to supplement their retirement. A few just love investing and adding new alternative assets to their portfolio.

As Arrived has expanded into different types of real estate, it’s become easier for investors to find something that fits their specific objectives.

“I’ve always been heavy in stocks, but the swings lately have been stressing me out. Real estate feels steadier. I get the consistent dividends to lock in some returns and still have some appreciation in the future” – Investor from Boulder

Investors are looking for more than just another REIT

There are easy ways to invest in real estate through a brokerage account, but they fall far short of what most retail investors actually want.

Retail investors want simple, understandable ways to invest in real estate that provides steady cash flow and appreciation. The public REIT’s and real estate funds available via brokerage accounts don’t fit the bill.

Public REITs have been around since the 1960s and give investors some exposure to real estate. Most investors own them indirectly through their index funds and target date funds, but it’s far different than having a meaningful allocation to real estate.

Few investors specifically seek out REITs directly. Those who do often find it difficult to understand what they’re buying. The underlying properties are buried in 10-K filings and quarterly reports, and there’s little transparency into what they actually own.

REITs also behave more like public equities than private real estate. Their prices move with interest rates, sentiment, and broader market swings. Valuations are more reflective of the operating company’s performance than the growth of the real estate itself. Investors aren’t looking for another stock. They want direct exposure to the income and appreciation that real estate provides.

Exisiting options are complex and impersonal. difficult to understand. Investors are craving plain-language, transparent ways to invest in real estate that don’t correlate with public equities.

Real Estate is Quickly Moving Online

Stocks used to be analog too. Over the last 75 years, technology made the stock market significantly more accessible. Phone calls, brokers, and commissions transitioned to seamless brokerage apps.

The same thing is happening with the real estate market.

Most real estate syndications have high minimum investments and require personal connections to access deals. Now there’s several online real estate options to add the same strategies to your portfolio with just a few clicks.

I’ve seen the change firsthand. More investors are comfortable making sizeable investments without talking to someone at Arrived individually. Awareness and comfort with the category is growing.

The shift won’t just be for investments. There’s a lot of innovation happening within the PropTech and FinTech worlds. Expect to see more real estate experiences move online in the next decade.

After talking to more than 1,000 retail investors, I’ve learned how unique each investor each one is. There are similar themes, but no two are exactly alike. Behind every question is genuine curiosity and a reflection of their own goals, fears, and life experiences.

Their needs boil down to the same simple things. They want trust and transparency. They want understandability. They want access to an asset class they believe in and are becoming more comfortable using online platforms to give their hard-earned cash to others to manage.

The future of investing will belong to the companies that truly listen to those needs and build with them in mind.

There’s always more to learn, and I’m looking forward to the next 1,000 conversations.

Disclaimer: The views expressed here are my own and do not necessarily reflect those of Arrived. This article is for informational purposes only and should not be taken as investment advice.

I crack my knuckles every day. Since I was a kid, people would tell me I was doomed for arthritis. There were a few feeble attempts to quit before I gave up and figured arthritis would be a problem for Future Jake.

I brought it up at a recent doctor’s appointment. The doctor chuckled and told me it’s a common misconception. It turns out that’s an old wives’ tale and that several studies that have failed to find a connection between knuckle cracking and arthritis.

So why did I believe my knuckle cracking habit would lead to arthritis?

The answer is strikingly simple: I heard the same thing over and over but never researched it. By merely hearing the information several times (“Cracking your knuckles will give you arthritis!”), I naturally assumed it was true.

My knuckle misconception was no big deal1. But it got me thinking about what else I might falsely believe. Where might I be relying on information that isn’t true? That I only believed because I heard it somewhere? And how exactly was this happening?

How We Learn

One of my favorite books is Thinking in Bets by Annie Duke. A former professional poker player, she goes into depth describing how our lives are a combination of the quality of our decisions and luck.

The root of our decision quality is the information we base those decisions on. Because of that, the book spends considerable time discussing how we learn information and update our beliefs.

Duke eloquently explains the difference between how we think we learn information and how we actually learn it:

“We form beliefs in a haphazard way, believing all sorts of things based just on what we hear out in the world but haven’t researched for ourselves.

This is how we think we form abstract beliefs:

1. We hear something;

2. We think about it and vet it, determining whether it is true or false; only after that

3. We form the belief.

It turns out, though, that we actually form abstract beliefs this way:

1. We hear something;

2. We believe it to be true;

3. Only sometimes, later, if we have the time or the inclination, we think about it vet it, determining whether it is, in fact, true or false.”

1. We hear something;

2. We believe it to be true;

3. Only sometimes, later, if we have the time or the inclination, we think out it and vet it, determining whether it is, in fact, true or false.”

Unsurprisingly, our brain works like this because of evolution. It was advantageous for our ancestors to accept new information as true to make faster decisions while expending less energy. If there was rustling in the bush, assuming it’s a predator was safer than waiting for confirmation.

We used to accept new information as fact by default because we only learned from our own experiences and from interactions with the trusted confidants in our tribe. As we developed language and communicated with a wider range of people, our brain kept the same pattern of experience-something, accept-as-true, question-later-maybe.

That process resulted in greater odds for survival and reproduction and were eventually passed down to modern humans.

To make matters worse, it’s hard to reverse.

It takes extra energy to think back to a past fact, reconsider why we know it, and then override the information if necessary. Because it takes extra energy, we only do it if we really must.

“Wanna bet?” is the example that Duke uses as a trigger to force your brain through Step 3 in the quote above. The prospect of losing money forces you to take a step back and evaluate what you know, why you think it’s true, and how confident you are. Without a nudge, we’re content to accept what we hear as fact without vetting it.

That’s the root of why I believed knuckle cracking would lead to arthritis. I heard it mentioned several times. Accepted it as true by default. I never had a reason to challenge or reconsider it and went years with a false belief before I updated my information.

Living With Our Modern Brain

Our brains are virtually the same as they were 100,000 years ago. The rest of the world has changed a little bit over that period. The shortcuts that helped us survive in a hunter-gatherer world can cause chaos today.

We accept things as true by default, we rarely re-evaluate something we’ve heard, and we’re hard pressed to update our beliefs. Not particularly helpful!

These days, we’re no longer getting information solely from our own experiences and members of a tight knit tribe. We’re flooded with headlines, social media posts, and now AI outputs that have their fair share of hallucinations.

Today’s world of constant information bombardment means the way we learn information can be deceptively dangerous.

To make matters worse, our brain also naturally prefers to listen to opinions that agree with our priors instead of ones that challenge us. Algorithmic feeds create echo chambers that exacerbate this.

Unfortunately, we can’t rewire how our brains work. Unless there’s a reason to challenge new information, it just seeps into our heads and is absorbed as fact.

The best thing we can do is be wary that’s how our brains work and be extra cautious when we rely on things “we think we heard” somewhere.

Most decisions in a day aren’t particularly important. But when major decisions come up, it’s worth slowing down and examining the assumptions behind them.

Take a pause. Crack your knuckles.

What information are you using to make the decision?

Do you think it’s true? Where did you hear it from? How confident are you?

With the way our brains work, be careful about those things you know for sure that might not be so.

Would you “Wanna bet?” based on it?

I’m generally a happy guy. My default state is positive and upbeat.

There are two scenarios where this isn’t true:

1. I’m hungry

2. I haven’t exercised recently

The antidotes to both are so simple: eat and workout. Without them, friends and family have seen me turn into a hangry nightmare.

Consistent weightlifting was the backbone of my exercise routine, with yoga, golf, and running all sprinkled in.

Then we had a baby. Routine went out the window. Goodbye consistency.

My workout habits cratered when faced with a newborn with no circadian rhythm.

The first few weeks were jam-packed with clinging to the new parent learning curve with our fingernails. There was no hope of consistent exercise beyond neighborhood walks.

Even as our sleep improved and we felt more confident in how to care for our baby, I didn’t get back into my exercise habits. I’d fallen off the wagon. Getting back to work after paternity leave left even less available time in the day.

During limited stretches of free time, I’d feel the responsibility to catch up on everything else: respond to that email, make that appointment, run that errand. The dishes and laundry are constantly calling. But by trying to always take on more, I neglected to move my body.

For the first time since I was 15, I started to have regular stretches of 3-5 days between workouts. I wasn’t feeling like myself. Lethargic. No patience. Molehills becoming unconquerable mountains. I was in a funk.

The occasional workout wasn’t cutting it. Sydney regularly encouraged me to do a 30-minute Peloton ride, and if I fought the lethargy enough to listen to her, I’d instantly feel better. Yet I’d make the same mistake again and go another 4-days before the next workout.

During one exercise-less day, I had my 6^th cup of coffee and realized I was never going to fix my cloudy head with caffeine alone. I needed sweat.

I sat down and got organized every evening. By waking up with a plan for when and how I’d workout that day, I became more consistent at following through. Our situation would necessitate some flexibility, but if I didn’t have any plan then the day would accidentally pass me by.

It was all an exercise (pun intended) in adjusting. Pushing some projects and chores to another day for the sake of making sure I got that workout in. And I began to figure out how to sneak in exercise with the baby in tow. We’ve loved lifting weights together in the garage and going for a quick jog. A short uphill hike with an 18-pound baby gets a good sweat going quickly too.

Like most people, exercise hits my reset button faster than anything else. It brings an instant energy boost and improved mood that carries through the rest of the day. As I strung together consecutive days of exercise, my upbeat demeanor returned.

It’s simple. It’s dumb. It’s perfect. Exercise regularly and don’t let me get too hungry. That’s all it takes.

I’ve realized that in order to show up as the best husband, father, and friend I can be, I need to regularly exercise to recharge my own batteries. I had been sacrificing workouts for the sake of being able to help with childcare and the constant to-do list around the house. A noble goal, but a system that wouldn’t be sustainable. You can’t pour from an empty cup.

I’m focused on re-building my exercise habits and adapting as necessary for our new lifestyle as parents. There’s only 1 fitness goal I have right now: sweat every day. It doesn’t matter how long or what type of exercise.

Predictably, I feel much better after stringing together several days with a sweat. My energy is better, my head clearer, my focus stronger. I feel like I can take on the world.

If I’m ever rude to you, I apologize. Odds are I just need a bite to eat and a quick sweat.

Since 2021, Arrived has been a platform where you can buy shares of individual rental properties.

Since August, Arrived has been a platform where you can sell shares of individual properties.

Access to liquidity was our #1 request from investors. Over the past year, our team worked hard to build out a full secondary market with a user experience that closely resembles a stock trading platform.

Our investors are excited about trading on what’s already the largest platform for buying and selling shares of rental properties, with 400 properties across more than 60 cities.

But more importantly, our investors can finally have some peace of mind.

Last summer, I talked to an investor named Kevin1. Over a 15-month period, he had invested over $30,000 into Arrived properties.

Then he stopped.

Why?

He simply hit the limit of what he was willing to allocate into an illiquid investment where he had no control over operations or ability to exit.

He still liked us! He was happy with his investment results! He didn’t want to sell his shares!

But even with an investor singing our praises, we wouldn’t be able to count on him for additional investment until he had a way to sell – just in case he ever needed it.

Some Quick Background

Each Arrived property is purchased within an LLC. That LLC is fractionalized in a process with the Securities and Exchange Commission. The result is that anyone in the US can buy shares of the LLC, which entitles them to a pro-rata share of the cash flow from renting the property out, as well as any appreciation when the underlying property is eventually sold.

Our offering circular clearly states that we’re aiming to hold our long-term residential properties 5-7 years before looking to sell and that Arrived has full managerial control over that decision (and ability to sell reasonably before or after that 5-7 year window depending on market conditions).

Even with the stated lockup, we felt the product-market fit from our first property launch. The first 6 rental properties were fully funded within three weeks. For much of 2021 and 2022, we simply couldn’t acquire properties and receive SEC qualification on each fast enough to meet investor demand.

Investors wanted access to residential real estate investments they could understand and were OK to trust Arrived to manage the dispositions at some nebulous time in the future.

In hindsight, it’s incredible that we funded ~400 properties without the ability to liquidate.

Importance of Liquidity

However, we knew that a lack of liquidity was going to slow us down eventually.

While I was on our weekly webinars, I’d caution investors not to overcommit.

“Think of the Arrived properties as being similar to making 401(k) or IRA contributions. When you contribute to a retirement account, you KNOW those funds aren’t going to be accessible in the short term. Don’t invest anything you might want or need to use in the short term because there isn’t a way to get the money out of the investment until we sell the home in several years.”

I was spelling out what’s obvious to any sharp investor: liquidity is an important consideration when evaluating an investment. Knowing your options for getting out is critical for cash planning and risk management. Investing in illiquid assets is totally fine (and often necessary for higher returns), but liquidity does play a factor when looking at asset allocations.

This was the right way to set expectations with investors but was obviously going to hamper our growth in the long run. If every new investor was bound to eventually hit their own mental maximum they were willing to invest in our illiquid shares, we’d be artificially constraining our own growth.

We’d already done the hard part! We successfully found potential investors, educated them, provided a good investment experience and strong returns!

And yet the lack of liquidity for peace of mind and “just in case” was going to prevent investors like Kevin from continuing to grow their portfolio with us.

Without offering the ability to liquidate, we’d be building an investment platform with one hand tied behind our back.

So, we casually built an entire Secondary Market

Our goal was to build a secondary market that would enable investors to have confidence that they could sell their shares for a reasonable value if they wanted to exit a position.

The key words there are “reasonable value”.

The secondary market brings buyers and sellers together to determine a market price for the shares independently.

We could build a trading platform system, but if sellers listed their shares and found no interested buyers, it wouldn’t be fair to really say we had liquidity.

Having a market of 400 thinly traded offerings would barely be better than having no market at all.

If sellers needed to take comically large discounts in order to sell their shares, we wouldn’t be providing the peace of mind for investors like Kevin that they’d be able to exit in the future if they needed.

Familiarity Fuels Adoption

We’d need enough participation from buyers and sellers for reasonable market prices to emerge.

But the secondary market is a huge new feature that was going to have a bit of a learning curve to it. It’s inherently a much more complex product. Investors suddenly have hundreds of investments to analyze at once and need to pick the specific price they want to place an order at. There’s no guarantee that a buy or sell order would match with someone on the other side of the transaction.

Our best at having fast and broad adoption across investors would be to design the market to be as similar as possible to what investors are used to when trading on Fidelity, E-Trade, Schwab, and other online brokerages. Since our shares would have far less trading volume than any stock, we also looked at other types of markets where investors review an order book to price their trade. This included platforms like StockX, Kalshi, Rally, and Stubhub.

If investors were familiar with the UI, there’d be faster adoption, leading to more participants, which would lead to better liquidity in the whole system, drawing in more investors.

A beautiful virtuous cycle.

On top of our UI, we made several decisions about how the market functions to mirror the stock market.

Like the stock market, investors place limit orders for a specific property. Investors can place buy or sell orders and see the full order book and recent trades. Orders can be placed at any time during the week, including evenings and weekends, but the shares will only transact during trading hours of 9:30-5pm EST.

The biggest difference is that the Arrived Secondary Market is only open for specific trading windows, rather year-round

Market Participants

While Kevin wasn’t interested in actively trading on the secondary market right now, there’s a ton of investors who would be.

There’s very obviously two groups of investors who will benefit immediately from the market’s existence: buyers & sellers!

Buyers

Ahead of the market launch, we talked to investors looking to buy. They typically fell into two camps: A Bargain Hunter or a Collector.

Bargain Hunter’s told us they’d be opportunistic. They were excited by the prospect of snatching up shares from sellers willing to sell at a discount to the current value. To them, almost nothing else mattered about the specifics of the property. These are exactly the type of investors you want in a secondary market because they’d help set a floor for pricing and bid shares up toward a reasonable value.

Collectors are classic Arrived investors. They love that they can buy into different rental homes in different markets across the country. While we have hundreds properties overall, we typically only have 2-5 available at any given moment. Investors may have missed the opportunity to invest in properties in certain markets or properties with certain characteristics (e.g. homes with leverage). Collectors will have an opportunity to essentially shop the back catalogue of Arrived investments to add to their portfolio.

Sellers

Similarly, sellers tend to come in two flavors as well.

The first is the Bolter. Bolters tend to be investors who have decided that we simply aren’t the right investment for them. Some churn is natural for any product. While investors aren’t required to keep making new investments, there hadn’t yet been a way for them to be able to sell the exisiting shares that they already owned.

The more interesting type of seller is the Strategist. These are sharp investors that would be watching the market for opportunity. It may be selling shares they own to take profits and lock in capital gains. It could be re-allocating funds across their Arrived holdings or their overall portfolio allocation. And it could be investors being strategic with the other things in life they need to finance such as a down payment or a child’s college tuition.

Looking Forward

This was no small feat!

Both to nail the technical delivery, but also to intersect with various securities laws and deliver a delightful user experience despite the increased complexity of the product.

Our team dug all the way through the fun details around funding flows, third-party integrations, REIT compliance, investor education, and putting reasonable guardrails in place to limit potential issues.

As a finance nerd, this was a phenomenally fun project to work on. It was quite a challenge to build a marketplace that operates like stock market while adjusting for all the nuances that make our asset class and product unique.

There’s still some obvious limitations of the market: It’s only open intermittently, shares may trade below their current net asset value, and there are transaction fees that will eat into the returns. Still, for a real estate based investment it’s pretty damn liquid.

This is an incredibly novel product. I’m incredibly proud of the whole team for the work over the past year to take this from a general idea into a tightly scoped and well engineered final product.

Now that we’ve unlocked a sell option, it’s time to start iterating. The marketplace will continue to grow as we acquire new properties. As we’ve run 3 different secondary market weeks, we’ve started to gather a ton of feedback from investors on how to improve the trading experience. Most importantly, we want to continue to provide peace of mind for all investors by ensuring there is an active marketplace where they can access liquidity if and when they need it.

Most importantly, we want to continue to highlight the activity on our new marketplace. After all, we built a secondary market to provide peace of mind for all investors by ensuring they can access liquidity if they need it. Removing that hurdle means that investors like Kevin can confidently continue to add real estate to their investment portfolio.

Disclaimer: The views expressed here are my own and do not necessarily reflect those of Arrived. This article is for informational purposes only and should not be taken as investment advice.

The other month I met someone who doesn’t have a cell phone. Never has. Blew my mind. In the year 2025, how on earth could someone possibly function without a cell phone of any kind?

“I don’t know” he told me. “Just haven’t needed one”.

Keep in mind, this is not a retiree hanging out on a golf course every day. This was a practicing attorney.

This tech luddite. Part of only 2% (!!) of Americans who don’t own a cell phone.

My mind spun a bit as it sunk in how much of life revolves around having a cell phone.

Texting and phone calls, duh.

But what about calling an Uber?
Directions?
Listening to music?
Taking pictures?
Using Google to search for anything on the go?
Entertainment via social media or YouTube?
Two-factor authentication into what feels like every website these days?

My, the world has changed in the ~18 years since I got my first cell phone. They’re critical to modern life! How could this guy function?

He said he’s up to date on his email and has a home phone with a voicemail he checks regularly. Simply hasn’t needed one.

He went on to tell me that he didn’t want anyone in the world to be able to be able to contact him at a moment’s notice.

Besides, why open himself up to all the other distractions that comes with being constantly tethered to the internet? The little thing in your pocket means constant temptation to look at email, news, social media, and anything else that could pull him out of focus on what he’s doing.

After the shock wore off, I started to realize his point.

As someone who always has their phone within arms reach, it hit home. Modern phones are masters of sucking you in. Particularly as a new parent, my free time is strained like never before.

I want to start being more intentional with my time. Periods where I can sit and fully focus on one thing are too fleeting to leave open the possibility of distraction.

So, I’m trying something new. I’ve started to leave my phone downstairs while I focus in my office upstairs. For the first few days I felt myself reach into my pocket for a phantom limb. Old habits die hard.

But already, I’m finding longer stretches of deep focus. Work feels less fractured. Short breaks feel more restful without the time being crammed with notifications and scrolling.

I’m not giving up my phone and becoming a monk quite yet. But I am starting to think that maybe that lawyer was on to something.

Once again, I’m sitting down to start a new writing habit.

I’ve tried this a few times before.

In 2020, during the height of COVID lockdowns, I bought my own URL and started writing. I made it through five published posts before the world re-opened and I was distracted by the return to in-person activities.

I tried again this past January as a New Years Resolution. I opened a word doc and committed to journaling something in it for 30 straight days. I hit that goal but faded after Day 73 as preparations for our new baby ramped up.

Now, yet again, I’m hoping to start and have it stick.

Why do I insist on coming back to writing?

Writing is Thinking

Writing forces clarity and specifics. The process of writing helps to clean the thoughts in your head. Our thoughts feel fully reasoned, but the actual act of putting pen (finger) to paper (keyboard) brings out how messy those thoughts in our head are.

Morgan Housel spells it out more eloquently in his piece Why Everyone Should Write :

“Writing crystallizes ideas in ways thinking on its own will never accomplish.”

Writing forces you to get out of your own head. Our internal dialogue has miscellaneous thoughts floating around that a reader can’t access. Writing makes you focus on the information that’s actually important and organize it in a coherent way.

We often think we have a clear thought and don’t realize how messy it is until we write it down.

Jeff Bezos famously required executives to start meetings with written six-pager memos.

“When you have to write in complete sentences with narrative structure, it's hard to hide sloppy thinking. It forces the author to be at their best. You're getting their best thinking.”

Surface Area for Luck

I believe that writing online will increase the surface area for luck in my life.

We don’t typically appreciate:

1. The degree to which luck influences our lives

2. You can help luck help you

I’ve seen a dozen stories play out that are some variation of:

1. Person showcases something creative online

2. It reaches someone outside their immediate network

3. An opportunity comes from that new connection

The key is that #3 only happens but for #1. It’s an opportunity that wouldn’t happen otherwise.

That begs the natural question – what opportunities am I looking for?

I don’t know. The outcomes are unpredictable. That’s what makes this a reason I’m interested in writing; by sharing what I’m learning, thinking, and exploring, I hope to open the doors to people, ideas, and opportunities that I couldn’t have planned for otherwise.

We can’t predict which connections will matter or what paths they’ll open. And because of that uncertainty, there’s real value in simply putting things out into the world and opening ourselves up to the possibility of letting the unpredictable happen (e.g. getting lucky).

Exploring Intersecting Interests

This won’t be a blog focused on one specific topic. I want to use it as an opportunity to explore different fields, share what I’m learning and working on, and solidify my knowledge and opinions. The only commonality is that it’s interesting to me at the time.

I want to follow my intellectual curiosities and see where they take me. I’m interested in topics across tech, politics, startups, real estate, sports, media, finance, psychology, and societal trends.

I’m a firm believer that the most valuable insights come from drawing connections across disciplines. The world doesn’t work in silos, and often there’s similarities and inspiration found by cross-pollinating ideas from different realms.

The books in my office are filled with notes scribbled in the margins with references to ideas from books in other fields. Writing will be a way for me to expand on those notes and explore my curiosities.

Regret Minimization

Something inside me keeps bringing me back to this. I regret not having kept up prior attempts. I can’t help but think about how much better I’d be if I’d published regularly since my first post in 2020.

It feels important that a voice in my head keeps saying “you should do this” combined with the regret over having NOT done it in the past.

I’m taking it as a signal that this is something that is important to me, even if I can’t fully describe why.

Thus, I’m going to commit to writing regularly for peace of mind, so that in five years I don’t look back and once again regret not writing regularly.

This is basically a Regret Minimization decision. Jeff Bezos popularized this as a framework for decision making. In a 1999 interview with 60 Minutes, he explained how he decided to leave his highly paid Wall Street job to trek across the country and start Amazon:

“When I'm 80… I want to have minimized the number of regrets I have. I knew that when I was 80 I was not going to regret having tried this… but I knew the one thing I might regret is not ever having tried.”

(The video clip of a much younger and much nerdier Bezos is awesome)

I’d rather make the mistake of trying and realizing it’s not for me than keep making the mistake of not trying at all. To paraphrase Coach John Wooden, I’m looking for the self-satisfaction that I’ve given writing my best effort, regardless of how it turns out.

I’d love if you wanted to follow me on the journey by subscribing to this Substack. I’m not quite sure how often I’ll post, what I’ll write about, or how long they’ll be.

If you agree/disagree with anything that I write I’d love to hear from you! Part of this exercise is to sharpen my thinking and my writing, and I welcome any feedback on the writing or further discussion of the content.

Thanks for reading. I’m excited to see where this newfound hobby leads.

A few related blog posts that inspired me to get started:

• The Great Online Game

• Why You Should Start a Blog Right Now

• How to Start a Blog that Changes Your Life

• Why and How to Write Things on the Internet