When I worked for HP, I typically had 4-8 meetings a day. It was a lot! Then, when I left, it dropped off dramatically - sometimes zero meetings in a week. But, as I’m growing my company, I’m holding more and more meetings. Yet, this time round, it feels different. And part of it has to do with this quote from the book Traction:
What makes for great meetings is solving problems. Patrick Lencioni says it best: “Your meetings should be passionate, intense, exhausting, and never boring.” (p. 190)
There were times when my HP meetings were forgettable, dull, draining, and boring. They were typically larger group updates. I’m sure they were great for some people, but I loathed them. HP would hold quarterly all-company meetings, and I usually only stayed on for the first 10 minutes (if not skipping it entirely and only reading the follow-up email).
And yet, I had other multi-hour-long meetings that I loved. Those were the ones where we tackled tough forecasting problems. Or, sometimes it was finding yet another way to say people were printing less (“printing growth is attenuating” was my favorite).
But today, I enjoy most of my meetings. I find many of them directionally similar to what Lencioni described. I had a meeting with the executive director of Love INC to discuss a proposed budget change that wasn’t explicitly addressed in the financial policy document. She wanted my interpretation (as the treasurer) of the policy’s spirit and assistance in updating the relevant section to clarify its application in this situation.
You’d think that would be a horribly tedious meeting, but I enjoyed it. Why?
Rat Race Meetings
One reason people hate meetings is the lack of autonomy.
There’s a neuroscience study called “The Effects of Voluntary, Involuntary, and Forced Exercises on Brain Function after Cerebral Ischemia,” which looked at two groups of rats. In one group of rats, they ran on a wheel whenever they wanted. In the second group, they were forced to run on a treadmill. Both groups ran the same amount. So you’d think, physically speaking, they would have similar effects.
But no.
The voluntary runners had higher hippocampal BDNF (a brain health marker), better motor recovery, and lower stress hormone (corticosterone) levels.
The forced runners showed higher corticosterone (stress) and lower BDNF, with poorer recovery outcomes, typical of chronic stress exposure.
Yikes!
No matter how amazing a meeting might be, if you’re “forced” to go (by, say, a manager), there are built-in negative headwinds. And let’s be honest, most meetings are middling, so in reality, they’re a net negative.
And unfortunately, the person who called the meeting — usually the manager — was the voluntary runner and, therefore, enjoyed it.
I think this explains why I enjoyed my financial policy meeting: I volunteered to join the board. So, even nit-picky policy meetings like that are fun. But I think there’s more to it than just autonomy.
Asymmetric Meetings
Many times, the outcomes are asymmetric. I remember once complaining to my HP boss that our weekly update meeting felt like a waste of time for me (except for my 5-10 minute part, of course). I appreciated her response, “Well, the meeting isn’t for you; it’s for me. By doing it this way, I can get updates from the entire team in a single one-hour meeting instead of holding 7 half-hour meetings. It’s not perfect, but it lets me spend an extra two and a half hours each week tackling other problems. Feel free to multitask when it’s not your turn.”
I think we attend many meetings where the benefits are much greater for the leader than for the attendee. Fundamentally, you have to care about the outcome, or the meeting will feel like a waste of time.
Type II Meetings
Perhaps one way to think of meetings is using the three different types of fun framework. In the same way that there are three types of fun, I think there are three types of meetings.
Type I Meetings:
These are enjoyable in the moment. They might be quick (who doesn’t love it when a meeting ends early?!), energetic, or insightful. I think of meeting someone new for coffee as a perfect example.
Type II Meetings:
These meetings aren’t necessarily fun while in the meeting, but are fun in retrospect. These meetings are what Patrick Lencioni is referring to. You’re solving a problem. Some examples are strategy sessions or negotiations. I find myself wanting to have more of these types of meetings.
Type III Meetings:
These are the worst. They’re not enjoyable during or after. There’s no progress, insight, or closure — it’s just a soul-sucking slog. Ugh! I think group update meetings can get this way if you’re not careful. So can meetings that turn into a one-person monologue, or where the leader is unprepared.
My multi-hour forecasting meetings and that finance meeting were type II meetings - hard in the moment, but fun in retrospect.
Predictable Meetings
In the book Hooked, Nir Eyal explains that “Experiences with finite variability become less engaging because they eventually become predictable” (p. 127). If you’ve ever binge-watched a pre-streaming-era TV show, you notice the show’s pattern, and it quickly becomes predictable and less interesting.
But there’s nuance. Simply changing up the format probably won’t work because only the leader has true autonomy. Eyal continues:
Remember, variability is only engaging when the user maintains a sense of autonomy. People will stand in line for hours to ride the twists and turns of a roller coaster but are panic stricken when they experience a bit of turbulence on an airline flight. Therefore, the job of companies operating in conditions of inherent variability is to give users what they desperately crave in conditions of low control—a sense of agency. (p. 129).
Instead, you want the content of the meeting to be variable. This is probably why weekly team update meetings are the worst: they’re highly repetitive, predictable, and forced.
In my company, I avoid group check-ins and instead do one-on-ones. And, for the most part, I let the other person drive the discussion because I’m already interested in what they’re doing. It’s my small attempt at sharing autonomy. Yes, I’m in four times as many meetings versus doing it as a group, but I find the experience is better for everyone.
And, of course, if you change up the order or topics, some people will enjoy it and others won’t. You’ll never have everyone fully on board unless it’s something where everyone volunteered to attend.
Less Meetings
Another way to limit meeting predictability is to reduce the number of meetings. Here’s the advice from the folks at 37Signals, who only hold meetings as a last resort. In their book Remote, they write:
Meetings. Ah, meetings. Know anyone out there who wishes they had more meetings? We don’t either. Why is that? Meetings should be great—they’re opportunities for a group of people sitting together around a table to directly communicate. That should be a good thing. And it is, but only if treated as a rare delicacy.
When meetings are the norm, the first resort, the go-to tool to discuss, debate, and solve every problem, they become overused and we grow numb to the outcome. Meetings should be like salt—sprinkled carefully to enhance a dish, not poured recklessly over every forkful. Too much salt destroys a dish. Too many meetings can destroy morale and motivation. (pp. 114-115)
They also recommend hiring only smart people who get things done. I mean, obviously, that’s what you want to do, but it’s much harder to do in practice, so the advice isn’t super helpful. “Just have fewer meetings” can also sound like a great theory that’s hard in practice, especially if the alternative is sending more emails. Still, it’s worth remembering and striving for fewer meetings if possible.
Better Meetings
Alright, let’s land this plane. Here’s how I try to make meetings better.
If you lead meetings...
Recognize that everyone else will be walking in with the negative consequence of being a “forced attendee.” You don’t need to apologize; just do the work ahead of time to make the meeting meaningful.
Hold fewer group updates. Go asynchronous or default to 1-on-1s.
Focus your meetings on solving meaningful problems.
End with a “meeting rating” (1–10) to improve feedback loops. I don’t do this often, but I’m trying out Slido.
If you attend meetings...
Find your autonomy: suggest time slots (I blocked out maker hours in Outlook when at HP), ask for the agenda, or volunteer for a meaningful role (like capturing action items).
When possible, choose meetings where you solve problems that you care about. It may not be fun in the moment, but in retrospect, you’ll appreciate them. If you don’t care about the problem, consider not going.
If you’re in a group update, give yourself guilt-free permission not to be 100% engaged because the meeting isn’t for you.
If possible, earn yourself positions where you get to decide if there’s a meeting or not.
Passionate. Intense. Exhausting. Never boring. Meaningful meetings aren’t effortless — they’re earned. Keeping these points in mind can dramatically improve your meeting experience.
This will not be one of those "How I went from 200 views to millions of views" posts. It's quite the opposite because I have a content problem, and I don't know how to solve it.
In my business, the big question I must answer is: "What would it take for someone who found me online to invest $50,000 into a real estate deal with me?" The high-level answer is that I need to create enough trust that I'll do what I say I'll do.
What I'm Doing
My current strategy for building enough trust for that type of investment is a content funnel:
I create podcast episodes and videos to earn trust and attract potential investors.
From those, they visit my website and either download a free due diligence guide or join my mailing list.
That puts them on my email, where I educate them on passive investing & nurture the relationship.
And ideally, they eventually invest with me once I build know, like, and trust.
On a typical week, I produce one podcast, three shorts/reels (from the podcast), and a summary carousel (of the podcast). This is sustainable for me (and Jessi).
My Results
Here are my typical stats:
Podcast audio listens: 10
Podcast video views: 532
YouTube views per short: 1,991
Instagram views per reel / carousel: 215 / 65
LinkedIn views per podcast post / short / carousel: 23 / 7 / 41
Weekly website visits: 62
Email subscribers: 1-ish every 3 weeks
Active investors who found me online: 0
At first glance, those numbers feel... underwhelming. I recognize that subscribers and views are vanity metrics and not my ultimate goal, but they're part of my funnel and feel low.
How Do I Improve?
I have an existing set of investors, which is fantastic, but I'd like to 10X that so we can do more/bigger deals. And for now, my biggest issue in reaching that goal is not having enough people at the top of the funnel. So, I'd like to 10X (or 100X?) each of those results above.
But I'm genuinely at a loss for what I need to improve. Here's an overwhelming list of questions I regularly ask myself:
I've created my ideal customer profile based on current investors. Maybe I need to be more niche?
I've taken classes to improve my video editing skills, but perhaps I need to increase the production quality significantly?
I've gotten help with my YouTube SEO, but the impact isn't meaningful.
I think the topics we discuss are relevant to investors... but maybe not?
Maybe I should do epic real estate things (i.e., hard to replicate at home) and share them?
Should I start or join an engagement pod where 4-10 of us like/comment on each other's posts to kickstart the ol' algorithms to promote them more? (probably not)
Or, should I leave my $1.80 by commenting on 90 posts a day?
I'm posting 1 video and 3 shorts a week. Should I increase to 1-2 a day? Is that sustainable?
I like my titles and thumbnails, but perhaps they're not effective?
Do I need to invest more time in understanding my retention analytics and optimizing what I have?
Should I hire a social media guru? Probably not... But maybe there are folks who could coach me?
Is this answer "yes" to all of them?!
So many questions! And yet, I simultaneously feel like I'm overthinking this!
What Would You Do?
The standard advice is to keep going and improve something 1% each time. I feel like that's what I'm doing, but... I don't know... It's discouraging. I'd like to try putting in 10X the effort, but a) I'm not sure where to put it, and b) I don't have that much time (or money to pay someone else to put in that much time) since this isn't directly related to my revenue.
In reality, if I attracted one qualified investor a month, that would be amazing! So, I don't need a huge following, but having more would be helpful.
So that's where I'm at. I'm open to feedback or ideas. :)
I've been thinking about the new Snow White movie recently. In my opinion, all remakes struggle because they have to contend with the nostalgia of the first version. The movie can't just be a little better; it has to be orders of magnitude better (like Christopher Nolan's Batman trilogy).
Instead, I think the winning strategy is to tell an adjacent story.
For example, Maleficent, Wicked, and Cruella are the origin stories of Sleeping Beauty, The Wizard of Oz, and 101 Dalmatians. It lets the original stand as-is and builds depth into the villain (while often flipping the original's moral framing).
There are also origin stories of side characters:
Finding Dory
Minions
Lightyear
And then there are spin-offs:
The Lego Batman Movie
Venom
Planes
Frasier
These tend to be more lighthearted, which is fine with me.
One obvious concept for Snow White would be the origin story of Queen Grimhilde (aka The Evil Queen). It would follow her journey from royal bride to feared sorceress. Maybe she descends into madness after being betrayed (another moral framing flip). Perhaps her enchanted mirror becomes her only confidant, but ultimately her tormentor. I'd call it "Mirror, Mirror" or something catchy like that.
I'm in! Who doesn't love a well-told anti-hero movie these days?!
The Seven Dwarves
However, one fascinating area to explore is the seven dwarves.
For example, you could go gritty:
Before they met Snow White, they escaped a brutal war in the mountain kingdoms. They were once proud gemcrafters to royalty, but now they live in exile. And they were part of a sprawling underground civilization before the war. Perhaps the gems aren't just pretty but store magic (that was ultimately used in the war). This "band of brothers" swore never to get involved in "human affairs" again... until Snow White.
But I think you could also tell a super fun origin story.
Hear me out: what if they were former thieves?!
Doc is a genius strategist with alchemical skills, but society has rejected him because of a massive mistake. (I know it's vague, but let's keep rolling.)
So, he wants to break into the castle's enchanted vault to steal the Heartstone — a magical gem powerful enough to keep someone eternally youthful and powerful — to change how he looks and effectively create a new identity (it's a selfish reason).
But there's a catch: the only time the vault is being predictably opened is for a wedding ceremony of the King's new wife. His wife died during childbirth, and he found a new wife/stepmother. Unbeknownst to all, she's only marrying to get access to the Heartstone.
To pull off the heist, he gathers six outcast minors.
Grumpy: A no-nonsense bruiser, former royal guard
Happy: A charming con man with a winning smile
Sleepy: Has prophetic dreams, but is unreliable
Sneezy: Can literally sniff out magic traps
Bashful: Quiet and stealthy
Dopey: Silent, but brilliant with gadgets and explosives. A wild card.
I'm making this up without a complete storyline; don't get upset at me.
Act 1 would be recruiting and planning.
Doc has been out of the game until he hears about the Queen's vault. He gathers the old crew - each one reluctant, hiding in exile, or eking out a mundane life. He promises each of them a redo in life because of the stone.
Act 2 would be the setup and challenges.
They do training and recon missions. There are magical hiccups, run-ins with guards, unstable tunnels, and enchanted traps. They discover the magic mirror sees everything, so they must blind it to their actions.
Act 3 would be the heist.
It's a multi-layered plan with parallel timelines. Perhaps Bashful almost sells them out but decides not to. Or, the entire time, Dopey has been accidentally solving problems, but now he deliberately saves the day!
But then they decide NOT to keep the gem and use it to save the newborn princess's life (which, unknown to them, was threatened by the soon-to-be-queen). And an obvious side effect is that it turns her skin as white as snow while protecting her from the Queen trying to kill her in the future (hence the huntsman and the "sleeping death" in the cartoon).
Ultimately, we see them vanish into the woods without rewards, titles, or a redo. But they're content with their decision and start whistling as they go away...
I think some fun titles could be:
Seven and the Stone
Once Upon a Heist
The Seven
That's my idea. Disney, you can DM me for where to send the royalty check. ;)
I hate to admit it, but streaks—consecutive days of doing something—work on me. And if I’m really candid, most of the time, the loss of breaking a streak is slightly more motivating than the positive feelings I get from seeing a long streak.
A Streak For Streak’s Sake
For example, I currently have a 192-day streak of using Duolingo (language learning).
That’s cool, but I actually think I’m over it. We’re back from Spain, and it doesn’t look like I’m going to Mexico this year. So, my motivation to keep going is relatively low. I know it’s probably good for me to keep going, but if it weren’t for that 192, I would have stopped two weeks ago!
How crazy powerful is that?!
For The Love Of It
But there are others that I genuinely enjoy doing every day, regardless of the streak counter. For example, DayOne (journaling), Readwise (book highlights), and MyFitnessPal (calorie tracking).
But here’s what’s interesting: these allow for catching up, and I do that occasionally. And it’s not because I want to ensure I journal or get the review - it’s simply to keep the streak alive!
Broken Dreams... I mean... Streaks
And then there are others that I wish I still had a streak in but no longer do, like Quip (teeth brushing) and Fitbod (strength training). Here are the streaks I had in January (when I originally conceived of this post).
Alas, quip connects to my toothbrush via Bluetooth, and it couldn’t handle the time change in Spain. So, on one day, I have 3 brushings, and on another, I only have one brushing. The steak is broken, and there’s no way to “fix it.”
Does it count that I physically did the responsible thing and brushed twice daily in real life? Nope!
And then there’s these sad situations.
Twenty-three weeks was pretty good, but I got sick after returning from our trip. Combine it with bad weather, and well, the streak is broken. I totally own this one, and I don’t even have the satisfaction of knowing in my heart I put in the work.
You’d think the whole “I didn’t work out” thing would bother me, but nope! The loss of the streak is what bothers me!
Sure, I know I can “just start again,” but the whole point of this tirade is my admission that keeping the streak is somehow, inexplicitly, more motivating than the actual thing.
Why Streaks Are Powerful
I wanted to know why this works so well on me (and presumably others). Here’s what I learned:
Loss Aversion
It’s not just the steak I’d lose. It’s the effort, identity, and progress associated with it. And I (apparently) value a loss much more than a win, so I put in more effort to avoid all those losses.
Identity Reinforcement
Streaks become part of my self-perception. “I’m the kind of person who doesn’t miss a day of brushing.” Or “I’m the kind of person who values reading.” The steak acts as an easily identifiable external signal of the kind of person I am. This is why recovering alcoholics track how long it’s been since they had a drink.
The Zeigarnik Effect
Streaks keep a task “open” in my mind. If I don’t get to Duolingo first thing in the morning, I think about it the rest of the day, trying to remember to do it. [David Allen](https://en.wikipedia.org/wiki/David_Allen_(author)) would shed a tear for me. That desire for closure compels me to keep the steak alive.
Progress Triggers Dopamine
There’s actually a physical, addictive component to streaks. Each step releases dopamine, which reinforces my action. Knowing this kind of makes me want to do a streak detox and break all of them for a week. (But I probably won’t, hence the addictive part...)
Commitment & Consistency Bias
Streaks become a psychological contract with myself. I desire to be consistent with things I’ve already done, so a small streak starts creating internal pressure to remain consistent with my prior actions. The longer it goes, the stronger it gets.
So, streaks work because they intertwine behavior with emotion, identity, memory, and even brain chemistry. And thanks to smartphones and apps, streaks are easier than ever to create.
I’m unsure if my situation is a good or bad thing. I suppose since all of mine are healthy habits, it’s good?
But knowing how powerful they are on me, it’s good to be aware of for some not-so-healthy habit-forming apps, like some smartphone games.
PS. In case you haven’t noticed, I posted once a month last year. Here I am in the last week of March, keeping the streak alive...
PPS. This would probably work on me if it weren’t so hidden. Thankfully, Apple’s too concerned about my mental health to put it front and center.
All three are fantastic, with dozens of nuggets I want to remember (101, 97, and 104 nuggets, to be precise). I used to read a book, remember it for a little while, and then its lessons would fade into the background.
But no more.
Kindle
I bought a Kindle Paperwhite in 2013, and it felt magical. Being small and lightweight is nice, but the real perk is the built-in reading light. I love getting books instantly, but the built-in light is still the coolest part. While sleeping in an Indian hostel/camp while hiking in the Himalayas last year, a friend marveled that I could keep reading when it was time to turn off the single bulb in the sleeping quarters. It's such a simple feature, and I love it.
My biggest initial problem with the Kindle was that it didn't show book covers. After a while, all the books started blending together, and I couldn't remember where I read something or the author's name. It's incredible how passively looking at something 30-50 times for 1-2 seconds each time helps information stick.
Thankfully, Amazon eventually fixed my problem by incorporating book covers into the lock screen. (My last request for improvement is the ability to zoom in on graphics, as sometimes the rendering makes them too small to read.)
(side note: I also listen to audiobooks, but only books I don't want to take notes on or highlight. For me, those are biographies and fiction.)
Readwise
In June of 2022, I stumbled upon Readwise, and it's fantastic! The idea is simple: sync your highlights from an eReader, and it'll show you some highlights in a daily email (or the app). Or, manually add any book, and it'll show you popular highlights. You control email frequency and how many highlights are in each email.
The benefit is that it helps you remember what you've read.
Today, one of my 12 highlights was from a book I first read with my mom in 1998 and reread in 2019. Here's the crazy part: in 2019 - before I had Readwise - I highlighted 290 parts of the book!
At the time, I wrote a 4-page summary of the book because I wanted to remember its lessons. It was super helpful at the time, and I still have it saved on my computer, but the last time I opened it was in 2022 (I just looked).
But then today, I got a small reminder:
How cool is that? And it also sparks memories of related passages. Just like seeing a book cover for 1-2 seconds multiple times helps me remember the title and author, these snippets help me remember what I read years ago.
Since getting Readwise, I've used it a lot - 750 days in a row. It's the first or second app I open in the morning.
Physical Books
I like this system so much that I refuse to read paper books. When someone gives me a physical book - and I probably shouldn't admit this - I buy the Kindle version and then give away the physical book!
I figure the point of the gift isn't the book itself, but the knowledge shared by the author.
Though I'll admit, I'm starting to soften my digital-only stance. I'm currently running an experiment of keeping a bookshelf of physical books. My hypothesis is that seeing the books will act as one more memory enhancer and inspiration for other creative work.
My experiment is a little flawed because I read these physical books before buying my Kindle (I added them to Readwise and get popular highlights). So, it might be different to add a book I read digitally, but so far, I like having them in my physical space.
So that's what's working for me right now. If you use a Kindle, I recommend trying Readwise.
Celebrating 16 years of marriage... in the DMV parking lot waiting for an HP fireworks show. Eating a French picnic with some delicious local wine. You can't do crazy stuff every year. :)
Last year, I turned 40 and shared 40 lessons and quotes. I'm amping it up with 41 new lessons and quotes this year!
In a culture of increasing instant gratification, I find it hard to accept that I'm initially bad at something and need practice to improve. I'll try it three times, declare (to my inner self) that it's too hard, and stop.
No!
Making valuable things requires skills; frequently, developing those skills takes longer than I think. So, to help me get over the initial slog of learning, I commit to doing 100 reps of the thing before even thinking of stopping.
For example, when Jessi and I started our podcast, we committed to doing it for a year before looking critically at the stats. I figure the first 50 episodes are simply us finding our shared voice. Only after that can we start actually trying to improve and grow it, and then only after that can we assess if it's worth the effort.
Moments before starting our first episode
And guess what?! A few months in, we had a busy week, and recording a podcast felt like one too many things. And it wasn't even growing the business! But then we remembered that business growth isn't the goal this year. It's simply finding our voice and how it fits into our weekly rhythm. We took it as a learning opportunity and kept going.
Success!
Here's a free half-lesson: Translating internet numbers into real life keeps me grounded. When I post a video and "only" get 20 views, I remind myself that if I presented in a room to 20 people, I'd be excited. And when I hit 1,000 views, I imagine the venues required to host that many people—there aren't many in Corvallis. I'd be PUMPED if it were in person.
At the same time, I hold in tension the reality that BILLIONS of people could watch my stuff (and at least 100K ideal customers). So, if only 20 people see it, there's obviously room for improvement.
And that's the key. Within 100 reps of starting something, only focus on improvement. Don't even think about stopping. I'll even say it's better to focus on quantity over quality, and assuming you care about the output (not just doing it to check a box), improvement can't help but happen.
If you're learning something, do 100 reps without any thought of stopping. You got this.
Like most families, we have a lot going on: Jessi's job, my business, the kid's school, and everyone's additional activities. It takes effort to stay on the same page! At a minimum, ensuring someone picks up the kids each day can be challenging.
To help, we started holding what we call our "Meeting of Life."
It's a semi-formal meeting between Jessi and me to sync up on things happening in the next few weeks. We started simply by reviewing our calendars together, and it expanded into other shared areas of our lives.
Jessi and I have the meeting after putting the kids to bed on Sunday evening. It's typically 30 minutes, but some weeks, we only sync up on the critical things; other weeks, we spend the entire evening talking. It's been transformational, and I highly recommend it to everyone.
Here's what we do:
1. Pray
We start with prayer. We ask the Lord to guide our week and align us with His plan for the week.
2. Goals & Emotions
We then share our progress toward long-term goals and our emotional state. We talk a lot throughout the week, so there's rarely a surprise, but it's nice to know how each of us feels about our progress and life in general.
This part of the meeting can extend to an all-evening discussion. If it does, that's because it was needed, so it's all good.
3. Calendar
If we have limited time, this is the one we do. I pull up our calendars on my computer - a big screen where you can see the entire week helps. Yes, we have separate calendars for everyone because now the kids do their own activities. We double-check that drop-offs and pick-ups are covered and talk about irregular events - especially ones that impact the rest of the family.
We look at the next two weeks in detail, discussing each day. Then, we glance out a few weeks, looking for bigger upcoming events that might require planning.
Here's an example week. We have several recurring events, so sometimes there will be some overlaps with one-time events we'll need to resolve - and that's where we'll spend our time getting alignment. We're not crazy, right?
For the record, my normal view excludes everyone else's calendars, so it doesn't look this nuts (though, I do add my tasks, so it's a little nuts...). I cannot overstate how helpful it's been to get on the same page with our schedules! We still have double-booking issues or missing things, but they're much fewer.
4. Meal Plan
Once we have a sense of our schedules, we'll walk over to our meal calendar on the fridge. It's a dry-erase poster with five weeks on it. We re-write it once a month-ish, so it's helpful to ensure what we planned for food still makes sense for the upcoming week. We typically shop in two-week increments, so we also decide when to go shopping (and add it to the calendar).
On our meal plan calendar, we also note any big events that might impact the evening meal. So there's a bit of "two sources of truth," but it's super helpful to quickly see the context for any given meal.
And some weeks, we suddenly realize we're at the end of the calendar! Yeah, we're not perfect... We scrounge for a couple of meals (pasta!), or I'll make a quick trip (for pasta!) to get enough food to last us until we can update the calendar.
5. Finances
Now that Mint is dead, we use Quicken Simplifi to track our personal finances. So, once a month, I categorize transactions, and we look at our progress. I find the last six months over time for net income and expenses the most helpful views.
Here's the expense view. We start with this, and then I filter out big categories (like home, food, etc.), which updates the chart to break out more items from "Everything else."
Before we started regularly meeting, Jessi didn't pay much attention to what was going on. It was OK, but occasionally, it caused a problem because we weren't on the same page. Tracking finances is still a pain, but it's much better when we are aligned.
6. Chore List
We have an epic chore chart that needs resetting every week. Chores are daily, weekly, or monthly, so it's helpful to quickly see what's coming up. Sometimes, we look at something that's supposed to happen and decide to bump it because of what's happening that week.
And, I'll be honest: we're not perfect at this. Some days (weeks?!), we punt on it altogether. As long as we do it 80% of the time, it keeps our house in reasonable shape.
7. Homework and Dinner Discussions
We used to align on what the kids had for homework, but we simplified our weekly rhythm and don't need to discuss it during this time anymore. Instead, once in a while, Jessi will drop homework so I can see the kids' progress a pile of finis.
We also used to plan out some of our dinner discussions (especially on Saturdays - our quieter night), but we're working through a theology book with the kids, so we don't need to align on that, either. But, these were good for us to include so we could be intentional.
So, that's what we do. It's been invaluable to our marriage, and I recommend trying it out for the things in your shared life.
A lesson from business school that I'll never forget is simple: customers want your product or service to be free, perfect, and now. That's it. Simple.
And if I'm honest with myself, that's exactly what I want:
the lowest price/effort possible,
for the highest quality possible,
as soon as possible.
But here's the thing: I typically only get to pick two.
For example, let's say I want to buy my dream house. I will either save up a large down payment over many years, or get it now with a large loan payment. Or, if I'm willing to give up my dream house… dream, I can buy a different house now - in a cheaper location, in worse condition, or in a smaller size - to keep the payments low.
I run into this choice regularly with contractors. Usually, quality is fixed, which means I trade off on price and timing. My default is to be flexible on timing so I can get a better price, but sometimes, a property emergency forces me to pay top dollar to solve a problem immediately.
Keeping these trade-offs in mind helps me make smarter purchasing decisions.
The Business Side
I also find the business side of this framework fascinating. In general, your offering needs to be at least 2X better than their alternative in at least one of those dimensions to get customers to switch.
For example, I target a return for my investors that's 2X better than an alternative investment. And, I guarantee a minimum return that's inherently much better than the stock market.
That's the trick for seeing companies grow: can they offer a 2X or even a 10X improvement? And can they do it in more than one dimension?
Think about when Netflix started streaming movies and shows. They solved for "now," which was 100X better than going to a video store. By setting a fixed monthly price, they also got closer to free than anyone else. The trade-off, at first, was a small A-list catalog, but they solved that too by producing their own shows and buying more streaming rights. It's no wonder they're worth $270 billion!
When Amazon started, it focused on books. You could buy any book cheaply, but you had to wait for it to ship. And, famously, Amazon solved the shipping problem to the point that it's borderline more convenient to order something from Amazon than go to a store (which may or may not have what you want).
So, if you're starting a business, ask yourself how you can be at least 2X better on price, speed, or quality. If you can achieve that, you have the start of a compelling offer.
If you're considering investing in a business, try to understand how it's at least 2X better on one of those dimensions than their customer's best alternative (and how sustainable that advantage is). If you only invest in those businesses, your wealth will grow quickly.
I invest a lot in taking online courses. Some are a few hundred dollars, and some are a few thousand dollars! I love them because it's an opportunity to learn from an expert—with YEARS of experience—who took the time to analyze their craft, organize it in a digestible way, and then methodically teach it.
I know that I could search online for answers or learn through the school of hard knocks, but beyond the time investment, it's hard to separate the wheat from the chaff. I like having an expert tell me what's essential and in an order that builds on itself. Plus, most free resources don't go as deep—they don't provide the exact samples, scripts, models, etc.
Taking online courses is one of the highest ROIs I know.
But you can't just watch them like a TV show. After taking many courses, I've devised a method that works well for me. If I spend time and money on a course, I must get the most out of it.
I'll get to my exact steps, but first, let's talk about video games.
Mastering Video Games
Growing up, I mastered video games by following a specific method:
I'd play the game, experiment, and eventually figure out the controls. My brother and I were usually evenly matched, and often, he picked up skills faster than me.
Then I'd read the game manual cover to cover. Because I had the context of the game, the instructions would stick, and I'd learn the advanced skills of the game.
I'd leapfrog my brother. If it were a fighting or sports game, I'd demolish him.
Eventually, I'd teach him what I learned, he'd improve, and we'd become competitive again.
It's a bit of a ready-fire-aim strategy: try something (and flail), then learn how to do it properly, try again with much better results, and then teach someone else to cement the concepts. Then, keep practicing while re-reading the instructions to learn specific parts as needed.
So, when I'm considering an online course, it's because I've been trying something and feel like I'm flailing. Or it's because I have knowledge gaps that searching online doesn't fill, and I want an expert to fill those in for me.
Let's get into my process.
Step 0: Read The Book
Before I buy a course, I'll read the creator's work. If they have a book, I'll read it. If not, I'll download their "free tool/report" and subscribe to their emails. I want to sample their teaching style and expertise. Ideally, it's something paid that took effort to create (like a book) because they're not trying to sell me anymore; they're in teaching mode.
It has several benefits: 1) It's a cheap way to sample the course beyond their sales pitch. 2) I can try implementing what I learn to see how effective it is, setting me up for the lessons to sink in deeper. And 3) It often gives me a solid overview of the scope of the course.
If I don't have time (or interest) to read the book, tool, or report, I shouldn't take the course.
Step 1: Binge Watch Everything
I start a course with many questions and find it difficult to focus on the current lesson until I know my specific questions will be answered. So, my solution is to binge-watch everything. I don't take any notes or try to remember anything. Instead, I let the entire thing wash over me.
I aim to get the lay of the land and answer my burning questions. My experience is that there can sometimes be a lot of filler or things I already know, and binging helps me figure out where to dive deep in step 2.
But despite speed running through it, I still have TONS of ah-ha moments because I already have specific questions.
Step 2: Do The Exercises and Rewatch Lessons
Once I finish the course, I start over. But this time, I do the exercises and then rewatch the lessons on subjects I want to sink in. I'll also take notes and apply what I've learned. Doing the exercises before rewatching helps me identify gaps and know where to pay attention when I rewatch the lesson.
I usually find that I spend half as much time on this step as on the bring-watching. Part of the reason is that I don't rewatch everything (like intro videos)—I'm only diving deep into my knowledge gaps.
Doing the exercises is critical because I learn best when I try it. I even do those that seem trivial because A) I start with the assumption that the expert added it for a reason, and B) I often pick up a couple of knowledge bits from doing it.
For example, one exercise involved identifying good investment markets. I already knew how to do it, but forcing myself to do it revealed some areas for improvement.
Step 3: Refresher
I don't always do this, but sometimes I'll go back 6-12 months later and rewatch parts of a course. This is especially true for newer skills because I know there were nuggets of knowledge I wasn't ready to receive.
For example, when I learned to play bass guitar, I got proficient enough to play in my church's worship band but still had gaps. So, after playing for a few months, I rewatched some of the lessons and picked up skills I missed the first time.
Also, once a month, I'll pick one or two lessons from a course and rewatch them. I'll pick ones that feel relevant to whatever I'm working on. I'm not trying to learn anything specific - I'm simply trying to re-steep myself in the concept. And often, I have an "oh yeah… I remember that now" moment.
So that's my process. Online courses are one of the best investments you can make. For $200 - $2,000, you can learn from an expert in an organized, comprehensive course at your own pace. It's incredible.
I heard the line “safety third” on a podcast a few years ago, and I wholeheartedly embraced it. This might be a little pedantic, but I think it’s worth the distinction for my mindset.
Saying you believe in “safety first” is false. Nobody actually practices it. If a sea captain said they believed in safety first, they’d never leave the dock because that’s the safest thing to do - but if they did that, they wouldn’t be a real ship captain.
The first priority is achieving the goal.
To be clear, it’s not the only priority - it just comes first. If a goal didn’t exist, there would be no action and, therefore, no reason to declare any priorities.
And if you don’t achieve a goal for safety reasons, it feels like a tie. You’ll take it, but it wasn’t really the desired outcome.
Why Not Safety Second?
I prefer innovation as my second priority. How might I achieve the goal better? Is there a new innovative way to achieve it faster, cheaper, better, safer, etc.? It’s a priority of creativity and discernment that’s important to take before jumping into action.
This is how you get better.
What are the implications of a safety third mantra?
First, it promotes contextual awareness and assessing risk based on the situation. You don’t default to the least risky option. Instead, you evaluate your skills and the goal to make an informed decision.
Some questions that I ask to help me evaluate the risk include:
What are the worst things that could happen?
Could I get back here?
Is this favorable on a risk-adjusted basis?
Can I live with the worst-case scenario?
As someone who tends to be unreasonably optimistic, I sometimes have to enlist Jessi to help thoroughly evaluate the downside possibilities of doing something.
In this way, safety becomes more meaningful and not a meaningless platitude. Plus, if I know someone else has a safety third mindset, and they bring up a safety issue, I’m less dismissive.
Finally, you have to admit that some unwanted things will happen. But that’s OK! When they occur, focus on the good. What did you learn? What new opportunities does this create? There is ALWAYS something good that comes from bad things.
May you achieve your goals in an innovative way and be safe along your journey.
I'm sitting on my living room couch while Jessi finishes Marie Kondo-ing our shelves (I'm not allowed to help put things away), my kids are loudly doodling on random paper together, and my dog is quietly snoring while sound asleep beside me.
Life is good.
Though... it's not exactly the best writing environment, but that's OK. :)
The Lord has blessed our family so much that sharing everything He is doing is impossible. So, in this annual letter, I'll highlight my business progress, some personal things, and our travels.
Real Estate Syndications
I started the year pursuing a new-ish endeavor: syndicating multifamily real estate. I say "new-ish" because it's continuing what we've been doing for 14 years, but now people can passively invest alongside us. Pooling funds together for larger deals is a win-win business model: it allows us to grow and invest in larger properties (which often have better economics vs single-family rentals), and folks who may not have the time or expertise can contribute funds and enjoy real estate's benefits.
Pursuing syndications involves two primary activities:
Underwriting deals for syndication, and
Attracting new passive investors.
Oh yeah, and managing my existing portfolio.
A New 15-Bedroom Rental
In February, we bought a 15-bedroom co-living house. I wanted to syndicate it, but the financing didn't require it. Here's a video of it. It was also our first place to be managed by a property manager because hiring managers will allow our business to scale. We also transferred the storage facility to a property manager and plan to transition the rest of our portfolio in the next year or two.
I almost syndicated a property in Astoria, Oregon at the end of the year, but the deal fell through. I'll eventually do a whole write-up for my investors (join the club ), but here's the initial analysis video.
Going into 2024, I'll continue to underwrite deals and syndicate at least one. For intriguing deals, I'll create property analysis videos.
Attracting Investors
Speaking of videos, I started making them. My channel is small, but I've enjoyed sharing my knowledge and experience. My thinking is to make videos that people find educational (and entertaining) to build trust and credibility. Some of those people will choose to join my investor club email list, and some of those people will decide to invest in a future deal.
I'm new enough that I don't know my funnel ratios yet (It might be, for example, 10,000 views -> 10 email subscribers -> 1 investor). Research by Google in 2012 suggests that reliably building trust requires people engaging with me for 7 hours, across 11 touch points, in 4 locations (like YouTube, email, Instagram, webinars, podcasts, phone calls, etc.). So, I'm making it easier for people to spend 7 hours with me in many different places by creating content (I only have 26 videos that last 4.2 hours, so I have a ways to go).
Some of my most popular videos are property analyses, which is nice because they accomplish my two goals simultaneously: underwriting deals & attracting investors.
DJI Drone - My Favorite Purchase of 2023
Early in the year, I purchased a drone. I didn't have an exact use for it, but it seemed like 4-8 times every year, there would be a situation where having a drone would be great.
So, I bought one, and it's easily been my favorite purchase of the year.
Not only did I get pictures of each property, but I used it on multiple trips. What I like about it is that it lets me get otherwise-impossible photos. Though, I've noticed that videos are incredibly dull on their own. The videos work as b-roll, but when you're showing them to friends on your phone, it's boring. I also prefer looking at the photos on my big monitor because it lets me zoom in on all the little details. That is incredibly fun!
My primary use for videos has been for roof inspections. I can fly around to capture all the parts of the roof, and then view it on my large monitor at home while taking notes and annotated screenshots.
In Personal News...
I Turned 40
In some ways, it's just another candle on the cake, but in other ways, I feel older. For example, it takes longer to recover from a workout, and text is blurry first thing in the morning. But, along the way, the Lord has taught me a few things, so I wrote a post about 40 lessons and quotes I try to live by.
I Can Solve a Rubik's Cube
YouTube is fantastic for learning things. I found many videos showing the exact steps to solve a Rubik's cube. So, I learned it fairly quickly and practiced it for the rest of the year. My moment of heroism came while in India: we found a Rubik's cube on the side of the street in a random jungle village; I picked it up, solved it, and put it back. We went by that spot later, and it was gone. I like to think there's some kid whose mind was blown when they saw it.
This continues my quest to get semi-decent at mostly-useless skills to impress my kids, which also includes juggling and solving Sudoku puzzles. I think the next logical skill is to learn some card tricks.
My Favorite Books From Last Year
I don't think I'm an entrepreneur who thinks I'll succeed because I read a bunch of books. I believe that success comes from taking action and deliberate practice. Instead, my hobby, or favorite pastime, is reading. So, I read about topics I'm interested in: business, self-improvement, and faith. So last year, I read a bunch (here's my quick review of each one), and here are my favorites:
High-quality work is a function of time spent with distraction-free focus on the work. Newport gives strategies for setting up your schedule and work environment to allow for significant blocks of distraction-free time. The advice is actionable and reasonable. I've implemented his idea and enjoy my times of deep focus.
I love the "Bible For You" series because they go deeper than a sermon, but aren't as forensic as a commentary. The book of James is a sweet companion to the Sermon on the Mount. But James moves quickly, and it can feel scattered. Allberry explains how all the thoughts tie together and tackles passages that seem, on the surface, to contradict Paul's teaching. It's terrific.
This isn't a book on habits, ambition, or hard work. It's about unlocking... your potential. You do that by cultivating skills that maximize learning and setting up support systems to overcome roadblocks. The advice in the book is refreshing and highly actionable.
I was surprised by how different the book is from the movie. The book explores the differences between "machine logic" and "human logic" through a collection of short stories. In the book, robots act so similarly to humans that humans treat them as... human, which is OK 98% of the time.
But sometimes, robots do something seemingly illogical. And they call a robot psychologist to help determine the robot's logic. It's a bit of a mystery novel in that regard.
The movie, I think (?), takes place many years after the events in the book and explores what it looks like if robots are fully accepted by society (they aren't allowed on Earth in the book), but their machine logic is still slightly off, leading to... problems.
Honorable mention goes to:
Best In Class by Kyle Mitchell and Gary Lipsky - How to manage a property manager and the asset.
Show Your Work! by Justin Kleon - Ideas for sharing creative work publicly.
$100M Offers by Alex Hormozi - How to structure offers people want to buy.
A Christmas Carol by Charles Dickens - The original story, which is genuinely remarkable.
We Bought an Above-Ground Pool
The kids kept asking to go swimming, and after pricing a pool pass, we decided to get a small pool for our backyard. We wanted it big enough that they could swim around, but not so big that we feared them drowning. It was a huge success and the kids' favorite activity in the summer. Plus, it attracted a few kids in the neighborhood.
One of my favorite things was to run (as best I could in water) around the side and create a whirlpool for the kids to float in. And, the kids are much more confident in water, which is fantastic.
Lots of Travel
Real Estate Conference in Louisville, Kentucky
I started the year by attending a conference on raising capital for buying real estate. The speakers were great, and I made some excellent connections. I regularly referenced my notes throughout the year, so it was time and money well spent.
Sledding In The Snow
I saw a report that snow levels were crazy high at my grandmother's cabin, so we took an impromptu trip (~10-hour drive) to the snow. The snow was still taller than the kids, and they loved it. I also got to take some fantastic drone photos.
San Francisco For My Dad's 70th
My dad turned 70, and we celebrated in The City. It's always great seeing family. Plus, we drove over the Golden Gate Bridge!
India Motorcycle Trip
In July, Jessi and I celebrated our 15th wedding anniversary by riding motorcycles through the Himalayas in Northern India. It was a once-in-a-lifetime trip. I wrote about it and shared lots of photos here.
Yurt Camping (Without a Yurt)
In August, we went camping. I THOUGHT I had reserved a site with a yurt, but once we arrived, it became clear we didn't (we researched multiple campgrounds, and I got them mixed up). So... it was 8:30pm, and not only did we NOT have a tent, but we didn't have sleeping pads either. Here's a funny video of everyone's reaction the next morning.
West India Trip
In October, we headed back to India with some friends. We visited other friends who live there and hiked in the Himalayas. And we got to see Everest! The entire range is magnificent, and Everest blends in with the rest of them. So Everest isn't independently imposing, but it's still impressive. We also went through the jungles on which The Jungle Book is based and saw some fantastic jungle animals.
Looking to 2024
In many ways, 2024 seems like a natural continuation of 2023.
For example, my two business focuses are the same. I'll continue the same activities, though potentially doing more of them. And there's an 85% chance that Jessi and I start a real estate-focused podcast together.
We'll keep traveling, but we're not planning anything international. So far, we only have two plans: Elinor and I are going to a wedding in Louisiana and camping in California with my family. We want to visit Jessi's family, and I'd like to take the family on a backpacking trip, but they're not official plans yet.
Jessi will continue working at our church, and I'll continue serving at Love INC, the kids' school, and our church.
Part of the reason why 2024 feels like a continuation is that we both genuinely feel that we're living in God's will. It's not always easy, but it's good. So we'll keep on going! Thank you to all our friends for their support and the fun times in 2023.