School Advice from a Jealous Graduate

Six weeks ago I graduated. I recently wrote a letter to a friend (starting school this fall), with words of advice. I’ve generalized my advice here. I hope it’s helpful.

Tactical Advice:

1. Take classes that don’t make sense. I took every entrepreneurial / VC class I could, until they felt redundant. Then I took “Mortgages and Real Estate,” “Policy Time,” and “Global Business, Religion and Politics.”  It felt like taking off blinders. It put my interests in context and tickled my brain. Today I read about more subjects with more appreciation and curiosity. I wished I had branched out earlier.
   

2. Take classes you want. Getting into classes can be hard. But fight for them. Email professors (early) expressing interest. Show up on the first day. And the second day. And the third. People drop out all the time, and persistence is rewarded. Or be a TA (Teachers Assistant) for classes you cannot get into. 
   

3. Learn to write. By expressing complex ideas succinctly and clearly, I’ve earned jobs, relationships, and access to worlds otherwise out of reach. If you, like me, believe writing is magic - take writing classes. 

4. Make long term commitments. It’s hard to make standing commitments because you don’t know what you’ll want to do next month, or what other opportunities may become available. But do it. Commitments force you to spend time with people you wouldn’t otherwise spend time with. They allow you to accomplish things you otherwise couldn’t.
   

Personal and Interpersonal Advice:

1. Assume everyone has a secret. It’s tempting to categorize people: Finance Bro, Eco Warrior, Startup Gal, etc. You’ll think you have people pegged. You don’t. Everyone here has a secret or two. They’re hilarious, they’re going through something difficult, or they’re preparing for something amazing. You don’t need to go deep with everyone, but know that everyone has layers. If you peel them back, you’ll be rewarded.
   

2. You deserve to be here. You told your story in the application and it was appreciated. The best thing you can do now is be that person. Own the accomplishments that got you here, give in the same way you promised to, and attack the goals you laid out in your application. Be the boldest version of yourself. 
   

3. Be a driver. You’ll go on trips that aren’t your style, to parties that aren’t your vibe, and to restaurants you wouldn’t have picked. You can do things that are exactly your “vibe,” by planning them. School is amazing, in that everyone is looking for things to do.
   
   Give to others by organizing (poker night, bike ride, book club). It’s hard - but you’ll be rewarded with trips that are your style, parties that are your vibe, and group meals at your favorite restaurants. These events will attract people who share your preferences and are drawn to your qualities.
   

4. It goes really fast. At graduation from highschool, the four years I spent at Stevenson represented 22% of my life. At graduation from undergrad, the four years I spent at Middlebury represented 18% (4/22) of my life. At Stanford’s graduation, my two years at the GSB represented only 6% (2/31) of my life. The blink of an eye.
   
   So what does this mean? Don’t do everything. In fact don’t do anything automatically - think about how you want to spend each year, quarter, month, and morning.
   

5. Explore parallel universes. I found 25 people I love, 75  people I care about, and 200 people I know socially. There were another 200 I spoke to, but didn’t get to know. Occasionally a trip, meal, or class would throw me into the center of another social circle. Everyone was just as kind, just as smart, just as interesting, as the people in my circles.
   
   This is all to say: There are dozens of parallel universes. When someone gives you the opportunity to enter their world (dinner with a group you don’t know, a trip without your friends, etc), do it. And repay the favor. Invite others to your events, even if you don’t know them yet.
   

6. Take risks. At times I let my desire to “fit in,” keep me from saying something or trying something. I should have been myself more, because every time I took a risk I was rewarded for it.
   
   That's not to say that risks are without consequence. But the consequences of risk (embarrassment, pain, sadness, shame) vanished quickly. And ultimately each risk taught me something about myself or the world. I’ve heard others say this as well, so I won’t claim it as my own. But… I don’t regret a single risk I took. I regret not taking more risks.

While I could write you 10 more pieces of advice, I fear it would transition from helpful to self-indulgent. So I’ll stop. 

But I hope this helps. And I hope you have as much fun as I did. 

Jealously, 

Logan Randolph

Angel Investing Advice, from a Humbled Angel Investor

Tl;Dr:

1. Understand how contrarian your opinion is.

2. Be careful with “hot deals.”

3. Decide what you care about.

4. Do something. Anything.

5. Regulate your emotions.

6. Play to your Strengths.

___________

I wrote my first angel check in 2013, got lucky, and was hooked. 

I recently did my 60th deal, and increasingly I’m finding friends and classmates are asking for my advice on angel investing. Here are some lessons.

This probably isn’t useful if you are writing a single check to back a friend's first company.  But if you're thinking about making a habit of this, the following might be useful. 

Anyway, here goes.

1. Understand how contrarian your opinion is.

The first companies I funded were friends of friends, raising their first round. As I watched presentations, I took the founder’s claims and projections as gospel. These were surefire winners, and I was lucky to be “invited to invest.”

My ego told me I was special, because I was getting pitched – but I wasn’t. In Fact, these were slow rounds that other investors had passed on. 

By investing in slow rounds, I was taking very contrarian positions.I was missing red flags that others saw, and overvaluing an upside that others didn’t see. 

I’m not suggesting that you only invest in “hot rounds” alongside “big name VCs.” Some contrarian opinions end up being the right ones. And when they are, they pay off the biggest. But you must be aware when you have a contrarian opinion, and you must have some expertise that informs the opinion or thesis.

It also helps to ask yourself: why am I getting this allocation? If this is such an obviously great deal, then why aren’t people fighting for this investment?

At first, I would have answered: “This is an obviously great deal, and I’m getting access because I’m an angel investor, and I’m seeing this deal first.” This was super wrong. 

Today the answer is usually a little more nuanced: It might be: “I think that the risks associated with hardware can be mitigated for x reasons.” Or “This is an obviously good bet, and I’m getting an allocation because they want my help with recruiting.”  

It’s like someone is trying to sell you a plot of land in Texas because they’re nearly positive it has oil on it. It might. But there are people out there with geology PHDs on staff, who have equipment worth billions, who spend every waking hour looking for oil. To make the investment you have to articulate: what are you seeing, that they aren’t? 

2. The flip side of my first point: Be careful with “hot deals.”

By participating in a “hot deal”, in which there’s lots of interest from multiple big name investors, you’re taking a less contrarian opinion, so it can feel like a sure thing. But remember you’re still investing in the riskiest asset class. If you invested in every deal that a16z and Sequoia fought over, you’d probably end up with a great return. But you can’t, and you won’t. If you invest in one or two of the deals that a16z and Sequoia fight over… who knows what will happen. 

Don’t get seduced by sizzle – try the steak. Have a strong opinion.  

Furthermore, often deals look hot. But they aren't. Founders are getting great at creating artificially “hot deals.” Numerous times, this scene has played out.

Founder: We’re moving fast and closing next week. Can you get back to me Thursday? If not, we cannot accommodate you. 
Me: I like you a lot, but I can’t move that quickly. So unfortunately, this is going to be a pass. But I like what you’re doing, so I’d love to help with x, and stay in touch.
Founder: Oh… umm… when would you like to get back to me? I can maybe wait a little longer, and I really would like you in the round.

I don’t blame founders for creating urgency. I support them in generating momentum and being efficient fundraisers. But especially as a new angel making a limited number of bets, you need to think clearly (and not just follow the hype).

3. Decide what you care about.

Several years ago I became a fanatical early adopter of Whoop, so I reached out to the CEO. After getting to know him, I secured an allocation. This was empowering. It meant I could invest outside of my network. You can too.

It worked because Will could tell I care deeply about his product and industry. I’m obsessed. My partner rolls her eyes when new trackers, health books, sensors, and supplements, arrive at the house. I organically decided I care about healthcare.

More recently, I decided to go deeper into Enterprise SaaS and Fintech as well. This level of conviction and fluency isn’t necessary when fielding inbound deals, but it is essential when going outbound.

Focus also drives inbound as you can easily tell friends and investors what kind of deals you like (if you tell them you like everything, they’ll send you nothing).

4. Do something. Anything.

I invested in the Modern Treasury seed, but then wasn’t invited to participate in the A. This was a wakeup call. I had done the “how can I help” thing, and then not provided enough value.

Over the next six months, I helped Modern Treasury hire three employees. and with Whoop, I didn't want to take the chance so I referred a few candidates and helped them land a hard-to-get podcast guest. It worked, both companies let me participate in their next round.

So… If the founder asks for help, help. If the founder doesn’t ask for help, help anyway. For me,  browsing posted jobs, and trying to refer candidates is a straightforward and clear value add that doesn’t require work from the founders.

A friend of mine is an expert in corporate communications. For her, the value-add is to write press releases and blog posts for founders. Find something specific you can do.  

When you’re working with the best companies, money is a commodity and you’re selling them on why you’re a good team member.

5. Regulate your emotions.

When I first started investing my emotions looked like this:

Now it looks sorta like this.

Not perfect. But it’s better. 

I’ve come to realize that this hobby (and for me, it is just that) comes with highs. It’s intellectually fascinating. I get to know amazing founders. I can justify deep research into subjects I care about. I face new challenges daily (CRO search, vetting vendors, building GTM strategies), without the pressure that founders feel. I get validation from seeing my bets pay off.

There are also lows. There are days when doing this part time feels futile. I’m competing against some of the smartest people in the world, who have built huge organizations devoted to tracking founders, winning deals, and offering support. 

I rush into deals, and kick myself. I miss deals, and kick myself. I realize I’ve been too busy with work to help founders, and I kick myself.

I’ve found that I’m better at this (and happier) when I keep my emotions in check. It’s all OK. I’m doing my best. I’ve found it is rarely too late to help a founder (or company) I care about. Great deals aren’t usually as good as they seem. Sometimes underdogs win. And the economics are such that a few surprises make a big impact.

6. Know what you’re up against.
Thinking about who you’re competing with is helpful for many of the points above. When you’re frustrated: think about who you’re up against. When you think you have unique deal access, think about who you’re up against. When you think your contrarian opinion is right, think about who you’re up against.

I could expand on any of these points, but let’s look at dealflow. Here are the sources of my dealflow. 

At a tiny (fill time) firm, their deal flow sources might look like this. 

More often than not… I'm not the first person to see something! How could I be! 

And more often than not, I have less to offer. Be aware of this and play to your strengths. 

6. Play to Angel Strengths. Be flexible. Be small. Exceed low expectations.

Big firms have ownership and return targets and fund mandates, individuals usually don’t. Accept smaller allocations in great companies to get momentum. If you miss a seed or A, but really care about a company, chase the B.

Don’t compete with firms. Compete with most angels, who say “let me know how I can be helpful,” and then do nothing. 

Now what: I realize that many of these points are things to look out for, or things you can do wrong. I’m not trying to dissuade you from investing. I’m saying this: after a first call with a founder, when you’re excited to invest and proud of getting access… take a moment and pause. And consider some of the points above. 

If you’re still excited, good luck. Invest. And then turn your focus to earning your next allocation. 

FamTime, Be Real, and Healthy Social

In December of 2018…

I wrote the pitch below for a project I was calling “FamTime.” It was built around the idea that existing social media tools were not just failing to connect us… but were actually driving us apart.

I suggested:

• Time boxing interaction

• Limiting group sizes / connection

• Any dynamics that lead to more “real” connection.

Over the past few decades companies with this premise have come and gone. I’ve invested, tested, and even tried building (I put $100k and 6 months into building a FamTime prototype).

BeReal may be a flash in the pan (though I don’t think so). But more importantly, it signals an appetite for genuine connection, and healthy social media.

See my note below… many of the same trends, ideas, and observations, hold true today.

The Short FamTime Pitch 

(Copied from an email sent in Dec of 2018)

Differentiators

• 25 Friends

  • Benefit is you’re only sharing with people you care about. So you share more real things and you get closer to those people.

• Fixed Fam Time

  • Benefit is that you break an addictive habit (checking whenever you have 30 seconds free)

  • Benefit is you have a richer, synchronous experience with friends

V1:

Existing social media apps suck. We downloaded Instagram, Facebook and Snapchat to bring us closer together. Instead we’re following hundreds of people we hardly know. We spend hours each day scrolling through content from celebrities, middle school acquaintances, and advertisers. We’re addicted to these apps, despite the fact that usage is correlated with anti social behavior, depression and anxiety.

FamTime exists to actually bring you closer together with 25 friends, who are organized into “Fams” - one group might be your actual family, one might be your college friends, another might be your work friends. Like other social media applications, users share moments from their day via photo or video. Unlike existing platforms, users don’t consume these photos and videos whenever they want. They can only view content in specified consumption windows.

The result is that users spend less time in social media applications, and the time they do spend results in synchronous, real connection.

V2:

Here is how FamTime works. Throughout the day you capture moments from your day, and share them with groups of friends (called “Fams”). For most of the day, nobody can view the content that has been shared. Then at a specific time, everyone gets a notification inviting them to “FamTime.” Then, everyone jumps into the app, views the content, and has a conversation about what they’ve seen. It feels like sitting down at the dinner table with your family after a long day.

Today almost everyone has a group text with friends where they share photos and videos - FamTime is like this, but better. It really brings people together.

Enterprise Follows Social: The Rise of Short Form Video in the Workplace

TL;DR: 

• My Thesis… 

  • For decades, entrepreneurs have taken queues from the most dominant social technologies of their eras, to create enterprise native equivalents. 

  • In short: Enterprise Follows Social. 

    • AOL Instant Messenger => Gchat

    • Text / iMessage => Slack 

    • Skype =>  Zoom 

    • Facebook/Myspace => LinkedIn

    • Youtube => Loom 

• Why (does this happen)? 

  • We care deeply about social connection, so we experiment with social tools.  

  • Companies are bad at evaluating innovative ways to communicate. 

  • Social communication tools prove the value of new communication methods, and create social conventions around technology. Enterprises jump on the bandwagon. 

• So what? 

  • We haven’t seen the enterprise native equivalent of TikTok, Instagram, or Snap (short form / ephemeral video). 

  • These technologies / social conventions are well suited for solving new communication problems brought on by remote work. 

• Now what?  

  • I want to build, invest, and explore in this space. 

  • Slide into my DMs if you want to talk more about this.  

________________

Enterprise follows social: 

I believe there will be multiple billion dollar companies, who bring short form / ephemeral video to the workplace. 

I believe this because, over the past few decades, entrepreneurs have created decacorns by re-imagining social tools for the workplace. We communicated socially via asynchronous text (AIM) and synchronous video (Skype). We shared updates on Facebook, and complicated ideas with asynchronous videos (YouTube). These communication styles are now central to workplace communication (via Slack, Linkedin, Zoom, Loom). 

This is a predictable pattern that repeats for three reasons. 

1. We care deeply about social connection, so we experiment with social tools.

Our primary need is human connection. In Harlow’s famous study he offered baby monkeys a fake mother made of steel wire that dispensed food,  or a fake mother that’s soft, but doesn’t dispense food. They chose the mother that mimics comfort and connection over food. 

We (like those poor monkeys) value connection. The promise of personal connection is so strong that nascent ideas in this arena have a captive audience. 

Furthermore, the costs associated with experimentation for individuals is low. It’s free and fast to try and then jettison social apps. The same goes for entrepreneurs - they can experiment and pivot liberally, because their users are either addicted or disinterested (they’re not paying). 

My point: Social tools are like viruses. They will mutate and experiment until they find hosts (entrepreneurs), and paths to growth. 

2. Companies, on the other hand, suck at evaluating new ways to communicate: 

The communication needs of organizations aren’t as visceral. Costs, security concerns, internal politics, deployment issues, tool bloat… slow down tool adoption. This sucks for entrepreneurs too. They cannot pivot quickly, for fear of upsetting the delicate flowers that are their paying customers. 

The result: Corporate America isn’t the birthplace of novel communication ideas. Entrepreneurs intuitively know all of this, and are thus drawn to experiment elsewhere. 

So…. How do communication tools bridge this gap? 

3. Social tools prove the value of new communication methods, create social conventions, and teach new behavior.  

As an early employee at Quip, I found myself comparing Quip’s features to Facebook.

Facebook showed us the ease of using the “like” button to communicate approval. When we sold Quip, we said: “you can click ‘like’ to approve someone’s work!”. If we had to communicate the value of each feature from scratch, we wouldn’t have sold a single license. 

Social tools also build social conventions, and comfort (which drive adoption). 

The way we communicate in Slack, for example,  is deeply informed by the way we text. If you’ve learned to cook on YouTube, learning to do your job via Loom isn’t as scary. If you’ve coordinated dinner over text, coordinating a business trip over slack isn’t scary. If you’ve done a live chat with your family on skype, getting on zoom with your boss is more natural. You get it.

It’s still really, really hard. 

I’m not saying it’s easy or obvious who will win. Just because we used AIM / text, doesn’t mean Slack was an obvious slam dunk. But….the ubiquity of text communication (texting, AIM, Yahoo Messanger, MSN Messenger, WhatsApp, etc) was a great clue that a wave of corporate messengers would follow (HipChat, Slack, Teams, Google Chat, Chime, etc). 

Within this space (like elsewhere in enterprise software) bottom up software has the best chance of beating the odds. 

In our social lives, the best communication tools spread virally without a central decision maker or IT department. When the best communication tools jump to enterprise, they grow in the same way. The closer an enterprise company is to its social counterpart, the more comfortable people will be sharing it, adopting it, and supporting bottom up growth. 

This trend leads me to believe that short form video and short form ephemeral video will soon be used to communicate in the workplace. 

At first glance, TikTok, Instagram, and Snap are simple, one-way, broadcast tools. They’re useful for sharing where you are, what you’re doing, or content that your followers should see. 

But the value comes from the interaction. We tag friends, and share content via DMs. We seek advice via forms and polls. We relish in likes and comments. This interaction connects us to friends and family around the world. It educates and entertains us. 

Connection, Context, Education, Entertainment… these are powerful results that certainly could be of use to companies.

Here are three problems this technology may solve in the workplace. 

Communicating emotional information, in a remote first environment, is difficult. 

Communicating via text (slack, email, text, etc) is great for communicating tactical information, but awful for communicating emotional information, like values, culture, or mission. 

Video meetings (synchronous or asynchronous) can be great for communicating emotional information. But they’re infrequent. You might have one all hands a week, one team sync a day, one meeting with your manager per day, etc.  

When large meetings are virtual, leaders still struggle to read the room, and engage the audience. 

This is creating problems with unmotivated workers, high employee churn, and misalignment. Every day we see examples of CEOs taking grand steps to realign companies, which are fracturing (like Brian Armstrong at Coinbase). 

Reading and writing is taxing. 

Even though reading is faster than watching videos, it’s more taxing. It requires mental and ocular focus. 

Writing is also tiring and slow. Before the pandemic, I often stood up in the middle of a Slack conversation, walked to my coworkers desk, and said “Let me explain in person.” 

I know this behavior could be mimicked with a Slack Standup, A Zoom Call, or a Loom. But ephemeral video would better mimic the lightness of stopping by someone’s desk more closely.  

It’s hard to make work friends. 

This might seem unimportant, but it turns out having a best friend at work is pretty important. A gallup poll (2018) found that if you have a best friend at work you’re twice as likely to be engaged, you produce higher quality work and you’re better at engaging customers. 

Short form video could certainly help here. Videos are great at expressing personality, entertaining others, and creating connection. Ephemeral videos are lower stakes, allowing us to be silly, sad, vulnerable, or excited without concern. 

Specific Solutions: 

I described some really vague problems. But I think the solutions will be really prescriptive and specific.

Video tools will not be for “communicating emotional information,” they’ll be used for “top down communication from execs” or “daily updates from traveling salespeople.”

Objections.

• Loom already does this. Kinda. Maybe. It’s desktop based. It’s content focused (default is focusing on your screen, not you). It’s designed for building a database of videos, rather than facilitating light, disposable / ephemeral content.  Loom to me feels closer to YouTube, than Tiktok, Snap, and Instagram.

• Mobile doesn’t matter, Most people are in front of their desk. To me using mobile video isn’t about communicating on the go. It’s about communicating quickly, from a secondary device we’re already comfortable recording video with.

• Tool fatigue. We’re already juggling 12 communication tools. This is a fair point, but it’s part of progress. New tools come in, and old ones fade. In our personal lives, old tools fade quickly (nobody has a fax machine, or even landline). At work, it does take time (offices still have landlines, fax machines, etc). 

So what…

This is the future that I see. 

I’ve conversed with 30 executives in an effort to understand the problems they’re facing, and how short form / ephemeral video may help them. At a later date I’ll dive deeper into their stories. 

There is something here. 

I hope you’ll reach out if you believe short form / ephemeral video is the future, or working on something in the space. I’d love to chat, invest, or collaborate.

Going for a Picnic

On July 27th 2021, I completed “The Picnic,” an unofficial mountain triathlon on the Grand Teton.

The Picnic is an endurance event with the following distances:

⁃                Bike from Jackson to Jenny Lake: ~23 miles

⁃                Swim across Jenny Lake: ~1.3 miles

⁃                Run / Rock Climb to the summit of The Grand Teton: ~10 miles, ~7k of vertical

⁃                Have a picnic on the summit

⁃                Run / Hike / Climb back to the lake: another ~10 miles, descend ~7k of vertical

⁃                Swim back across Jenny Lake: ~1.3 miles

⁃                Bike back to town: ~23 miles

After training for around 6 months, I completed the event in 18 hours.

Even though training was a big part of my life, I didn’t tell many people about the goal. I didn’t want my friends forcing me to recount a failure, if things went sideways on the mountain (or in training). I also think it’s cool when people do rad things nonchalantly.

Note: I realize that posting a trip report (like this one) makes it very not-nonchalant.

I could have picked any day for my attempt because the Picnic is unofficial. There’s no sign up, or website with FAQs. Years ago, a Jackson Hole local thought “wouldn’t this be an epic challenge.” He biked to Jenny Lake, swam across, climbed the Grand Teton, then did it all in reverse, and called it “The Picnic.” He has since done other “picnics” with other natural objectives.

I picked July 27th because it was nearly a full moon, the days were long, and Jackson weather in July is generally stable. I also wanted to enjoy the month of August without training pressure.

I have no idea how many people do The Picnic. Maybe dozens each summer? If you’re an outdoorsy person in Jackson, you know people who have done it. If not, it’s rare to hear about it. On July 27th, 2021, I was the only one to attempt the challenge.

Bike 1 - 12:50am

My bike wheels started turning at 1 am as I rode under the antler arch in Jackson’s main square. When I hit the edge of town, the temperature dropped 5 or 10 degrees - enough that I contemplated turning around to get the jacket I’d left behind. Ten minutes later, I was comfortable. It wasn’t an especially cold night, except when I rode through pockets of cold air that settled in the lower points of the valley.

Only two cars (containing Carter and CJ – my support team) passed me as I biked the 23 miles to the Jenny Lake Overlook. They stopped three or four times to cheer me on. I’d see their lights a mile ahead, then I’d hear music, and finally I’d see their silhouettes as they yelled words of encouragement. The interactions were short (I didn’t slow down), but much appreciated. They danced in the headlights, played music, yelled. And I yelled back.

For the most part, the ride was dark and quiet. As I entered the park, I saw elk to my left and right. At one point, a huge buck barreled across the path 30 feet in front of me. The sounds of cranking branches, stirring brush, and hooves on pavement pierced the otherwise silent evening. For a moment, I was terrified.

Swim 1 - 2:42AM

At the Jenny Lake Overlook, I threw on a wetsuit and scrambled into the water, where Carter and CJ were waiting for me on paddle boards.

I expected to cringe as I waded in, but the water was warm - I threw Carter my thermal swimming cap 15 minutes in. For most of the 45-minute (1.3 mile) swim, I couldn’t see anything. The water was black, and so was the sky. Smoke from distant fires hovered in the air, counteracting the effects of a full moon. I paused a few times in the middle of the lake to take it in. The still lake, the glow of the moon through the smoke, my friends paddling alongside me, and the silence (only interrupted by the sound of my breathing and soft lapping water).

Fighting against my wetsuit was a new sensation. But the floatiness felt fantastic.

When I reached the boat dock on the far side of Jenny Lake, I pulled myself out of the water and focused on my body. How did I feel? I hoped the bike and swim would be a “warmup,” and they were. I changed quickly, splayed out my gear for one final check. And then started to eat. The remainder of the day would be low intensity work (so I thought), so I figured bringing on as much fuel as possible would give me the best chance of success.

At 4 am, I hugged Carter and Christian goodbye, and hugged Gavin hello (a friend who met me on the far shore and planned to climb with me). The four of us took a photo together and I was overwhelmed with gratitude. Here, on the far side of a lake, at 4 am, this dream team gave up sleep, and assembled… for me.  

I’m lucky to have such great friends.

The Climb (and descent) - 4:00Am to 4:45Pm

The first few hours flew by. Gavin and I chatted easily and frequently about gear, climbing, mutual friends, mountain stories, his backpack company, the route, the plan, and more. We hustled, walking quickly uphill, and jogging downhill and along flats. We stopped a few times for water and food, and everything was going well.

Moving in the dark was nice. There was no sense of the distance we’d traveled, or the relative grade of the hill. We just moved. Up the switchbacks, though the meadow, and beyond.

As we approached the lower saddle, my body reminded me this wasn’t a normal hike. I was getting worn down. It seemed to be a combination of the early morning (I hadn’t slept the night before), the elevation, and the exercise I’d already done that morning. Usually, I’m able to take on food and drink, and recover like magic. But here, no matter what I did, I felt like garbage.

Dehydration may have contributed to the situation. I had opted to travel lighter (with less water) and fill up at springs along the way. But in hindsight, I should have carried more, without the distraction of considering water stops or rationing.

We stopped at the lower saddle, refilled water bottles, and continued. From there, we scrambled to the upper saddle. This section required one or two “climbing moves” but was mostly navigating crumbling rock and small boulder fields. It reminded me of the Disappointment Cleaver on Rainier (a scramble section of the route, that I’ve done 100 times).

Despite my comfort moving through the terrain, I still felt like shit. Gavin was kind enough to slow down, pretending to search for the best path through the rubble – but I knew he was just letting me catch my breath.

Even though we were slowing down, we still made great time. We reached the upper saddle and discussed whether we should solo the upper section (more technical and exposed) or use ropes. We opted to solo (climb without ropes). We put on harnesses just in case but didn’t end up using them.

The first couple sections were the most technical. But they were also a joy. A few short sections required 5.4 climbing moves, with 3,000 feet of exposure below my feet.

I told my mom it’s like climbing a latter on the side of a skyscraper. It’s not hard at all. Most people could do it comfortably on the ground. But… you do have to focus when the consequences are real.

After the two most exposed sections, we moved onto the chimney, another straightforward 5.4 climbing pitch with 30 to 50 feet of exposure. We lucked out on the timing – even though the Owen Spalding route is often crowded, we never got caught waiting for folks in front of us.

The final push to the summit was the best part of my day. I forgot the pain I was feeling in my body and got into the zone. I focused on the route and the view, and enjoyed myself. And then… we came to the summit and high fived. We took it in for a moment, took some pictures and turned around.

We hustled down to the repel site and took a proper rest waiting for the repel anchor (15 minutes).

We could have down climbed. But this is probably the most dangerous part of climbing, and I didn’t feel the need to challenge myself here. Gavin had also carried a rope all the way to the summit, so I figured we might as well use it.

We repelled and then moved quickly down the upper saddle.

From the lower saddle to the trailhead, we moved efficiently but not quickly. I felt great. Truly. Nothing hurt (except a blister), I had tons of energy, and I was feeling composed.

At the trailhead, I left Gavin and started to run. I thought the boat dock (where I’d enter the water again for my swim) was a mile away, so I set an aggressive running pace. The reality: the boat dock was over three miles away.

As I ran down the dusty road, backpack bouncing, I periodically slowed to check my progress on my phone’s map. I was a bit disappointed at how slowly I was moving.

I sped up my pace, threw back a few snacks, and got frustrated. “I should be there by now,” I thought, “am I on the right trail?”

I started to bonk. I had been pushing an aggressive pace. I had taken one too many shot blocks and consumed too little water. Sunscreen ran down my face, and my mouth dried.

An hour before I was thinking “this is too easy, why am I not suffering.” Well… here it was. I was suffering.  You can actually see my heart rate skyrocket below.

Heart Rate, Distance, and Elivation

I got to the boat dock and met Carter (who had paddled across to meet me) and laid on the ground, on my back. I was moody, nauseous, and wanted water. I started to worry. I knew I’d finish, but I wasn’t sure if the coming hours would be enjoyable at all.

Swim 2 - 4:45pm

I drank some of the water Carter brought with her. I put on my wetsuit. And soaked in the lake. My core temperature dropped, and I felt better. As I floated in the lake, my nausea subsided, and my mood improved.

I took a deep breath, gathered myself, and pushed off the shore for my final swim. Side cramps periodically halted my progress, forcing me to tread water and stare at the far shore. At 2 am, I complained about not being able to see the other side. In the afternoon, seeing the other side sucked – it didn’t seem to be getting any closer.

About 15 minutes into my swim, the calm lake started to stir. I found myself bobbing in a growing swell, which I assumed was from a passing boat. It wasn’t. The wind had kicked up, generating a consistent chop, complete with white caps. At least it was going the right direction.

As I got closer to the shore, I paused a few times to take it in. On the far side of the lake, I saw shimmering cars in the parking lot. Behind me, a tremendous peak, and around me clear, cold water. I wasn’t just observing this landscape, I was emerged in it. Swell lapped my neck and lifted me up and down, the distinctive taste of lake water covered my lips, and the wind cooled my face.

Carter (on a paddleboard) had hung a blue backpack on the shore, so we knew exactly where we were going. I looked down into the blue nothingness. Then… the bottom started to come into focus. I saw a huge tree, rotting, on the bottom of the lake. Minutes later, I saw the beautiful mosaic of round, slimy, stones at the bottom of the lake. Like marbles. Green slime balls. They almost looked like food. And it meant that it was getting shallower. They got closer and closer until I stood up.

I had a ride ahead of me. But I’d done the hard part.

We got out of the water and, with some difficulty, and addressed with the hardest part of the day: Getting the paddle board up the steep, dusty, goat path up to the parking lot.

“Did you swim all the way across the lake?!” people were asking in disbelief.

“Yep.”

Bike 2 - 5:50pm

Carter had a sandwich and coke for me in the car, but they’d both been sitting for a few hours (the descent took longer than anticipated) so I just sipped the Pepsi. I wouldn’t have eaten anyway, at this point I felt like I was going to throw up again.

I changed into my cycling gear and left a pile of soggy gear on the ground. I did this several times this trip (leave stinky clothing in a transition zone). Carter was a hero, taking care of so many big and little things (like this) throughout the day.

I wanted to rest and let my body calm down so I could eat. But I also wanted to get the ride over with. So, I jumped on the bike, planning on sipping and nibbling along the way.

As I rolled out of the park, I couldn’t help but smile. Some moments felt magical. I passed a field of horses grazing on long grass, sprinklers on and the evening light illuminated the mist. This stood against a background of the Tetons. I stopped to take a photo.

At other times, I had to grit my teeth. The bike was too big (rental company didn’t have the bike I reserved, despite booking 2 months earlier), and I was starting to feel this. My body didn’t feel good. As I sipped electrolytes (1/3 of a bottle over an hour) my stomach turned.

Twice, I almost crashed my bike. First, I was looking at my watch checking my speed (which I did periodically) and the bike path turned. I was fixated on my watch, so I missed the turn and went flying off the bike path into low brush. Luckily, I stayed on the bike, came to a stop, and got back on the path.

The second time, I saw two teenagers on the path. Both were stopped right in the middle of the path. I yelled, they looked up, and then mounted their bikes. They rode to different sides of the path, leaving me a path down the middle. But at the last minute, the one on the right decided to switch side and join his friend.

I had to slam on the breaks, but I only used the back break (maybe my other hand wasn’t on the break) which sent me into an 8-foot back wheel skid. I corrected and rode out of it, aware that now that I’d been a part of two near misses, this was probably on me. I was getting tired. I needed to focus.

My breathing became labored. I wasn’t sure if this was the result of hours of physical exercise, or if I was reacting to the smokey air (forest fires outside of Utah changed the AQI to 75 that day).

The last 5 miles you can see Jackson, which is awesome and torturous. I wanted to be there. I put my head down and pushed.  

I reached the edge of town. Navigated the crowded streets. Stopped for several crosswalks. Then reached the town square.

I pulled over and walked through the antler arch. I stopped my watch. And lay on the ground. Carter brought me drinks which I sipped.  

I couldn’t believe I had done it. I had assumed something would derail me. But the stars (conditions, my training, my support team, my health) had aligned.

We walked to a touristy burger joint where I downed a burger and fries. In front of me was a beer, a root beer, a Gatorade, a water, and a recovery shake. I downed them all, went home, showered, and fell asleep without brushing my teeth.

Not a bad day.

Thank you

Thank you to Carter for tolerating my training and traveling with me to Jackson. For renting a paddle board, buying food, and running other errands as I prepped my gear the day before our ascent. For staying up all night, paddling across a dark lake, and coming back on a paddle board to get me. For dealing with piles of stinky clothing, and a stinky man. I love you.  

Gavin and Christian, many studies have shown how unhealthy it is to stay up all night. Scientists have found that sleep deprivation takes years off your life; makes you look less attractive, and negatively effects mood. Thank you for doing it anyway. For carrying gear, supporting me with kind words, and sharing my excitement.

To the three of you. My picnic is a highlight of all my years on planet globe. Thanks for sharing the day with me. I’ll remember this kindness forever. I say this with no hyperbole: I couldn’t have done it without you. Thank you.

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