I was thinking about this concept — money is like water — after attending a PEF event meant for founders who are post-exit and looking for their next venture.

A common theme amongst founders in the group was a desire to work on something with clear market pull. The kind of product-market fit that Mark Andreessen or Mike Maples Jr. would describe — where customers are requesting new features faster than you can build them and pulling product out of the team.

The meditation brought up a childhood memory I hadn’t thought about in years.

When I was in middle school, my dad took me fly fishing on the Penobscot River in Maine. Each day of the trip centered on a different fishing spot where Landlocked Salmon were supposedly abundant. On this particular day, we went to “the dam.”

My dad had an old boat, one he bought cheap and fixed up. Before the trip — an eight-hour drive — he tested the motor in a large bucket filled with water behind the house. It was running fine. But on that day, the motor wasn’t a match for the Penobscot’s current. Our boat got stuck and we couldn’t get upstream to the dam. We couldn’t tell if the boat’s motor was malfunctioning or if the river was just too strong.

I remember watching the other boats pass us embarrassed. I kept thinking: if we had more money, we’d have a better boat and we wouldn’t be stuck here. In retrospect, this was a rather entitled thought. That’s a different blog post.

We tried maybe ten times. Every time we’d make it up the river, the current would just pull us back down while the other boats watched. My dad was visibly pissed off. He never really swore, so he just kind of mumbled under his breath and made angry faces. Maybe he should have just said “fuck!” and released some tension. That’s also a different post.

This particular spot, on the river by the dam, was *where* to catch Landlocked Salmon. If you fish enough and you’re on the scene, you know where the spots are. My dad’s friends were all upstream already. We thought about packing it up and going back to camp.

After some discourse, we decided to drive downstream instead — a path the boat could actually handle. The river opened into a lake and we started trolling.

In case you’re unfamiliar with trolling, it’s a type of fishing where you cast your line off the back of the boat and just cruise. I never really liked fishing, and still don’t, so this lazy yet effective method worked fine for me. My dad probably chose it because mustering up energy for any other fly fishing technique was too much after the motor fiasco.

Like most childhood stories, the likelihood of revisionist history here is high. But this is exactly how I remember it. And as far as memories go, I’d say this is a core one.

About an hour into trolling, my dad was chilled out. We began chatting.

I don’t remember exactly what we were talking about, but I do remember it was one of my favorite dad chats. The lake was insanely beautiful. It felt like I was on the Discovery Channel and my dad was the narrator. This man loved nature, and I mean loved — daily morning walks in the woods, hunting trips that returned no game but a camera roll of photos, bird books, Cabela’s catalogs… he even planted some special kind of clover behind our house so deer would graze in our yard. (They did.) We talked about nature, and that day I “got it.”

Here’s one of the many photos my dad took fishing in Maine.

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Just as we were settling into nature, a bald eagle swooped down right in front of us, grabbed a salmon out of the water, and flew off. Some National Geographic shit.

As it happened, we looked at each other elated. There was like this spark of mutual understanding — like wow, glad we were here for that…

…And I kid you not, within moments of a bald eagle flying away with a fish in its talons, a loud “clunk” sounded from the boat’s rear. As if something stuck in the engine had now released, the boat kicked into high gear, speeding up 2x and surging forward.

What followed was laughter that’s hard to describe: true joy mixed with a kind-of mad scientist hysteria. Like… What just happened? How? The moment had a grounding effect of shared gratitude and connection. Plus, let’s face it, my dad was proud he wasn’t crazy about the motor. So there was a little “I told you so” thrown in there too.

So what’s my point? How does this relate to startups? What does this story have to do with a PEF event and my random morning meditation in Miami?

Trying and willing the boat upstream didn’t work. Our motor wasn’t strong enough, and there wasn’t much we could do differently in that moment. What did work was going downstream, where the river was already flowing and where our boat could easily travel.

The moment we stopped fighting the current and complaining about the boat, the boat worked. Plus, a fucking bald eagle — the only one I’ve ever seen IRL — literally showed us where the fish were. We had an entire pool of fish, all to ourselves, downstream.

It’s my educated observation, after working with hundreds of founders and being one, that many of you are building businesses trying to force an outcome. It’s usually based on some preconceived notion you have on how things are supposed to go.

When something doesn’t work, it doesn’t work. And it’s usually really clear that it’s not working. The problem is we fail to read the signals because we’re too tunnel-visioned on the outcome we want. We should be observing the reality of what’s happening instead.

In a river of horrible advice on this matter, pun totally intended, Sam Altman’s take is great. Burnout isn’t caused by working too much. It’s caused by working on things that aren’t working — like trying to get up-river with an old motor that can’t hang.

What I’d offer is this: stop focusing so much on how you want things to turnout. Or how you wish your customer would use your product. Instead, focus on what’s clearly, bright-as-day working. Observe reality for what it is.

Let’s call the things that clearly work rivers. Rivers in startups look like:

• Markets that are obviously picking up speed

• Technology inflections that make certain things possible that weren’t possible before

• Features your customers tell you they want but you ignore*

*When you’re listening to customers through the lens of wanting things to look or go a certain way, it’s easy to miss what they actually say.

And then there are the boats. Boats in startups are:

• Industries, products, or problems you uniquely understand based on your experience

• Skills and tasks you’re actually good at and that give you energy

• The team you can naturally build based on your existing network*

*I once asked an early Airbnb employee how they chose to design CX. Paraphrased, he said: “We hired our friend who knew CX. That’s how CX at Airbnb was designed.”

Boats are like what Warren Buffet famously calls your “circle of competence.” They are your unique competitive advantage, and they allow you to travel places that others aren’t seeking out — like a pool of fresh fish that others aren’t paying attention to.

Use the boat you’ve got. Follow the existing current.

That day on the Penobscot, we thought the goal was getting upstream. The spot by the dam where everyone else was fishing. We were actively frustrated when it didn’t work out.

But the current had other plans. By following it, we ended up in a place where no one else was fishing which worked particularly well for our boat. We caught plenty of fish in the lake using a method that took little to no effort. And the oddest part was that by doing so, our motor started working and we were able to cruise upstream.

I think I finally get this “money is like water” thing.

That same September, I gave notice that I was leaving my job in equity research. I loved the work, but it was time to move on. I also turned 30 that week. The book felt like it was published at the exact moment I needed a push to make a change — one I’d been mulling over for most of that year as my birthday approached.

There’s much I loved about the book, and I was reminded of its primary lessons this weekend after re-stumbling upon this video from #2016. I’ll revisit some of the book’s core themes below. But there was one thing in particular that struck me more than anything, and at the time, reinforced my choice to design an entrepreneurial career path.

From Chapter 10, “The Mechanics of Mafia”

In the most dysfunctional organizations, signaling that work is being done becomes a better strategy for career advancement than actually doing work (if this describes your company, you should quit now).

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At the time, I was vying for a pay raise — one I could only get by receiving a competing offer from a rival bank. (My direct boss actually encouraged me to interview, pointing out others at the firm who’d secured higher pay this way.) I took his advice, interviewed around, and landed a verbal offer from a competitive firm that paid double.

But then, literally that same week, I read chapter ten. A few weeks later, I quit and took a job at a startup I was advising on the side — one that paid half instead. The text resonated. I wanted upside tied to my output, not my ability to interview and “play the game.”

I’m more comfortable with competitive dynamics now than I was back then. At the time, I was frustrated that being a top performer wasn’t enough. I was more incentivized to interview around than commit to the organization and stay focused? That frustration absolutely contributed to my decision to quit. But I’ve come to realize that if you want to work on Wall Street, or in any competitive field, you do have to stay sharp and play the game. I’m not suggesting you leave the game altogether. (Take it from someone who tried. It doesn’t work.) What I am suggesting is to choose work where the game isn’t the thing. You can choose work that’s generative and creative. Where the incentive to create value for other humans and produce great work outweighs one’s ability to interview well.

Peter Thiel: Going from Zero to One (Video from 2016)

Starting or joining an early-stage company is one great way to produce great work and create value for other humans. So is funneling capital toward these endeavors, in my opinion. Everything a startup creates is net new, even if it’s a riff on an old idea.

So in the spirit of things that are ten years old, and older, here are a few lessons I learned about building and investing in new things from watching this video on repeat in 2016:

• Competition is for losers. All unhappy companies are the same because they endlessly compete with one another. All happy companies are different because they’ve escaped competition. I think this applies to people, too. Society has a tendency to discourage original, creative thinking in favor of conformity. Most of us have experienced that ick feeling of comparing ourselves to others. Competing with others directly is more of the same. You can win your market, and your life, by escaping competition and doing something creative, new, and true to your unique viewpoint. Sure, you’ll have to play the competitive game sometimes. If it weren’t for competitive markets, we wouldn’t get to create new things at all. But your ventures, projects, and career choices can be more about your self-expression than the game.

• Go for monopoly. Contrary to conventional wisdom, successful capitalists—investors and founders—don’t seek competition. They aim for monopoly. And opposite to popular opinion, attempting to create a monopoly is good for the world. When markets are perfectly competitive, economic theory teaches us that all profits erode to zero. This has generally played out true. Zero profit means nothing left to reinvest, which means fewer jobs, fewer new products, and less return on invested capital for investors. The entire pie shrinks, and worse, usually leads to increased borrowing and bad behavior. We know how this story goes. Monopolies get a bad rap because of US antitrust laws, so companies like Google, which monopolized search, pretend they don’t have one. Meanwhile, small startups pretend they dominate markets when they don’t.

• Secrets exist. There are undiscovered truths about the world that one can find through persistent hard work and independent thinking. Thiel distinguishes between “conventions” (things everyone knows), “secrets” (things that are hard but possible to figure out), and “mysteries” (things that are unknowable). Fields like basic chemistry appear fully explored, but areas like biotech, space exploration, and AI still hold massive untapped potential. Secrets don’t always need to be earth-shattering. PayPal’s secret was that you could combine email with money and make it easier for people to transact on the Internet—difficult to achieve but not impossible. Thiel argues that the most valuable companies are built on secrets, and that the best way to uncover secrets yourself is to ask: what do I believe to be true that most people think is false?

• Technology is zero to one. Going from 0 to 1—creating something new—is fundamentally different from going from 1 to n, which is copying what works. Globalization is a 1 to n activity that leads to horizontal growth: taking things that work and spreading them everywhere through copying. China persistently copying what works in the West is the best example of globalization, and there’s nothing wrong with it. Technology, on the other hand, is a 0 to 1 activity that leads to genuinely new things. The contemporary view has a tendency to treat the developed world as a place where nothing new will happen. But Thiel and Silicon Valley in general ask the contrarian question: how might we continue to develop the developed world?

Siri, a startup Apple bought for roughly $200M, first launched on the iPhone in 2011.

Today, that price might look like a steal for a major incumbent buying an AI company. But the Siri experience, under Apple’s roof, has remained fundamentally unchanged for nearly 15 years. Now the iPhone’s architect Jony Ive works for OpenAI. And if you ask Siri a complex question, it’ll ask if you’d like to use ChatGPT to get the answer.

I’ve been surprised there hasn’t been more news on what’s coming this year in hardware land. OpenAI announced it acquired Jony Ive’s “io Products” for ~$6.5B in stock six months ago. Since then, ChatGPT added another ~100M users by most estimates, bringing its total user base to just under a billion. For context, Apple’s total installed base of iPhones is roughly 1.5B, which represents about one in every five people on the planet. This compares to one in every nine or ten humans using ChatGPT.

Comparing the number of ChatGPT users with Apple’s iPhone installed base is somewhat of a fool’s errand. Apples and oranges, one might say. Especially since only ~5% of OpenAI’s users are paying customers and ChatGPT is software and not hardware.

Still, a consumer application achieving 1B users in three years is wild. How wild, you ask? Instagram took eight years to reach 1B. TikTok took five years.

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From Innovation to Artifact

Devices like Google Home and Apple HomePod already felt dated to me, even before ChatGPT. Now they feel like relics from another era.

For example, my favorite restaurant in Miami is Sunny’s. I go often, and each time I use Apple CarPlay to navigate there. On the first attempt, Siri always finds some other place called “Sonny’s” which is six hours away — impractical to say the least. (And separately, Sonny’s looks like somewhere I’d never go.) I have to spell out “Sunny’s, S-U-N…” in order for maps to find the right location. I use Google Home to turn my lights on and off and check the weather. That’s not enough to justify a replacement cycle.

At the same time, I can open ChatGPT and ask the AI coach I created — simply by prompting and using memory — in-depth questions about my life, relationships, and existence on this planet. The answers it gives back are not only good, they’re insightful.

Even just sticking with the Maps use case, ChatGPT was also able to remember the name of a cool nightclub I went to in my twenties that no longer exists. My friends in NYC were reminiscing on old times over the holidays and I couldn’t remember Westway. (RIP.)

Exhibit 1: A real Q&A between me and ChatGPT about Westway

Me: “What was the name of the club on the west side highway that was setup like a strip club but wasn’t. In NYC.”

ChatGPT: “You’re likely thinking of The Box or Scores, but given your specific clue—“set up like a strip club but wasn’t”—the most fitting answer is probably The Westway. Here’s the breakdown.

• The Westway (2011–2015):

  • Located on the West Side Highway, in the Meatpacking District.

  • It was literally built in a former strip club, and kept some of that aesthetic—mirrors, poles, velvet booths—but was primarily a nightclub and performance venue, not an actual strip club.

  • Hosted wild parties, music events, and fashion week after-parties.

  • Attracted models, downtown creatives, and celebrity nightlife crowds.

Let me know if you’re thinking of a different era or vibe—there are a few other niche spots like Bungalow 8 or Veruka, but Westway sounds like the closest match based on your description.

But Siri can’t find Sunny’s? There’s a tragically massive disconnect between these two experiences and I believe it’s about to converge very soon.

Ive, who worked at Apple for 27 years — most recently as Chief Design Officer and widely considered the architect behind the iPhone — is leading the industrial design charge on what’s described as a family of AI devices at OpenAI: simple, unobtrusive objects meant to fade into the background rather than demand attention.

Based on a Perplexity search I ran this morning compiling the latest news, rumors point to OpenAI shipping their first device in late 2026 or early 2027. According to multiple leaks, they’ve completed initial prototypes of a pocket-sized, screenless device. Something like an iPod Shuffle. It’s audio-first, built around microphones, speakers, and possibly cameras, designed for ambient, context-aware assistance.

It also appears, based on news, that OpenAI is reorganizing internally around audio, consolidating engineering and product groups to improve next-gen voice models with more natural speech, interruption handling, and overlapping dialog—explicitly linked to the upcoming hardware. The hardware is expected to run OpenAI’s latest frontier models, ingest continuous environmental data (audio, visual) via onboard sensors, and sync with phones and laptops rather than replace them, acting as a “third core device.”

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My Predictions

I‘ve met with over twenty founders building AI assistants. So far I’ve invested in one (Jack) and spent six months building alongside the founding team on another in the coaching and expert advice space. As I write this, OpenAI announced it acquired Torch for $100M, marking a deeper push into healthcare. None of this is about hardware specifically, but it shapes my view on what the device will and won’t do initially.

I like the idea of a device that helps us be more mindful and off-screen. But will we trade screens for talking to a robot clipped to our shirt? Based on gut instinct above all else, here are my predictions on OpenAI’s hardware:

1. Use cases will follow ChatGPT’s adoption curve

I think OpenAI’s hardware will start with the core use cases people already rely on ChatGPT for: answering questions, explaining concepts, and capturing ideas through voice. The device will be ChatGPT in your pocket — listening, ready to help you think through problems or take notes while you’re walking, cooking, or commuting. From there, it will layer in services. Email and text composition. Calendar management. Food delivery through Uber Eats. Smart home control. Navigation and local recommendations… it will know where you are and what’s nearby. It won’t try to do everything on day one, but the path is clear with open APIs, etc.

2. Startups and vertical-specific use cases

I think OpenAI will face competition not from Google or Amazon, but from startups building for niche use cases: home management, childcare, education, elder care, etc. I also think that in many cases, these vertical players will win. The large infrastructure players can’t optimize for every context, and they shouldn’t try. The wedge is specificity.

3. Health data integration, not competition

I don’t think OpenAI will compete directly with Oura or Whoop, but I do think the OpenAI device will retrieve and output your health data on-demand. Voice query, instant answer. No app to open, no screen to unlock. The device becomes the interface layer for all your wearables — ask it about your sleep score, heart rate variability, or whether you’re ready for a hard workout. The data stays with the specialized hardware companies who do measurement well, but OpenAI owns the conversational access layer.

4. Voice-accessed app store

I think the device will access OpenAI’s app store entirely by voice. “Install the Montessori learning assistant.” “Open my meal planning app.” The apps won’t be visual; they’ll be conversational. This is the natural evolution of what we’re already seeing with ChatGPT plugins and GPTs. Developers will build specialized agents that run on OpenAI’s hardware, and users will discover them through natural language rather than scrolling through categories. The business model could write itself: OpenAI takes a cut of subscriptions, which startups will pay for distribution, just like Apple did with native iOS apps.

5. Three colors, just like the iPhone

And finally, I think the device will come in three colors, just like the iPhone. Ive knows that hardware isn’t just about function — it’s about identity. People will want choice, even in something meant to disappear. This seems trivial until you remember that color options signal that this is a consumer product, not a tech prototype. It’s a statement about mass-market ambition. (See OpenAI’s most recent ad campaign directed at consumers.)

Exhibit 2: Mike’s ChatGPT generated mock-up of OpenAI’s hardware

The Open Question

If not skeptical, I’m curious about adoption. Are people actually going to walk around talking to devices all day? Voice has always promised more than it delivered IMO. We’ve long had phone calls. We have voice notes. Yet text remains the dominant interface.

Everyone is about to have an AI assistant. What that assistant will actually do for us, and whether we’re ready to talk to it, is up for debate. The real question is whether OpenAI can create the first major platform shift since the iPhone launched in 2008.

Share This Life

Building my own venture capital firm has been the plan for some time. I bought the URL for Begin Ventures back in 2018 before the pandemic. The fund will be a natural extension to the deal-by-deal investing I’ve already been doing with Morgan at Backpocket VC.

Begin Ventures launched last week as a 506(c) fund. That means we can market directly to the public. Traditionally, VCs could not market publicly and limited partners (”LPs”) had to come via warm referrals. This is still largely the case. Regulation 506(c) has been around since 2013 but used by only a small fraction of VCs. Begin is among just a few new emerging funds more deliberately choosing to be public-facing. In order to invest, you have to self-verify that you’re an accredited investor. You can do that plus learn about Begin and see the types of companies we’re investing in here.

Begin blends what I’ve learned about analyzing, starting, and investing in companies since 2007. Our initial thesis is simple: the way humans live and interact with the physical world is going to change rapidly in post-AI society, and we want to back founders making day-to-day life better. Brian Chesky summed it up well on TBPN last month.

Here’s a clip of that interview here on Chesky’s Instagram.

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I plan to dive deeper into our thesis as we build Begin. Sectors we’re interested in investing include home, transportation, food, wellness, personal finance, and relationships. We will dabble in future of work as it relates to human sovereignty.

We plan to invest very early. Pre-Seed, first investor.

We’ll meet some founders through a fellowship we’re launching in 1Q26 meant to help founders explore ideas before they quit their current job. I happen to think that mid-career professionals with 7+ years experience are well fit to reinvent certain bits of the economy they know well. Other founders we’ll meet by way of ecosystem relationships we’ve built over the past ten years including other Pre-Seed funds, accelerators, studios, etc.

Going forward this newsletter will lean a bit heavier into investing. A journal of sorts. At only five posts in… I’ve grown tired of the polished style I previously created. Trying to fit my thoughts and ideas into the same format hasn’t worked for me, so I end up skipping.

Now, I’m going a bit more freestyle.

I’ll still write about coaching and what I’m learning. The self inquiry and personal growth — and sharing it with others — makes all of this worthwhile and more fun.

If we haven’t caught up in a while, I’d love to tell you more about what I’m building at Begin.

Here’s a link to my calendar.

Mike

Michael Saloio
Founder & Managing Partner
Begin Ventures

…And it ain’t electric so it’s way off. Send it back

Now playing: "E.B.I.T.D.A" (Ft. Pharrell Williams) by The Clipse

Yo,

This week I experimented with using Perplexity AI to discover articles from sources I might never have found otherwise. The results were fascinating.

Instead of my usual rotation of tech blogs and business publications, I stumbled across insights from places like Center Post Dispatch and Insider Inc. that offered fresh perspectives on familiar themes. It’s a perfect example of how AI tools can expand our information diet beyond our typical echo chambers, surfacing quality content from unexpected corners of the internet. Here’s what caught my attention this week at the intersection of investing in tomorrow and improving today.

Mike

This Week’s Stack

How AI Could Solve the Consumer Tech Slump, According to VCs (Insider Inc.) — Venture capitalists are betting big that artificial intelligence will revive consumer tech by powering a new generation of startups dedicated to making everyday life better. While consumer startups faced a downturn recently, funds like Premise Venture Partners and established names such as Andreessen Horowitz are ramping up investments, believing AI can enable companies to scale quickly and unlock new business models. The article dives into fresh subscription and ad-driven models, with examples ranging from AI-powered journaling apps to advanced health wearables. Read ›

Startups are strangely upbeat in 2025: AI may be the reason why (Center Post Dispatch) — Despite economic uncertainty, optimism among early-stage founders is soaring, particularly for companies that have made significant investments in AI. A Mercury survey of 1,500 entrepreneurs found 60% of AI adopters noted major improvements in financial confidence versus 28% for non-AI users. First-time founders and those in financial services are especially bullish, showing how innovation and mindset—fueled by technology—are powering resilience across sectors. Read ›

The great AI commerce startup opportunity, according to Andreessen Horowitz (Fortune) — A16Z partners Alex Rampell and Justine Moore break down the massive opportunity for AI in commerce. Their thesis: generative AI will revolutionize the way consumers shop, with assistants handling everything from routine purchases to complex buying decisions. They highlight how attribution and discovery are becoming battlegrounds for startups and detail why VC firms are patient but optimistic about truly transformative consumer AI businesses emerging. Read ›

Startup news and updates: Daily roundup (YourStory) — This daily roundup covers a wave of new founders building inventive tools and products designed to solve real-world problems and improve daily life. The piece spotlights funding rounds for social impact and life improvement apps—from AI-driven incident management to digital health platforms—underscoring a fresh energy and creativity among founders committed to “better living” at scale. Read ›

CEO of Lovable, one of the fastest-growing startups in history, at Disrupt 2025 (TechCrunch) — Anton Osika, physicist and founder of Lovable, describes building a consumer software startup with the vision to enable anyone to create apps just by talking to AI. Lovable broke records, reaching $100M ARR in under a year and raising at a $1.8B valuation. Osika’s masterclass at TechCrunch Disrupt 2025 highlights how rapid scaling, product focus, and category creation is redefining digital wellness and human creativity for a global audience. Read ›

Pro tip: Don’t have a news subscription? Insert the article links into ChatGPT and ask for a summary.

What I Learned This Week

Consumer is back — and AI is the catalyst. After years of consumer tech being declared “dead” or “too hard,” we’re witnessing a renaissance driven by artificial intelligence’s ability to solve fundamental problems that have plagued the space for decades.

What’s fascinating is how AI is addressing the core issues that made consumer businesses challenging: high customer acquisition costs, difficulty scaling personalization, and the complexity of building sticky engagement. The Mercury survey showing 60% of AI-adopting entrepreneurs feeling more financially confident versus just 28% of non-adopters isn’t just a statistic—it’s a signal that founders have found tools that actually work.

But here’s what really caught my attention: we’re not just seeing AI optimize existing consumer experiences, we’re seeing it create entirely new categories. Lovable hitting $100M ARR in under a year by letting anyone build apps through conversation isn’t just impressive growth—it’s proof that AI can democratize creation itself.

My thesis is that “life after AI” will be the golden age for both CPG and consumer tech because AI finally makes mass personalization economically viable. We’re moving from one-size-fits-all products to AI-native experiences that adapt to individual needs, preferences, and contexts in real-time. The Andreessen Horowitz piece on AI commerce gets at this—we’re not just talking about better recommendation engines, but AI assistants that fundamentally change how we discover, evaluate, and purchase everything from groceries to gadgets.

The opportunity ahead isn’t just about making existing products smarter; it’s about reimagining what consumer products can be when they’re built AI-first from day one.

Company I’m Following

Playground — In a moment when everyone seems to be chasing AI, and for good reason, we’ve been meeting some really interesting CPG companies.

One that caught my attention in particular, and that we recently invested in, is Playground; co-founded by Catherine Magee, Sandy Vukovic, and Christina Aguilera.

Catherine and Sandy are the operators—former executives at bareMinerals. They saw a massive gap in sexual wellness: no trusted brand actually built for women’s health across life stages. So they’re building what’s essentially “Hims & Hers, but actually for her.”

To me, what makes this interesting:

• GTM unlock. Bringing Christina Aguilera on as Chief Brand Advisor is driving brand awareness and keeping customer acquisition cost low (sub $10).

• Category opportunity. Sexual wellness is niche with no real brand leader, especially for women, and the category is moving from taboo to mainstream quickly. Playground is already in 400+ retail locations (Target, Nordstrom, Urban Outfitters), and expanding.

• Clinical expansion path. This is where it gets interesting. Playground is piloting clinical partnerships with platforms like Midi Health for subscription-based care. Their Miracle Melts product is moving through FDA 510(k) clearance as a Class II medical device—opening the door to provider protocols and reimbursement. Think Hims & Hers rolling out telehealth: Playground could do the same, embedding into OB/GYN workflows while building a digital experience that ties in health data. The shift from one-off retail purchases to continuous, medically-backed care is the real unlock.

Perhaps an odd thesis, but I think as AI frees up time and mental space, people are going to start investing in wellness even more than they are today.

If you’re interested in investing in early-stage startups, I’m a Partner at Backpocket. You can join our angel investing group get access to our full research report on Playground along with other companies we’ve watching.

Try This On

I’m going to share something that completely changed my daily experience: breathwork.

About a year ago, I started doing guided breathing exercises every day. The results have been significant—measurable improvements to my focus, stress management, and sleep quality. A heads up if you’re starting out: The first few times, my body got hot, then cold, and it felt like anxiety was coming. But I realized my body was letting go of stress and stuck energy. That initial discomfort passes quickly.

I started with 3-part breathwork from a coach, then discovered the Open app. The flexibility makes it sustainable: 5 minutes for a quick refresh, or 45 minutes for something deeper. Short sessions are mood-shifting. Longer ones can be almost psychedelic—you might learn some shit about yourself. The cumulative effects: deeper meditations, better sleep, higher energy. Controlled breathing activates your parasympathetic nervous system, literally rewiring your stress response over time.

Check out the Open app—beautifully designed with guided sessions from 3-20 minutes. I think it’s the best for getting started.

Start with just 5 minutes tomorrow morning. Pick a simple “energy” or “focus” session and see how you feel.

“In The Sun, In Good Times, In The Sun Bleaching”

Now Playing: “Soft One" – Yellow Shoots

Gregory Matthews, aka“Yellow Shoots” is a Brooklyn-based artist and producer I think you should get to know this summer.

Press play while you read.

Well,

Here's volume 3. Which ended up in a strange place.

I started this past week reading about a Republican NAVY Seal who transformed his life by taking Ibogaine in Mexico. This led me to Michael Pollan's piece in The New Yorker about religious leaders on psychedelics, too. Somehow I ended the weekend reading Warren Buffett's final letter to shareholders as CEO of Berkshire Hathaway.

If only Warren Buffett did mushrooms this whole thing would be a lot easier to tie together.

I thought about just scrapping this one. Like, what's the through-line? Where is this going? No one is going to care about the intersection between a transformed NAVY Seal, tripping priests, and the greatest investor of all time. A thought process that brought me to something else.

I think many of us have been conditioned to think we need to "pick a thing" and stick with it. (At least I have.) But it’s been my observation that creative breakthroughs happen when I let my mind wander between seemingly unrelated topics.

In the middle of my wrestling with this question, Rick Rubin’s latest newsletter dropped into my inbox:

The Creative Act: Thoughtforms & Innerworks

Follow the Pull

When focused, working on a project, we may get distracted, sidetracked. An inner battle ensues and we aim to avoid the distraction and stay on course. As counterintuitive and dangerous as it seems, sometimes the information drawing us outside of our purview might create a new way of thinking or a welcome break in the narrow mission we are on…

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a year ago · 56 likes · 1 comment · Rick Rubin

Following the pull, I decided to stop typing, open Instagram, and “doom scroll” with a new lens. It's just where my curiosity went — what might I find? No kidding, the first post I stumbled on was this:

I'll let you watch the video and read the post yourself. But to summarize: focusing on doing one thing really well is just one measure of success. What if instead your measure of success was "how much can I enjoy this?" This meaning your career, your life, your relationship(s), your whatever.

Thank you, Sir Richard Branson and Grace Beverley, for the reminder that some of us aren't built to focus on just one topic or go deep on one subject for an entire lifetime.

There’s something interesting about connecting the dots between seemingly disparate things, puzzle piecing them together in retrospect.

Mike

What I Read / Listened To / Watched This Week

1. Lawmaker 'Reborn' Through Psychedelic Therapy Wants the GOP to Embrace It (WSJ) — A bipartisan coalition is quietly advancing support for psychedelic-assisted therapy, especially for veterans and first responders. The article includes a powerful clip of Texas Republican Morgan Luttrell sharing how an ibogaine session in Mexico helped him heal both his PTSD and his relationship with his mother. Read ›

2. This Is Your Priest on Drugs (The New Yorker) — Written by Michael Pollan, this piece revisits a study from 2015 in which religious leaders—priests, rabbis, ministers—took guided psilocybin journeys. Nearly a decade later, the impact still resonates. It's a revival of mystery and direct experience in a profession built on faith. Read ›

3. Warren Buffett's 2024 Shareholder Letter (Berkshire Hathaway) — I read this one late this year, but it's always worth the time. It's likely his last letter as CEO of Berkshire, and it reads exactly how you'd hope: calm, sharp, and uninterested in hype. One stat that stuck with me—Berkshire paid 9 billion dollars in federal taxes last year, about 1/700th of all U.S. income tax revenue. Read ›

Pro tip: Don't have a news subscription? Insert the article links into ChatGPT and ask for a summary.

What I Learned This Week

The Veteran

According to a 2022 report from the Department of Veterans Affairs, 6,407 veterans died by suicide that year—nearly double the rate of nonveterans. In response to this ongoing crisis, a growing group of lawmakers, many of them veterans, are pushing for federal research into psychedelic-assisted treatments for PTSD, depression, and substance abuse. One of the most vocal advocates is Morgan Luttrell—a retired Navy SEAL and now a Republican Congressman from Texas—who in 2018 underwent a three-day psychedelic therapy session in Mexico involving ibogaine and DMT, both illegal in the U.S. He described the experience as transformative, helping him process trauma, save his marriage, and repair his relationship with his mother. He likened it to an "exorcism," marked by intense physical reactions and vivid visualizations that helped him "turn the page" on his life.

In 2023, Rep. Dan Crenshaw led a bill mandating federal research into these therapies for veterans and active-duty service members, with studies now underway at the Department of Defense and the National Institutes of Health. The Congressional Psychedelics Advancing Therapies (PATH) Caucus, co-led by Reps. Jack Bergman and Lou Correa, is also advocating for expanded clinical trials. Regulatory concerns remain with the FDA and others, including safety, efficacy, insufficient data, and challenges with trial design. While critics like Rep. Lauren Boebert raise concerns about potential recreational use, others—like Rep. Mariannette Miller-Meeks—have shifted their stance after hearing veterans' firsthand accounts.

The Priest

In 2015, researchers at NYU and Johns Hopkins conducted a study involving approximately 30 religious leaders from a variety of faith backgrounds, including Christianity, Judaism, Islam, and Buddhism. The participants were predominantly male (69%), white (97%), and Christian (76%). Each was given a high dose of psilocybin in a controlled clinical setting to observe its effects on spiritual life and vocational function. In follow-up assessments conducted months later, 96% of participants reported that the experience ranked among the five most spiritually significant of their lives. Approximately 79% said it enhanced their effectiveness in their work, deepened their prayer life, and enriched their sense of the sacred in daily experience. Many described encountering a divine presence that felt maternal or womb-like, challenging conventional masculine portrayals of God. Some reported visions or symbols from religions other than their own, which led to greater appreciation for interfaith connection. Several participants later became involved in faith-based psychedelic initiatives, applying their experience to religious education, pastoral counseling, and broader spiritual outreach.

The Investor

In his 2024 letter to shareholders—likely his last as CEO—Warren Buffett reported that Berkshire Hathaway paid $9.2 billion in federal income taxes in 2023. That's roughly 5% of all corporate income taxes paid by the 1,000 largest U.S. companies, or about one out of every 700 dollars collected by the U.S. Treasury from all sources. Buffett also noted that, between 2019 and 2023, the words "mistake" or "error" appeared 16 times in Berkshire's letters — an unusual level of candor compared to many public companies and other investment firms.

The Retrospective Through-line

Here's the thing I couldn't see while I was wrestling with this newsletter, sticking to the format of writing about what I read this week: the thread isn't about what these three stories have in common on the surface. The through-line is about how breakthrough learning happens.

A Navy SEAL discovers healing through plant medicine. Religious leaders find God in psilocybin. Warren Buffett admits his mistakes in public. These couldn't be more different stories.

But for me, looking closer, they're all about the same radical act:

the willingness to go where conventional wisdom might say you shouldn't.

The veteran stepped outside military protocol to heal trauma the establishment couldn't. The priests ventured beyond doctrine to experience the divine directly. Buffett built an empire on radical honesty, something many might think ignores the corporate playbook.

Each story is about someone who followed their curiosity into uncomfortable territory and discovered something on the other side. They didn't know where they were going when they started. The SEAL didn't plan to heal his relationship with his mother. The priest didn't expect to encounter a maternal God. I doubt Buffett set out to become famous for admitting his mistakes, or expressing gratitude to the corporate tax system for enabling his success.

I think the through-line here is about the willingness to wander. To trust that curiosity is its own kind of intelligence.

Try this on

Be curious. That's it.

Let your mind make connections that might not make sense until later.

What are you curious about right now? Go there.

Interesting intersections happen when we're not trying to force them.

Mike

“Tell the truth, don’t be afraid let your conscience be your guide.”

Now Playing: “Tell the Truth” – Otis Redding
Press play while you read.

Team,

Welcome to Volume 2 of This Life.

This week, I’m looking at where progress is unfolding quietly — beneath the headlines, inside existing systems, and in the conversations we often avoid but need to have if we’re going to build anything big.

We’ll look at an AI doctor for gig workers, drones delivering across US cities, a five-minute cancer treatment with no added cost to UK citizens, and a startup bringing personalized, preventative care to the workplace.

Plus: the generosity of telling the truth.

Mike

What I Read / Listened To / Watched This Week

1. 🩺 AI Doctor for Gig Workers — WSJ
   Akido Labs is rolling out AI-powered healthcare for ride-share drivers in NYC. Their ScopeAI system suggests diagnoses and treatments, which are reviewed by human doctors. It’s fast, remote, and built for people who’s livelihood doesn’t come with traditional sick days.

2. 📦 Drone-Delivery Is Real? — WSJ
   Zipline’s drone delivery network could quietly become a real player in logistics. The company has completed over 1.3 million deliveries in the US so far. It started with medical supplies and is now expanding to retail, reshaping how things move in cities.

3. 💉The Five-Minute 'Superjab' Treating 15 Cancers — The Times
   The UK just approved a five-minute cancer treatment that replaces hour-long IV infusions. The “superjab” delivers immunotherapy for 15 cancers, including lung, kidney, and skin. It’s faster, cheaper, less invasive, and comes at no additional cost to patients.

Pro tip: Don’t have a news subscription? Insert the article links into ChatGPT and ask for a summary.

What I Learned This Week

While we argue about tomorrow, others are building it today.

Not in debates or press cycles — but in five-minute cancer treatments. In AI doctors for gig workers. In drone deliveries that collapse distance and give people back their time in hours and energy.

The UK’s National Health System (NHS) rolling out life-extending care at no additional cost to patients is a reminder that systems and politics do shape outcomes. But the future isn’t being written on Twitter. It’s happening on the ground floor of companies and in policy change.

If we only look at the noise, we might miss the signal.

Company I’m Watching

Different Health is a pre-seed startup based in NYC rethinking how preventive care gets delivered. What makes their approach interesting is how they’re working within the system — partnering with corporations to bring proactive, data-driven care and performance-based coaching into the traditional healthcare model. (Think Superpower, Function, or Levels but built for employee populations.) By aligning with existing infrastructure, they could help prevention scale by meeting the system where it already operates.

Disclaimer: I recently invested in Different through Backpocket VC — a membership-based angel investing group I co-founded. We’re ~300 members strong and currently accepting new applicants. If you’re an accredited investor and want to co-invest alongside us, send me a note.

Try this on

It’s hard to build something great when everyone’s being “nice.”

Swinging for the fences means having the right team around you. Sometimes, someone isn’t the right fit right now. Or maybe they just need feedback they’ve never gotten.

That’s not good or bad — it just is.

Avoiding the truth doesn’t help. It’s not kindness, it’s control. And it’s actually kind of like… treating people small. It says:

“I don’t think you can handle this.” Or,
”I’d rather manage your reaction than be honest.”

Clarity creates movement. Vagueness keeps people stuck.

Try this:

Who in your orbit might deserve more honesty than you’ve offered?
Where are you collapsing being nice for being generous?

Open a new ChatGPT thread. Type:

“Help me give honest, kind feedback to someone I think isn’t the right fit — or just needs to hear the truth.”

Use it to prep for a conversation you’ve been avoiding. Be clear. Don’t overthink it. Just say your thing.

The truth doesn’t have to be heavy.
Most of the time, it’s just helpful — for everyone.

Peace out,
Mike

"And darling, our disease is the same one as the trees / Unaware that they’ve been living in a forest.”

Now Playing: “This Life” – Vampire Weekend
Press play while you read.

Hi friends,

Welcome to the first edition of This Life.

After a few years of writing under Mike’s Newsletter, I’m evolving my published writing to reflect a shift in my work and thinking.

To me, investing in this life is two-fold:

• It’s about investing time and capital into companies improving everyday life — in health, wellness, relationships, transportation, physical space, personal finance, and more.

• And it’s about investing in yourself — your mindset, your habits, your time, your relationships.

This lens is guiding the latest work I’m doing. More on that soon. But it’s also personal. I’ll share a few things I’ve read or learned, a company I’m excited about, and a practice to try on for yourself.

Same format. New direction leaning into healthcare, human systems, and what makes life better day-to-day.

What I Read / Listened To / Watched This Week

1. 🤖 Reid Hoffman shared a story about a Reddit user who used ChatGPT to solve a jaw issue they’d struggled with for five years — something multiple doctors had missed. The replies are full of similar stories. AI isn’t just about productivity; it’s already reshaping how we access care, advocate for ourselves, and improve daily life.

2. 🧬 How AI is Accelerating Drug Discovery. This explainer from MIT Tech Review dives into how large models are being used to find treatments faster, especially for rare diseases. A glimpse into where biotech is headed.

3. 💉 A16Z’s podcast on the science and supply of GLP-1s. A deep dive into how these weight-loss drugs are transforming healthcare, from patient care models to supply chain challenges.

What I Learned This Week

I think we’re entering an era where the most meaningful innovation won’t just make life more efficient — it’ll make it more human.

From a Reddit user diagnosing a chronic condition with ChatGPT, to AI accelerating rare disease research, to companies like Earth reimagining how we care for the dead, people are quietly reclaiming agency in parts of life that once felt outsourced, broken, or just daunting to navigate

IMO, this isn’t just tech disruption. It’s a shift in how we relate to systems that were built for a different time. The most interesting companies to me right now aren’t just building better tools, they’re giving people agency where they previously felt on the sidelines.

Company I’m Watching: Earth

Earth is a death care startup offering carbon-neutral funerals through human composting. Founded by two experienced operators from the traditional funeral industry, Earth is reimagining end-of-life care with a sustainable, full-service approach.

The company’s core product uses a proprietary “vessel” to accelerate the earth’s natural decomposition process using carbon, nitrogen, oxygen, and water — no fire, no emissions. In 30–45 days, the process transforms a body into one cubic yard of nutrient-rich soil that can be kept, used for planting, or contributed to forest restoration.

Customers can prepay like an insurance policy or pay at time of death. Pricing is below the cost of a traditional funeral, and the experience is fully managed online or at one of Earth’s facilities including licensed funeral services, transport, paperwork, and soil return.

On a quick personal note: anyone who’s had to make funeral arrangements, especially as a young person, can attest that the experience is less than desirable. Earth changes that.

While details on traction are limited, Earth is a Series A company with strong growth and a clear path in a massive, emotionally resonant market. What sets them apart is full-stack execution, handling every detail with dignity, transparency, and care in an industry long overdue for change.

Try This On

If your life were a startup, would you invest in it today?

Not the theoretical version five years out, but this week. The way you’re spending your time, energy, and money. Would you double down?

One practice I’ve learned this past year is auditing my calendar and spending and then marking each entry with a simple red, yellow, or green.

• Green = aligned with what I say I care about

• Yellow = neutral or unclear

• Red = draining or off-mission

It’s a fast gut check and a surprisingly honest mirror.

Try it: take the last two weeks of calendar events and expenses, and tag them red/yellow/green. Notice the patterns. What are you really investing in?

Thanks for reading. I aim to publish this weekly-ish — consistent enough to feel like a rhythm, with room for real life.

Until next time,
Mike

-Mike

🔖 My feed this week

I listened to Episode 409 of Invest Like the Best with Graham Duncan, titled "The Talent Whisperer" (originally aired February 4th.)

My favorite part was about “working with source,” a framework for building authentic work relationships. I found Duncan’s views on work, investing, and life to be refreshingly human and inspiring. I’ve been telling everyone about this episode, regardless of which industry they work in.

The episode made me curious to learn more about Peter Koenig’s Source Principles, so I dug deeper into Work with Source and discovered Tom Nixon’s work, which simplifies the concept. Highly recommend this simple yet powerful framework for anyone starting a new project.

I also read an investment memo about a company called Earth. Earth is transforming death care with carbon-neutral funerals and a better experience for loved ones. It’s cost-effective, better for the environment, and the market—made up of ~19,000 independent funeral homes across the U.S.—is ripe for healthy disruption. In a world where all the talk is about AI, I feel very little FOMO and am increasingly drawn to non-AI innovations like the built environment. There are still numerous opportunities to contribute time or capital to great companies reinventing tangible things—often in exchange for equity at more realistic prices.

🎼 What I learned this week

I spent a lot of time this week thinking about the concept of source.

Peter Koenig and the peeps at Work with Source define source as the person who takes the first action on any project—and therefore, the first risk. That first action could be anything: making a phone call, buying a domain, opening a bank account, or creating a deck.

According to Koenig, all project breakdowns stem from failing to recognize who the source is. It sounds almost too simple, but in my experience, it’s true. When source isn’t acknowledged—by the person who is source or by the project’s helpers (best exemplified in a founder-employee relationship)—things tend to go awry. We all have that friend who claims they could do it better than the founder. Maybe you’re that person right now. Or maybe you’re the source of your latest project but afraid to fully own the responsibility that comes with it. I’ve played all three of these roles, and truth be told, everything goes better when I know—and own—where I fit into the equation.

It would be easy to assume that being the source is an ego thing, but I think it’s the opposite. Being the source doesn’t mean you’re right or that you know more than anyone else. It just means you took the first risk—and because of that, you likely feel (and deserve) more financial and creative ownership over the thing you started. That’s fair, right? We can work with that, can’t we?

The best part about this source concept is that once you know where you fit in, you can find projects sourced by people you truly align with. And you can choose to bring your own life’s work—your own source—to the project.

Most of the time, we’re helpers, not the source—whether as employees, investors, consultants, or even just guests at a friend’s weird themed dinner party. (“Helper,” by the way, isn’t my word—it’s part of the Work with Source framework.) Either way, identifying and acknowledging the source—the person who stuck their neck out first—feels like a good way to minimize conflict. Because at the end of the day, you’re always free to throw your own damn dinner parties.

It’s been a year since I last hit publish here, and I’m excited to be back. Over the past year, my cofounder and I have been writing at Huddle Stories, diving into design, startups, and the future of work. But with a career transition underway, I felt like it was time to start writing here again.

The update: Huddle, the company I’ve spent the past four years building, was recently acquired by a private equity group. While not the outcome I initially imagined, I’m genuinely excited for this next chapter — one where I’m stepping out of the CEO role.

Here’s what I’ve come to terms with: I love inventing, investing, storytelling, turning ideas into products, finding early customers, pitching investors, and coaching. That stuff lights me up. What doesn’t? Operations. HR, accounting, policies, managing teams… it’s just not my zone of genius. And that’s okay. I used to feel like admitting that was some kind of failure. Now I know it’s just about playing to my strengths.

For too long, I stayed in the CEO role out of obligation — to my investors, my team, and honestly, to my own expectations. It took me nearly four years to even Google “Replacing myself as CEO of my startup” only to find Reid Hoffman’s article about his choice to step away two years into building LinkedIn. After a lot of reflection (and some nervous conversations), I finally told my investors how I was really feeling. Their response? “That’s incredibly self-aware. We wish more founders would do the same.”

Turns out, stepping aside wasn’t a failure — it was the most aligned, high-integrity move I could have made. It was true for me, and playing to my strengths is very likely the best thing for the company, too.

I’m now working to find Huddle’s next leader while dipping my toe into what’s next for me. I’ve started a venture investing club and fundraising advisory practice to scratch my itch for variety and help other founders navigate their journey. And I’m pivoting this newsletter to reflect my shift from operator to supporter of operators. Expect the usual personal reflections plus shoutouts to founders and companies worth watching, and, just for fun, a music pick in each post. Call this last bit an ode to Ben’s Blog. (IYKYK)

If there’s one thing I’ve learned in this transition, it’s that listening to your internal compass is everything. It took me longer than I’d like to admit, but I’m glad I finally did. Thanks for sticking around — I’m excited to share this next chapter with you.

-Mike

🔖 My feed this week

Zach Bell is building MyPlace, one of my favorite startups. I’ve been a fan and user since the beginning. I use the app to share my apartment with friends, and it’s the #1 tool that’s allowed me to travel and live in two cities while building a startup. Last weekend, Zach published my favorite piece on the election: “How is this even happening?” It’s about putting yourself in someone else’s shoes and getting curious instead of pinning them as [insert judgment of choice] for voting the way they did or believing what they believe.

🎧 Listen

My first startup was at Ryan Leslie’s at SuperPhone. This Fall marks the 10th anniversary of meeting Ryan and joining his company. Four years before, his album Transition was nominated for Best Contemporary R&B Album at the 53rd Grammys (2011) — an album title fitting for this particular post.

I took the past two months off from writing this newsletter to focus on other things. Heading into Autumn here in NYC, and having just passed my 39th birthday, I feel inclined to start sharing again; on that back-to-school, Autumn in NYC vibe.

I recorded the 4th episode of Huddle’s podcast Lone Geniuses a few months back. We dropped it last week, and I’m re-sharing it here. It’s appropriately titled Writing Your Own Narrative and features Laura Gao.

I love when people do things their own way. Laura is one of those people. She didn’t pick a major in college because she didn’t get why she’d need to. She started drawing comics just because she liked it. She weaved data into her work because it interested her. And she walked away from her full-time Product Manager career in Big Tech to make art and tell stories—starting with a heartfelt tale about her hometown: Wuhan, China.

During the COVID-19 pandemic, and as a response to the growing Sinophobia surrounding the virus, Laura wrote short comic The Wuhan I Know. It took off on Twitter, going viral and becoming the basis for the graphic memoir Messy Roots, landing Laura a book deal to write four more.

Sometimes, the key to creating something great is to respond thoughtfully and authentically to something not so great. You can listen to the full episode below.

Have a great weekend,
Mike

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🔖 My feed this week

Lone Geniuses

Episode #004: Writing Your Own Narrative

This episode's guest is Huddle member Laura Gao, a Silicon Valley Product Manager turned artist. She's best known for her short comic The Wuhan I Know, which she wrote in response to the growing Sinophobia surrounding the COVID-19 pandemic.

In this episode we discuss:

• Transitioning from Silicon Valley to writing, comics, graphic novels, and more

• Writing and art as a means to better mental health

• Taking a stance on Sinophobia and going viral on social media

• How to own your career as a full-time artist and maker

• Designing a creative schedule and plan that works for your own unique path

Somehow I slid into a podcast with the likes of Seth Godin.

A few weeks back, I took a right on South 4th Street, left on Bedford, and walked to David Nebinski’s home, just down the street from my apartment in Williamsburg, BK. Upon arriving, I learned that David and I have the same birthday (year and all), and both started our careers in equity research.

David has a podcast called Portfolio Careers. I think we were supposed to talk about having varied interests and building a portfolio career. Instead, during episode #276, I went on a tangent about relationships.

When I was working with Ryan Leslie on SuperPhone, we spent a lot of late-night work sessions jamming about the concept of 1,000 true fans. Coined by Kevin Kelly, 1,000 true fans is, in a nutshell, the idea that no one needs 1M Instagram followers to build a career. Instead, we need 1,000 people who, for lack of a better way to say it, genuinely f*ck with us. The early adopters who will purchase whatever we’re selling. (I think I’ve just inadvertently connected the dots between me and Seth Godin.)

My conclusion from all these work sessions on true fans was that my life consisted of my relationships—the people I interact and communicate with the most. And if there were a place that could visually represent what my life looked like, it was inside of my text feed. I could scroll through my texts and see exactly what I was up to. And even if what I was up to wasn’t something I cared to admit, it would always be 100% true.

If you want to make music but have no music friends on iMessage, you’re probably not making music. (This one rings true for me.) The same goes for starting companies, writing books, dating, and more.

So what are you creating on text? Are you generating awesome sh*t or fun with friends? Connecting with family? Building something? Or are there a few conversations that are spinning lightweight drama and not serving the grander mission you’re on?

It can be a tough pill to swallow (it’s certainly been for me at times), but the answer to how you’re spending your time and how to change it lies right inside those blue bubbles. And by god, I’m not saying to go out and cut people out of your life. I’m simply suggesting that if you want to change your life, a good place to start is with who and about what you’re texting.

Peace out,
Mike

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🔖 My feed this week

Portfolio Career

Episode #276: Building Relationships and Huddle

Episode Notes (by minute):

• 1:30: How hosting dinners helped build relationships and to some extent where Mike is now as the Cofounder of Huddle

• 3:15: “I really believe that life is lived in relationship. So if you want to change your life, you really do have to change the people you talk to every day.”

• 7:00: How Mike is intentional about the people in his text feed, and why you may need to cut some people from it

• 9:00: “through your relationships is how you will create whatever you want to create.”

• 10:30: How you could start hosting dinners by starting with your closest friends first

• 17:30: How being coached is helped Mike a lot through accountability 

• 21:00: 3 trends that Mike is seeing about startups and flexible work: people are leaving big tech to freelance, those same people are starting businesses, and people being more open to building their company flexibly

• 28:00: How ~25% of the Huddle community has W-2 full-time job

• 31:00: How Mike holds himself accountable to X amount of messages per day and setting up meetings with people. 

• 36:00: How Mike wishes that he would’ve stayed in touch with people in his network

• 39:00: How Mike has gotten a lot of value from journaling daily

Listen to Portfolio Career on Spotify below.

We shipped our third episode of Loan Geniuses — a podcast where I interview members from the Huddle community to learn about their lives and careers. If you haven’t listened, it’s like a “Behind the Music” for creatives.

The fourth episode features Huddle investor and Snapchat designer Stephanie Engle. Steph is a designer, entrepreneur, photographer, competitive equestrian, and more. I learned a lot from talking to Steph about building a portfolio career, following your passion, and getting into rooms with people that make you uncomfortable (in a good way.) The whole episode, along with key snippets, are linked below.

Have a great weekend,
Mike

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🔖 My feed this week

Lone Geniuses.
Episode 3: Be Around People Who Make You Sweat with Stephanie Engle

This episode's guest and Huddle investor, Stephanie Engle, is best known for her role as a product designer at Snapchat and as an angel investor in product-driven companies. Before Snapchat, where she works mainly on AR experiences, she worked at Airbnb, was the first product designer at Cruise Automotive, designed interfaces for self-driving cars, and started her career in Silicon Valley at Facebook, creating VR experiences. 

Michael Saloio Instagram, LinkedIn, Twitter
Stephanie Engle Twitter, LinkedIn, Instagram
Huddle Website, Instagram, LinkedIn, Twitter

Listen to episode 3 on Spotify below. Catch it everywhere else here.

🎶 What I learned this week

Here are just a few quick takeaways from my chat with Steph.

1. "Be around people who make you sweat." I.e., surround yourself with people who make you just a little uncomfortable because they're so good at what they do that you're forced to step it up and play bigger.

2. "You're always closer than you think." We're typically only 1 or 2 people away from that dream job, the perfect investor, new hire, or person who'll make a key introduction and shift your life's trajectory. This one has been especially true for me. I met Ryan Leslie bc I attended an event I almost decided to bail on and sent a cold email afterward. Stephanie Golik found me on AngelList randomly back in 2015. The impact and number of other amazing people I've met through just these two people is ridiculous - Danny Quick, Nathan McCartney, Samir Rayani, Stephanie Engle... the list goes on and on. Naming just a few here, but you get the idea.

3. Having a "portfolio career" can boost creativity. Steph does *a lot* of different things - photography, Airbnb hosting, competitive horseback riding, investing, entrepreneurship... all in addition to being a designer at Snap Inc. We don't have to limit ourselves to picking a thing. In fact, outside endeavors can make us better and more creative in our primary careers.

Happy Sunday, Father’s Day, Birthday to Steph, Juneteenth, Long Weekend, Summer Solstice… All of it. There’s much to acknowledge, celebrate and be grateful for this weekend. So let’s have some fun ya?

Speaking of which, we shipped our second episode of Lone Geniuses a few weeks back with Emily Grubman—and it’s all about optimizing work for fun.

Emily has low-key named a lot of the products you know and love. She worked at Red Antler in branding and decided the thing she liked best was naming things. So now that’s all she does. Why? Because, in her words, it’s the exercise that’s most fun. Simple. Love it.

Full episode below. Listen by a pool somewhere.

Mike

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🔖 My feed this week

Lone Geniuses: Episode 2: Optimizing Work for Fun with Emily Grubman

Our next guest is Emily Grubman. Emily is the Founder of Title Case, a consulting company that focuses entirely on naming. Before starting her own business, Emily spent nearly six years at Red Antler working on some of the biggest DTC brands in the world. She became the firm’s naming expert, naming companies like Prose, Burrow, and more.

What I love about Emily’s career path is her focus on work that’s fun. She picked naming because it’s the thing she liked doing the best. And as you’ll learn, Emily has a knack for finding the right rooms to be in and keeping it honest and authentic with the people she meets.

Her story is also about persistence and grit. She lied about her address being in NYC to get her first job before moving to the city, and she paid the bills in her early career days as a tasker on Task Rabbit, waiting in line for people who wanted to go to Shakespeare in the Park.  

Listen to episode 2 on Spotify below. Catch it everywhere else here.

🎶 What I learned this week

Fun as the compass.

Just a provocation this week and that’s it. What if instead of analyzing, managing, strategizing, or following some pre-determined societal path, you trusted fun as the compass? Or perhaps joy, satisfaction, excitement… Pick a word that suits you and gives you energy and optimize for that this week, instead of “trying” to get your next move “right”.

I haven’t written much over the past few weeks. Lucky for me, a friend has. Andrew Hutton published "Huddle and The Fractional Team Revolution—a deep dive into what we’ve created at Huddle: the article plus some learnings about creating vs. reacting below.

Mike

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🔖 My feed this week

Huddle and The Fractional Team Revolution (full article here.)

During the pandemic in 2020, Andrew and I were more than kicking around ideas for companies. We had MVPs and early users for two similar ideas: his, an educational program for early-stage founders to get the resources they needed to get started from “Day One,” and mine, a network where any founder could connect and “Huddle” with HQ talent fast.

We were close to combining the two companies but ultimately decided they should be separate—Day One and Huddle were born around the same time.

Thanks, Andrew Hutton, for sharing my story with my cofounder Stephanie Golik and our journey at Huddle. Read Andrew’s first startup deep dive as part of his Future Founders series here. Grateful to have excellent partners like Day One from, quite literally, day one of our startup journey.

Full Tweet thread here

🎼 What I learned this week

Creating vs. reacting.

You might have heard it called expansion vs. contraction, love vs. fear, or abundance vs. scarcity. It all comes down to the same idea; we have a choice at every instance of life—create or react.

Our nervous system knows the difference. Everything feels tense, frantic, and even painful when reacting/contracting. Creating and expanding, on the other hand, has a light, free, energizing quality.

Two weeks ago, I kept a journal of everything I did for one week. Don’t freak out; it wasn’t that hard. I just wrote down what I did on one side of a sheet of paper, and on the other, I wrote whether the activity felt energy-producing (i.e., creative) or energy-draining. The results surprised me.

Of all the draining tasks on my list, there were only three key buckets: (1) unplanned meetings, like an impromptu brainstorm, (2) answering messages and emails when I had planned to do something else, and (3) meetings that started late or went over. Every energy-sucking task was due to one thing: unintentional time—reacting to whatever was thrown my way instead of planning my day and using my time productively

I think it’s true that “discipline is freedom.” We can’t create what we want in life when we’re spending time not creating it.

🧰 Try this on

Write down everything you do for one week. On the left side, list the task—preferably while doing it. On the right, write whether the activity felt generative or draining. You might find just a few common themes.

Here’s the kicker: draining tasks aren’t wrong—they show us where to be creative. Can you delegate the task? Reinvent it? Is the job no longer serving you? Is your time spent getting you to where you want to go?

More audio this week 🎙️. We started a podcast at Huddle.

I’m excited to introduce Lone Geniuses, an audio show that uncovers the work and lives of the people behind the products and brands you love. It’s an outlet for creatives and builders to tell their stories, and the stories so far have been nothing but remarkable.

On the show, we debunk the lone genius myth. Creativity only happens inside a community. This is a show about making things together.

Members of Huddle came up with the name, including Andrew Stotzko of the Make Things that Matter podcast, Emily Grubman, who worked at Red Antler and now runs a naming consultancy, and Lori White, who helped create the brand at Huddle and elsewhere.

Our first guest is Daniel Batten. Dan is currently Creative Director at Hims & Hers. Before that, he helped create and incubate consumer startups as part of the Gin Lane and Pattern Brands teams: companies like Sweetgreen, Harry’s, Stadium Goods, Quip, Haus, and more.

This episode is for anyone wanting to know what it’s like to take a casual passion and make it big simply by following your gut.

Mike

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Lone Geniuses: Following Your Creative Intuition with Dan Batten

Dan’s path to creating brands for some of the fastest-growing companies was paved by trusting his creative intuition. He started his career as an amateur photographer. His tinkering with photos and videos led to an interest in motion graphics design, eventually landing him a job at Gin Lane. One of his first-ever design projects won an award.

During the episode, we talk about Dan’s life, how he got his start, and how he unlocks space for creativity. My favorite part of the conversation is when Dan talks about using anxiety as a tool. Enjoy.

Listen to episode 1 on Spotify below. Catch it everywhere else here.

🎼 What I learned this week

Stop explaining your moves and move.

I’ve recorded three episodes of Lone Geniuses so far. Movement is the common thread amongst all three guests in turning passion into work.

I’ve always loved audio and grew up in a family of musicians. My relatives on both sides of the family are music teachers, composers, and artists. The Saloio Family Band played the gazebo in my hometown, marched in parades, sang in church, and got together once a week to play classical music.

Growing up, I never really embraced it. I dabbled in the saxophone and drums, know a little guitar, and started taking piano lessons last month. My natural curiosity, however, has forever been production. I’ve always seen myself as the one putting the pieces together rather than being any one piece myself. Unsurprisingly, I build teams for a living.

Three years ago, I took up music production as a hobby. A small win—I produced everything you’ll listen to on Lone Geniuses: including the short opening track 🎶. I didn’t know we’d ever do a podcast at Huddle when I started learning Ableton. Huddle wasn’t even born yet.

Having this new creative outlet has been rewarding and fun. I’m glad I started. We never know what outcomes are on the other side of our moves. So why spend so much time debating them, anyway?

Thanks , Nigell Barlis, Rion Harmon, and Stephanie Golik

This week I’m bringing you another podcast I was lucky enough to be a guest on - Make Things That Matter.

I met Andrew Skotsko, the show’s founder and host, after he joined our builder community at Huddle. Our conversation bounces around with one central theme: the higher you go, the higher we all go. We talk about meditation, leadership, and the concept of ubuntu.

I’m starting to really like this audio stuff. More to come

Mike

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Make Things That Matter on Spotify

“This is a candid conversation about leadership and how our egos, sense of identity, and personal practices shape our company cultures. In particular, I think you’ll find practical benefit from our discussion about decoupling the concepts of morality and integrity to have healthier team dynamics.”

Listen to Make Things That Matter Everywhere Else

The Really Rich Podcast with Nicholas Crown is one of my favorite new listens (scroll down). Thanks to my good friend Harrison, and a bit of serendipity in Miami, I got to join the show a few weeks back. The episode dropped this past week.

Nicholas is a prior Wall Street trader who gave it all up to pursue his dreams—his ride isn’t for the faint of heart. A Cornell grad, Nicholas quit finance to pursue a career in music. He played at Bowery Electric and other similar-sized venues, but his go as an artist fell flat, and he found himself working in a retail store.

Since meeting him, one of the biggest things I learned from Nicholas is: you don’t get to decide what the world wants from you. Nicholas wanted his work to touch millions of people, but his music wasn’t getting it done. Instead of quitting, he pivoted his calling as a creator to comedy, and his “Rich Guy” vs. “Really Rich Guy” characters blew up on TikTok. It turns out, what was most authentic to Nicholas, and what landed with millions of people, was making fun of his old life on Wall Street. The Rich Guy is a jerk who values status and money above all else, while the Really Rich Guy is a kind-hearted human who understands that life—and getting wealthy—is about treating everyone well and creating value for others.

Fast-forward to today, Nicholas Crown on TikTok gets 30M+ views per week! His large audience has allowed him to ink brand partnerships with companies like Fundrise and Public. He recently started a software company to help other creators monetize their audience. And his podcast lets other entrepreneurs share their journey through candid conversation—your boy is episode #9.

During the episode, Nicholas and I talk about the power of sending a cold email, team building, failing, developing your authentic style, and more.

Hope you enjoy it,

✌️Mike

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Team Building, Startups, & Hitting Rock Bottom (The Really Rich Podcast)

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