Preston Smalley (@prestons) profile picture

Product & Tech Leader with background in digital TV entertainment, two-sided marketplaces and mobile apps used everyday by millions of people.

Silicon Valley, CA
Joined May 2008
Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)Photo by Preston Smalley (@prestons)
Preston Smalley retweeted
The most female-led product org in tech right now: Chief Product Officer: Ami Vora Claude Code/Cowork Head of Product: Cat Wu Claude Code/Cowork Head of Eng: Fiona Fung Claude Platform Head of Product: Angela Jiang Claude Platform Head of Eng: Katelyn Lesse Research Head of Product: Dianne Penn President: Daniela Amodei (Also, the fastest-growing company in history)
30 mins into the claude code keynote and every speaker so far has been a woman. just saying 🫶🏻 @asvora @angjiang @katelyn_lesse @_catwu Dianne Penn @claudeai
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Preston Smalley retweeted
Say “Howdy” to almost everything you want to watch at an unbeatable price. Commercial-free TV is now just $2.99 a month.
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Preston Smalley retweeted
Most companies prioritize features based on customer problems alone. But the best product companies—Apple, Amazon, Stripe, and others—do something fundamentally different. They practice "product shaping." The traditional approach: Identify customer problems → Prioritize by importance → Build solutions → Hope they work well The shaping approach: Identify customer problems → Prototype rough solutions → Prioritize based on both problem importance AND solution quality This changes everything. Instead of betting your roadmap on abstract problems, you're betting on concrete solutions you can actually evaluate. Take Apple's famous multi-touch story: Jony Ive's team spent years prototyping a touch interface for tablets in the lab. When Steve Jobs saw it, he realized it would be better for phones. They shelved the tablet, prioritized the iPhone, and changed the world. That's product shaping at its finest. So why doesn't everyone do this? Simple: Running a prototyping lab that builds dozens of concepts that never ship is expensive. Most companies can't justify the cost. But AI prototyping is changing the game completely. What once required months of engineering time and significant budget can now be explored in hours or days. Teams can rapidly shape solutions, test concepts, and make roadmap decisions based on real prototypes instead of wishful thinking. The barrier to product shaping is disappearing. And the companies that embrace this shift will build better products, faster than ever before. Are you shaping solutions before you prioritize them?
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Preston Smalley retweeted
I made it to Amazon VP because my managers fought for my promotions. They fought for my promotions because I met the 3 criteria that a manager needs to risk their reputation on you:
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Preston Smalley retweeted
Worthy Read: AI Can Synthesize Data for You—But Should It? by Christina Wodtke "When AI does the synthesis, you skip an essential part of the process. You don't inhabit the data." 🤖 Want to build better product intuition? It's not about AI-generated reports—it's about getting your hands dirty with the data. This article explores why physically engaging with information helps you develop deeper understanding and better gut instincts. What you'll learn: 🧠 How "inhabiting the data" rewires your brain 📝 Why Post-its remain powerful thinking tools 🔍 The role of physical interaction in processing information ⚡ How to use AI as a tool without sacrificing deep understanding Key practices for building product intuition: 🔮 Watch people interact with products 👀 Notice where users hesitate or smile ✏️ Take notes and draw diagrams 🔄 Move ideas around physically Read the article: buff.ly/BzCae6R 💭 When was the last time you felt the difference between just seeing an insight versus truly feeling it? Share your thoughts in the comments below.
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Preston Smalley retweeted
Knew he could revive us.
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Preston Smalley retweeted
You’re exhausted. You want to quit. Instead, say these two words to yourself: “Five more.” Here’s the reason it keeps you going…
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Preston Smalley retweeted
I've always wanted to know which companies create the best product managers. I finally have answers. I teamed up with @GotLiveData to see which companies’ PM alumni go on to see: 1. The most promotions 2. The fastest immediate promotion 3. The fastest rise to leadership roles (e.g. to VP, CPO, Head of Product) 4. The highest rate of becoming CPOs and Heads of Product 5. The highest rate of becoming the first PM at another company 6. The highest rate of becoming founders Out of this, we triangulated a list of top 10 companies that create the biggest inflections in the careers of their PM alumni. Here's the list: 1. @RevolutApp 2. @n26 3. @eBay 4. @Plaid 5. @Intercom 6. @Intuit 7. @LinkedIn 8. @PalantirTech 9. @Deel 10. @Discord Here's the full post with all of the data and analysis: lennysnewsletter.com/p/which… My biggest surprises and takeaways: 1. The top two companies are based in Europe! One in London, one in Berlin. Go Europe! 2. Fintech is dominant—5 out of the top 10 companies! Did not expect that. It’s probably no coincidence that the PayPal mafia has been so successful. One explanation, shared by my buddy Dennis Yang (PM at Chime), is that fintech nurtures strong product leaders because fintech work is on hard mode—lots of risk/fraud vectors, difficult stakeholders (e.g. compliance, regulations), and endless complicated tradeoffs. Another explanation could be that fintech PMs leave to join other fintech companies or start fintech startups, and since they know that space well, they’re more likely to thrive. 3. We have a new set of startup mafias: Palantir, Plaid, N26, Ramp, Intercom, Revolut, Duolingo, Uber, Notion, and Coinbase. The standout company is Palantir, where almost a quarter of Palantir PMs went on to start their own company. Almost a fifth of Plaid PM alumni went on to start a company, which is also incredible. Of older and larger companies, LinkedIn, Google, Intuit, and eBay made it into the top 15. Impressive! Props to LinkedIn for being the most founder-friendly big company. 4. FAANG companies lag behind. eBay, Intuit, and LinkedIn are far ahead of companies like Microsoft, Google, Apple, Meta, and Amazon in these lists. One explanation is that PMs at FAANG companies learn how to operate well within that specific company and are less successful elsewhere. Another explanation is that the best PMs at FAANG companies are happy and don’t leave, and so we don’t see their trajectories in the data. 5. There are an equal number of B2B and B2C in the top 10. You can do great no matter which direction your career goes. Notable mentions: 1. @TryRamp (~800 employees, founded 2019): Particularly strong at creating founders—which is extra impressive since it’s so young. - Ranked 3rd at founder rate - Ranked 5th at first PM rate - Ranked 10th at time-to-next-promotion after leaving 2. @Nubank (~7,000 employees, founded 2013): Strong all around but not ranked highest on any specific dimension. - Ranked 6th at Head of Product rate - Ranked 7th at first PM rate - Ranked 8th at fastest risers - Ranked 9th at fastest promotion 3. @NotionHQ (~500 employees, founded 2013): Especially strong at creating first PMs at other companies. - Ranked 2nd at first PM - Ranked 4th at CPO rate Don't miss the full post with tons more: lennysnewsletter.com/p/which…
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Preston Smalley retweeted
If you want to consistently underpromise & overdeliver externally, you’d be smart to foster a culture that makes it okay for your team to overpromise & underdeliver internally. Most likely your competitor thinks this is a preposterous idea. Therein lies your advantage.
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Preston Smalley retweeted
The choices are endless. And the Backdrops are yours. 🖼️
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Preston Smalley retweeted
Roku's MLB deal is now official. It will carry Sunday morning games, starting this Sunday with Red Sox-Cardinals. Multi-year deal also includes nightly clips delivered as VOD and available in MLB Zone/Sports Zone plus an MLB FAST channel.
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Preston Smalley retweeted
Here's the secret of the most charismatic people in the world... The 3 Levels of Listening:
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I won't lie, I: • Watch Netflix • Drive nice cars • Eat Avocado Toast • Don't wake up at 5 AM • Drink Starbucks 2x per day • Spend too much on vacations And, I'll still retire earlier than 99% of people. Forget their "rules". These 19 thoughts WILL change your life:
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Preston Smalley retweeted
If you are looking to make a difference this holiday season supporting families suffering from food insecurity, check out our campaign page @DaffyGiving. TY to @reidhoffman, @schrep, @gokulr, and @jdh for running matching campaigns across the Bay Area. daffy.org/feedbayarea
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The holy grail of parenting is consistency. Every parent wants to be consistent in how they raise their kids - consistent values, consistent responses, consistent discipline. That's why I always advise parents to "find your distant mountain." In the natural world, a distant mountain is a reference point. It rises above the landscape to orient you. You know where you are and where to go next. In parenting, it’s a metaphor for developing a long-term vision for your kids. As parents, we get so trapped in the day-to-day demands of raising kids that we miss the larger story. Having a written vision for your kids keeps you oriented when all feels lost. Here’s how to develop one: Pick a Destination Imagine your kids at a certain age. There’s no magic number, but I’ve always chosen 40. The trick is to find something far off into the future (a distant mountain). The goal in parenting isn’t to raise an awesome 4 year old. You’re raising a future adult, so think in those terms. Define the Mountain This is where the work gets done. I always encourage parents to start with 5 simple questions. When my child is 40: - What’s important to them? - What motivates them? - What words do I hope describe my relationship with them? - How do other people (spouse, friends, coworkers) describe them? - When things go wrong in their life, how do they respond? What anchors them? None of these questions provide a full picture, but they get our hearts dreaming. When you’re dreaming about your kids, dream about the kind of people you want them to be - who over what. As a parent, I’m always excited for my kid's accomplishments, but I’m most proud of who they are as people. Think in terms of character, qualities, and virtues rather than academic, material, or social accolades. Make A Map Next, distill your dreams out into statements. These will typically be positive statements, but there are times where negative statements are just as helpful. They’ll sound something like this: I will raise children who find joy in serving others. I won’t raise children who are controlled by fear. Write these statements down in a journal or some other place where you can refer to them. Follow the Map Here’s why I’ve found this process so powerful. If you know who you want your child to be at 40, you can back your way into how to parent them at 4. For example, I will raise kids who do the right things for the right reasons. Which means, I don’t want them to clean their room because I’m threatening or forcing them to. When they resist cleaning their room, it’s my job to explain why it's important. It doesn’t mean they’ll jump up and do it with a smile on their face. But I’m planting values in the fertile soil of their heart that I hope will take root over time. Developing a big vision for your kids is as much for you as it is for them. In the demands of daily life, it’s easy to lose our way. To be consistent as a parent means you’ve got to have a clear, actionable vision for the child you're raising. Finding your distant mountain helps you know you’re moving in the right direction. *** I'm David and I write about being more thoughtful as a spouse, parent, and business leader. Follow me @wdmorrisjr for more content like this.
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Preston Smalley retweeted
One of my core AI workflows: 1) Find audio/video I want to learn from 2) Transcribe it using @descript 3) Download .docx file of the transcript with time stamps and speaker names 4) Upload to @AnthropicAI’s Claude web interface 5) Chat with Claude to get learnings
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Preston Smalley retweeted
The making of “Under Pressure” was total serendipity. In 1981, Queen and David Bowie were recording separate projects at Mountain Studio — which was owned by Queen — in Montreux, Switzerland. The group’s producer David Richards popped over to Bowie and asked if he wanted to jam. They all got boozed and decided to make a song together. Queen drummer Roger Taylor had penned some lyrics but Bowie took the songwriting lead and sprinkled his magic. The “Under Pressure” collaboration was an instant hit when it came out in October 1981 (author’s note: this song goes hard AF). However, Bowie never got to perform the song live with legendary Queen frontman Freddie Mercury. They were both present at the Live Aid Concert in 1985, but Bowie wasn’t able to jump onto the Queen set. In 1992, Bowie did get to perform a live event with Queen for a Freddy Mercury Tribute concert (Annie Lennox sang Mercury’s part). This video stitches those two performances to show Bowie and Mercury singing on stage “together”. Legends.
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Preston Smalley retweeted
you don’t present multiple product design options to give stakeholders a “choice”. you present multiple design options to make it clear which one is the best path forward & why.
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