The Best Books and Articles I Read in 2019

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2019 was a huge year for me.
I rediscovered nature, recommitted to writing, experimented widely, scuttled many things that have weighed on me for years, and greatly improved my overall investing. Most important, I deepened my relationships with my family, my girlfriend, her family, and my closest friends more than in any previous year. 2019 was a year of surprising business growth. But more surprising still, it was a year of developing a greater sense of inner peace, and the two have rarely come together in my life.
Much of this wouldn’t have happened without reading the right things.
In the information game, the race doesn’t go to the swift, it goes to the selective.
This post will share the most impactful articles and books that I’ve read in the last 12 months.
First, a few notes about how I read, keep track of things, and review highlights:
  • I save all articles to Evernote using the web clipper (often as a “Simplified Article,” which strips out images, ads, etc.), then I read the articles and add ** and bolding to any sentences, quotes, or passages I find most insightful. Later, this allows me to use Command-F to quickly find *** in any document and review my highlights in minutes.
  • I read nearly all books in Kindle format when possible. This permits me to highlight a book, after which I can go to my Amazon Notebook on a laptop (here’s a sample screenshot of mine) and once again pull all of my highlights into Evernote in a relevant notebook (Investing, Home and Design, etc.). Next, and this should sound familiar, I add *** to my favorites in a second pass. Note that some publishers have strict export limits (publishers, this makes it hard for me to promote your books, by the way), so you should highlight 1–2 chapters as a test first, then see if your highlights are truncated in your Amazon Notebook.
  • Another great option for revisiting your highlights is Readwise, which I’ve been using more and more. This tool was introduced to me by my close friend, Mike, who described it thusly: “Basically, you integrate with Amazon [Kindle], and it sends you a digest every day of 5 to 15 of your past highlights from a random selection of books. […] It also integrates with Instapaper and Highly so you can grab text from the web. Nice and simple.” As the homepage asks: “Highlighting is great, but what’s the point if you’re never going to see any of those highlights again?”
  • For books that I have to read in paperback or hardcover, I create a handwritten index in the front of the book using this approach. I first detailed this process in 2007, and things have changed very little. The only additions: I will now save photos of the index to Evernote, and I’ll sometimes have an assistant scan the entire book to preserve my highlights. Oh, I also had more hair in 2007, and one would hope that I’ve matured a bit over the last 13 years.
Next up, we have two juicy lists:
  • “What I’m reading” descriptions from most weeks in 2019
All of the “What I’m reading” descriptions are taken from the free newsletter that I send out every Friday, “5-Bullet Friday.” It’s a short email of bullet points that describe the five coolest things I’ve found or explored each week. “5-Bullet Friday” often includes books, gadgets, experimental supplements, tricks from experts, and weird stuff from all over the world. Once again, I’ll be sending these out on Fridays in 2020. To subscribe and join 1.5+ million other folks, please click here. It’s easy to unsubscribe anytime.
After the “What I’m reading” entries, I’ve copied and pasted nearly all of the books that I purchased on Amazon in 2019. Many of them didn’t appear in “5-Bullet Friday,” even though they had a big impact. [Pro tip: To look at your own books from 2019, you just need to search “books” under your Orders in your Amazon account.] As I do in Evernote, I’ve added *** next to those books that were particularly helpful or interesting to me.
I hope you find this review useful. Enjoy!


What I’m reading (January 18, 2019) Surge Cities: The 50 Most Startup-Friendly Places in America (@Inc). Using seven key indicators, such as the rate of entrepreneurship and overall job creation, this list provides a comprehensive overview of fastest-growing startup-friendly cities in the U.S. The top three are Austin (#1), Salt Lake City (#2), and Raleigh (#3). There are many more you might not expect, and quite a few should be fantastic places to invest in the next few years.
Book I just finished and will reread soon (February 1, 2019)Awareness: The Perils and Opportunities of Reality. This short book has completely captured me. It was first recommended by Peter Mallouk, who said it gave him peace for weeks at a time. I grabbed the Kindle version with low expectations, devoured it in three days, and I’ve since bought 20 copies of the paperback to give out to friends [Update: 60+ copies]. It found me at the right time and won’t resonate with everyone, but it has equally impressed several of my best buddies.
What I’m reading (February 8, 2019) Germs in Your Gut Are Talking to Your Brain. Scientists Want to Know What They’re Saying (via @nytimes). Though microbiome science is still in the early stages, it’s fascinating to imagine the implications for Alzheimer’s disease, autism, and other conditions. Hat tip to reader Sam McRoberts (@Sams_Antics) for the recommendation. It’s worth the read.
What I’m reading (February 15, 2019) Excerpts from Where Mountains Roar: A Personal Report from the Sinai and Negev Deserts by Lesley Hazleton (@accidentaltheo). You can find the specific section that I’m (re)reading here: page 1 and page 2. I was given the excerpts by a tour guide while trekking through the Negev not long ago.
What I’m reading (March 1, 2019) How to Be Successful by Sam Altman (@sama), the president of Y Combinator and co-chairman of OpenAI. Here is one of the many paragraphs I highlighted in Evernote: “Most highly successful people have been really right about the future at least once at a time when people thought they were wrong. If not, they would have faced much more competition.”
What I’m reading (March 8, 2019) Reflecting on My Failure to Build a Billion-Dollar Company by Sahil Lavingia (@shl). This is the story of a wonderful philosophical reboot. Nearly everyone should consider reading it. Thanks to reader @lucasgabd from Rio de Janeiro for sharing with me via Twitter. For more great lessons from “failures,” check out “What I Learned Losing a Million Dollars.”
What I’m reading (March 15, 2019) Seeking the Productive Life: Some Details of My Personal Infrastructure by Stephen Wolfram. (Hat tip to the incredible Kevin Kelly for the recommendation.)
What I’m reading (March 22, 2019) Ten Lessons I Learned While Teaching Myself to Code by Clive Thompson, an outstanding author and long-form journalist. I particularly enjoyed his section on automation. Here’s a teaser: “‘Don’t learn to code, learn to automate,’ writes the coder Erik Dietrich. This is bang on. Nearly every white-collar job on the planet involves tons of work that can be done more efficiently if you know a bit of coding.”
What I’m reading (short) (April 5, 2019) From Bubble to Bubble by Sahil Lavingia. This is a wonderful article about moving from tech and hyper-liberal San Francisco to conservative-heavy Provo, Utah, and the lessons learned along the way. Sahil’s very humanizing perspective reflects a lot of reasons I moved from SF to Texas.
What I’m reading and listening to (April 12, 2019)The Moth Presents All These Wonders: True Stories About Facing the Unknown. Here’s the description: “Celebrating the 20th anniversary of storytelling phenomenon The Moth, 45 unforgettable true stories about risk, courage, and facing the unknown, drawn from the best ever told on their stages.” I’ve only read 50 or so pages, but one of my favorites thus far is Unusual Normality (YouTube option here if any loading issues) by Ishmael Beah (@ishmaelbeah). Reading one short (2–5-page) story over tea or coffee in the morning is a nice jumpstart to the day.
What I’m reading (May 17, 2019) The Art of Spirited Away by Hayao Miyazaki. Spirited Away—as mentioned in my chat with Adam Savage—is my favorite movie of all time. This book is awe-inspiring and shows the depth of world-creation that makes Miyazaki a legend.
What I’m reading (May 24, 2019)The Art of Memoir by Mary Karr. I’ve long been fascinated by Mary Karr (@marykarrlit), and I finally picked up her book on the craft of memoir writing after a recommendation by Michael Pollan. It applies to much of life, and I’d consider it a philosophical guide in many respects, replete with the dead serious (e.g., how to communicate past abuse) and spit-up-your-coffee funny (e.g., catshit sandwich metaphors). Highly recommended if you work with the written word in any capacity.
What I’m reading (very short) (June 14, 2019) Why I Am a Bad Correspondent by Neal Stephenson (@nealstephenson), one of my favorite sci-fi writers. This short, anti-comms blog post contains gems like this: “The quality of my e-mails and public speaking is, in my view, nowhere near that of my novels. So for me it comes down to the following choice: I can distribute material of bad-to-mediocre quality to a small number of people, or I can distribute material of higher quality to more people. But I can’t do both; the first one obliterates the second.”
What I’m reading and rereading (June 28, 2019) Consciousness Medicine: Indigenous Wisdom, Entheogens, and Expanded States of Consciousness for Healing and Growth by Françoise Bourzat. This book is brand-new, but I’m already on my second read. I’ve been waiting a year for it to be published! Françoise is one of the world’s foremost experts in navigating “expanded states of consciousness,” and she has ~30 years of experience combining indigenous training with modern tools. As Michael Pollan recently posted on Twitter, “Françoise Bourzat has written an authoritative book on guided psychedelic therapy with important lessons for anyone thinking of either guiding or being guided.” Ralph Metzner wrote the foreword, and endorsements on the back cover include pioneers like Gabor Maté, Ann Shulgin, James Fadiman, and Charles S. Grob, professor of psychiatry at the UCLA School of Medicine.
Here is a partial description from Amazon: “Françoise Bourzat—a counselor and experienced guide with sanctioned training in the Mazatec and other indigenous traditions—and healer Kristina Hunter introduce a holistic model focusing on the threefold process of preparation, journey, and integration. Drawing from more than thirty years of experience, Bourzat’s skillful and heartfelt approach presents the therapeutic application of expanded states, without divorcing them from their traditional contexts. Consciousness Medicine delivers a coherent map for navigating non-ordinary states of consciousness, offering an invaluable contribution to the field of healing and transformation.” Highly recommended for anyone interested in this work.
What I’m reading (July 26, 2019)The French Burglar Who Pulled Off His Generation’s Biggest Art Heist (New Yorker). After my previous mention of the Sour Grapes doc in 5BF, my brother, who’d also read Billionaire’s Vinegar, said, “Oh, if you like that, I have something you’ll really like.” He sent me this New Yorker piece.
What I’m reading (August 2, 2019)Deathwatch for the Amazon: Brazil has the power to save Earth’s greatest forest—or destroy it (Economist). This just came out yesterday, August 1st, and it is excellent. I’ll share another piece I’m reading on the same topic in the NYT, as the NYT doesn’t automatically require an account signup to read the full article.
Under Brazil’s Far-Right Leader, Amazon Protections Slashed and Forests Fall (New York Times). This is very important. How it is resolved, or not, will almost certainly affect the entire planet. Below are three excerpts to give you a flavor:
During a recent visit, Germany’s minister of economic cooperation and development, Gerd Müller, called protecting the Amazon a global imperative, especially given the rain forest’s vital role in absorbing and storing carbon dioxide, essential to the effort to slow global warming. And when trees are cut, burned or bulldozed, carbon dioxide goes directly back into the atmosphere.
“We’re facing the risk of runaway deforestation in the Amazon,” eight former environment ministers in Brazil wrote in a joint letter in May, arguing that Brazil needed to strengthen its environmental protection measures, not weaken them.
“Without tropical rain forests, there’s no solving the climate” issue, Mr. Müller said during an event in São Paulo.
What actions or countermeasures do you think might help mitigate this deforestation, whether by individuals (Brazilian, American, or otherwise) or the US administration? Please let me know on Twitter, using #planetarythreat, which will allow me to find your answers.
What I’m reading (August 30, 2019) The Glorious, Almost-Disconnected Boredom of My Walk in Japan by Craig Mod (@craigmod), from WIRED. I printed this out weeks ago and placed it on my kitchen table to read. Each time I walked past it, I had the distinct feeling of “this seems important for me to read,” and it was. This article is a beautiful and highly tactical description of long walks, using technology on your terms, and finding stillness. Here are two paragraphs out of many that I loved:
I have configured servers, written code, built web pages, helped design products used by millions of people. I am firmly in the camp that believes technology is generally bending the world in a positive direction. Yet, for me, Twitter foments neurosis, Facebook sadness, Google News a sense of foreboding. Instagram turns me covetous. All of them make me want to do it—whatever “it” may be—for the likes, the comments. I can’t help but feel that I am the worst version of myself, being performative on a very short, very depressing timeline. A timeline of seconds.
In the context of a walk like this, “boredom” is a goal, the antipode of mindless connectivity, constant stimulation, anger and dissatisfaction. I put “boredom” in quotes because the boredom I’m talking about fosters a heightened sense of presence. To be “bored” is to be free of distraction.
What I’m most excited about (and reading in the New York Times) (September 6, 2019) Johns Hopkins Medicine launches the world’s largest, and U.S.’s first, center for psychedelic research. This is something I’ve been working on for ~1.5 years and something diligent scientists have been working toward for 20+ years. I couldn’t be happier, and it wouldn’t have happened without generous support from Steven and Alexandra Cohen (@cohengive), Matt Mullenweg (@photomatt), Blake Mycoskie (@blakemycoskie), and Craig Nerenberg. Many thanks also to Benedict Carey of the NYT (@bencareynyt) for investigating and reporting on this from multiple perspectives, as he’s done for many years.
I shifted most of my focus from startups to this field in 2015, and it’s incredibly important to me that this watershed announcement helps to catalyze more studies, more ambitious centers, more scientists entering the field, and more philanthropists and sources of funding taking an interest in psychedelic science. There is much more reputational upside than reputational risk in supporting this work in 2019 and beyond.
Book I’m enjoying (September 6, 2019) Payoff: The Hidden Logic That Shapes Our Motivations by Dan Ariely (@danariely). So far, I’ve found this book to be very compelling and actionable. The real-world stories are heart wrenching and keep the pages turning. It’s a short read and might take 2–4 hours to finish.What I’m reading (September 27, 2019) Exhalation: Stories by Ted Chiang. I’ve previously recommended Ted’s incredible collection of short stories titled Stories of Your Life and Others. Despite the fact that Ted started off as a part-time science-fiction writer with a full-time technical writing job, he is the equivalent of Martin Scorsese or Wayne Gretzky in the sci-fi world—he has won four Hugo, four Nebula, and four Locus Awards, among others. The hit film Arrival (94% on Rotten Tomatoes), one of my favorite movies of the last 3–5 years, is based on one of Ted’s short stories. Gizmodo has written that “the arrival of a new piece of short fiction by Ted Chiang is always cause for celebration and parades and wild dancing.” Exhalation, his newest collection, may be even better than his last. It’s just so damn good.
What I’m reading (October 4, 2019) To Pay Attention, the Brain Uses Filters, Not a Spotlight.
What I’m reading and practicing (October 11, 2019) 50 ways to be ridiculously generous — and feel ridiculously good by Alexandra Franzen. This is a great list, which I found recommended on the website of fellow Austinite Professor Raj Raghunathan, author of If You’re So Smart, Why Aren’t You Happy?. If overwhelmed by options, try this: give an extra $10 or $20 to the barista next time you buy coffee. Give $5 of that to the barista and pay for the next person or next few people behind you. Simply walk out after the drive-by karma bomb. The afterglow is incredible and can last hours. Paradoxically, the fastest path to feeling better is often this type of indirect route, and it makes me think of this quote sometimes attributed to Henry David Thoreau: “Happiness is like a butterfly: the more you chase it, the more it will evade you, but if you notice the other things around you, it will gently come and sit on your shoulder.”
What I’m reading (October 18, 2019) Metformin and exercise — déjà vu all over again? by Dr. Peter Attia (@peterattiamd). This landed in my inbox on Sunday, courtesy of Peter’s weekly email newsletter. It explains why some of my friends who used to take metformin for longevity have stopped taking it. This short piece is also a great primer on thinking about extending healthspan versus lifespan.
What I’m reading (October 25, 2019) —Model hallucinations by Philip Gerrans and Chris Letheby (@chrisletheby) (Aeon). Thanks to Jason Silva (@JasonSilva) for bringing this to my attention. This entire piece is worth reading, but here are a few paragraphs that really jumped out at me:
How does this story explain the therapeutic effects of psychedelics? As we’ve seen, the self-model is an integrated bundle of predictions – and lots of these predictions, built up over a lifetime of experience, can make us deeply stressed and unhappy. A person with social anxiety expects and experiences the world to be hostile and uncontrollable because she feels vulnerable and unable to cope. The self-model that produces these feelings magnifies the adversity of her social world. Similarly, people with depression anticipate and recollect failure and unhappiness, and attribute it to their own inadequacy. Their self-model makes it hard to access positive experiences, and often feeds on itself in a negative downward spiral. Because our brains are endlessly trying to predict what’s next and reduce the likelihood of error, it’s no wonder that our expectations of ourselves tend to be self-fulfilling.
Theoretically we should be able to re-engineer the mechanisms of our self-model, and so change the way we organise and interpret our experience. The problem is that the self-model functions in a way that’s quite similar to the lenses of our eyes. We see with them and through them, but it’s almost impossible to see the lenses themselves, to really appreciate how they affect the signals that reach us, let alone take them off if they are unhelpful. In general, the mind presents us with the finished product in the form of images, not the modelling processes themselves. So too with the self: for better or worse, we feel like unified entities, not complicated and precarious hierarchical models that track and predict our organismic responses to what’s happening.
The second effect is more subtle. It concerns the way that psychedelics can enlighten us about the processes behind our own subjectivity. When the self falls apart and is subsequently rebuilt, the role of the self-model seems to become visible to its possessor. Yes, this offers a psychological reprieve – but more importantly, it draws attention to the difference between a world seen with and without the self. For an anxious or depressed person, psychedelics make it possible to appreciate the intermediate, representational role of the self-model. Ego dissolution offers vivid experiential proof, not only that things can be different, but that the self that conditions experience is just a heuristic, not an unchangeable, persisting thing.
What I’m reading (November 8, 2019)I Wrote This Book Because I Love You: Essays by Tim Kreider (timkreider.com). Many of you know that Tim’s We Learn Nothing, his dazzling collection of humor and insight, is one of the few books in the Tim Ferriss Book Club. To get a taste, you can listen to one of my favorite chapters, “Lazy: A Manifesto,” in this short 20-minute episode of the podcast. I’ve been eager to revisit Tim’s work, and I’m now digging into his latest collection of essays. Tim’s fans include people like filmmaker Judd Apatow (@JuddApatow), who gave him the blurb of all blurbs: “Tim Kreider’s writing is heartbreaking, brutal and hilarious—usually at the same time. He can do in a few pages what I need several hours of screen time and tens of millions to accomplish. And he does it better. Come to think of it, I’d rather not do a blurb. I am beginning to feel bad about myself.”
What I’m reading (November 15, 2019) The Keto Diet’s Most Controversial Champion in the Atlantic, by Sam Apple (@samuelapple). This is a nearly unbelievable, made-for-film story. The Atlantic’s Paul Bisceglio summarizes the basics well: “13 years ago, the chemist Patrick Arnold went to prison in baseball’s infamous BALCO steroids scandal. Today, he’s all in on keto—and his experiment collaborations could actually have big implications for medicine. Sam Apple (@samuelapple) delivers a wild ride.” This piece involves two past podcast guests, Dominic D’Agostino, PhD, and “rogue chemist” Patrick Arnold. It’s an unlikely but perfect pair. Huge credit to Dom for reaching outside of academia for ideas and solutions, and huge credit to Patrick, who has helped launch a massive wave of research and commercial interest. Their work and innovations could help change how we treat dozens of serious illnesses (cancer, Alzheimer’s disease, etc.).
What I’m reading (November 22, 2019)A Pickpocket’s Tale: The spectacular thefts of Apollo Robbins by Adam Green (@Adam___Green) (New Yorker). This was sent to me by Jeffrey Zurofsky (“JZ” from The 4-Hour Chef.) Here’s one paragraph to give you a taste:
When Robbins hits his stride, it starts to seem as if the only possible explanation is an ability to start and stop time. At the Rio, a man’s cell phone disappeared from his jacket and was replaced by a piece of fried chicken; the cigarettes from a pack in one man’s breast pocket materialized loose in the side pocket of another; a woman’s engagement ring vanished and reappeared attached to a key ring in her husband’s pants; a man’s driver’s license disappeared from his wallet and turned up inside a sealed bag of M&M’s in his wife’s purse.
What I’m reading (December 6, 2019) The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company by Bob Iger (@RobertIger). The negotiation stories with Steve Jobs alone make this book worth the read. Podcast with Bob coming soon.
What I’m reading (December 13, 2019)20 Podcast Predictions for 2020 from Top Industry Leaders by Steve Pratt (@steveprattca) of Pacific Content. This is a thought-provoking list of predictions for 2020, conveniently grouped into categories (advertising, new revenue models, consolidation, international opportunities, etc.). Contributors include many big platform, content, and media players. Hat tip to Courtney W. Holt (@mootron) for sharing this on Twitter. 2020 is going to be a very exciting year for podcasts…
What I’m reading (December 27, 2019) Every Amazon Shareholder Letter in a Single Downloadable PDF. Jeff Bezos (@jeffbezos) never ceases to amaze, and these letters really highlight how prescient and strategic he and Amazon have been since the 1990s. If you prefer a shortened version via audio, this is worth a shot and includes some fun trivia (e.g., What was the original name idea for Amazon.com? Click on this: Relentless.com…). Big hat tip to Ricardo of Most Recommended Books, whose site is also worth checking out.
What I’m reading (January 3, 2020) How Kepler Invented Science Fiction and Defended His Mother in a Witchcraft Trial While Revolutionizing Our Understanding of the Universe. Maria Popova (@brainpicker) is simply amazing. Her prose is worth reading for its beauty alone (keep in mind that English is not Maria’s native language!), and the stories in this essay highlight just how brilliant, stupid, ignorant, and insightful humans can be… sometimes all at the same time. [And that gets us caught up to today! Want to learn what I’m reading each week in 2020? Take 10 seconds and sign up for “5-Bullet Friday” here.Each Friday, you’ll get a super-short email, sending you into the weekend with fun and useful things to ponder and try.
Now, to all the Amazon books I purchased in 2019…]


I’ve added *** next to titles that made a strong impression; I’ve noted books purchased but unread; and I’ve added comments here and there. Any book already mentioned in 5-Bullet Friday has been omitted.
Are You My Type, Am I Yours?: Relationships Made Easy Through The Enneagram by Renee Baron and Elizabeth Wagele [Unread, but my curiosity was piqued about Enneagram after conversations with Tobi Lütke of Shopify and Drew Houston of Dropbox.]
The Gift by Hafiz, translated by Daniel Ladinsky***
Joyful Wisdom: Embracing Change and Finding Freedom by Yongey Mingyur Rinpoche, with Eric Swanson [Still unread but recommended by podcast guest Safi Bahcall.]
The Drama of the Gifted Child: The Search for the True Self by Alice Miller*** [Recommended by several podcast guests, including Dr. Gabor Maté.]
Let Your Life Speak: Listening for the Voice of Vocation by Parker J. Palmer [Still unread but highly recommended by Jerry Colonna.]
Maria Sabina: Selections (Poets for the Millennium) by Maria Sabina, edited by Jerome Rothenberg
A Sand County Almanac—and Sketches Here and There by Aldo Leopold, illustrated by Charles W. Schwartz
Fiend Folio: Tome of Creatures Malevolent and Benign: (Advanced Dungeons and Dragons) edited by Don Turnbull, illustrated by Chris Baker [As a kid, I was a bullied nerd who found refuge in D&D. This was a sentimental purchase to kindle memories of adventures as a chaotic-good gray elf.]
The Overstory by Richard Powers
The Courage to Be Disliked: The Japanese Phenomenon That Shows You How to Change Your Life and Achieve Real Happiness by Ichiro Kishimi and Fumitake Koga [Only half read so far, but I purchased it based on Marc Andreessen’s blurb on the Amazon page.]
The New One Minute Manager by Ken Blanchard, PhD, and Spencer Thompson, MD
The Things They Carried by Tim O’Brien***
High Output Management by Andrew S. Grove [Need to reread this one, as its lessons have faded.]
Backstage Cirque du Soleil by Veronique Vial (photographer)
From Third World to First: The Singapore Story by Lee Kuan Yew [Unread, but I saw this recommended by Patrick Collison, CEO of Stripe. It’s on my to-read list for 2020. If interested, my interview with Patrick on many topics can be found here.]
  • *
P.S. Want to see more? Sign up for “5-Bullet Friday,” and you’ll always be in the know. Each Friday, you’ll get a short email of five bullet points, sending you off to your weekend with fun and useful things to ponder and try. If you dislike it, it’s easy to unsubscribe. Easy peasy, lemon squeezy.
P.P.S. If you’re an avid reader, you might also enjoy the recent “Books I’ve Loved” series on the podcast. It has recommendations from heavyweights like Esther Perel, Seth Godin, and Steve Jurvetson. I also described some of my personal favorites in the series’ inaugural episode. Make sure to subscribe on Apple Podcasts, Spotify, or wherever you get your podcasts.

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