Legendary investor Andy Rachleff shares invaluable lessons on personal and professional growth through curiosity, non-consensus thinking, writing, and decision-making. He advises on career advancement, leadership, learning from success and failure, and balancing passion with practical experience.

#19: Legendary investor Andy Rachleff joins Chris to chat about how you should be investing your money to build your wealth. They discuss the investing mistakes so many make, when it makes sense to pick stocks and why you might not want to max out your 401k.Andy Rachleff (@arachleff) is the co-founder and CEO of Wealthfront. He also serves as a the chairman of the endowment investment committee for University of Pennsylvania and as a member of the faculty at Stanford Graduate School of Business. Previously, Andy co-founded Benchmark Capital, one of the most successful venture capital firms of all time.Full show notes available at: https://allthehacks.com/investing-andy-rachleff Partner DealsFor all the deals, discounts and promo codes from our partners, go to: allthehacks.com/dealsResources MentionedGet $5k Managed for free at WealthfrontConnect with Andy: Twitter | LinkedInWealthfront: Website | Blog | Guide to Financial HealthWhy Angel Investors Don’t Make Money: TechCrunch ArticleWhy Rental Properties Are Not Good Investments: Wealthfront ArticleBurt Malkiel's Book: A Random Walk Down Wall Street Full Show Notes(00:32) Who Is Andy Rachleff? (Episode Overview)(01:58) Andy's First Investment(05:54) Andy's Path from Investment Banking to Venture Capital(08:39) How Great Companies Are Started(10:50) Why Did Andy Feel the Need to Start Wealthfront?(14:36) Can You Be Successful Picking Stocks?(19:48) Is an Angel Investment in a Startup a Good Investment?(21:42) How Can You Make Passive Investing More Exciting?(23:17) What About Investing in Alternatives Like Art?(24:09) Is Real Estate or a Rental Property a Good Investment?(27:19) Investing Hacks to Save Money on Taxes(33:39) How to Make Changes to Your Investment Portfolio(34:56) Does It Make Sense to Invest When Markets Are at All-Time Highs?(39:02) When Should You Speculate with Your Investments?(40:46) Don't Always Evaluate Your Investment Decisions by How Much You Made or Lost(41:38) How Should You Change Your Investing Strategy When You Have More Money?(42:40) Are Wealth Managers Worth Their Fee?(45:01) Why a Good Tax Advisor Is Better Than a Wealth Manager(46:10) Andy's Winning Tactics for Negotiating(48:35) Why You Should Always Be Pareto Optimal(50:06) The Value of Liquidity and Why You Might Not Want to Max Out Your 401(k)(55:24) How to Connect with Andy Rachleff Connect with All the HacksAll the Hacks: Newsletter | Website | Membership | EmailChris Hutchins: Twitter | Instagram | Website | LinkedInEditor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

The Co-founder of Benchmark Capital & Wealthfront explains the most important goal of a startup: how do you find product-market fit? As the man who coined the term, he’s the expert—and in this episode, he also shares lessons learned from legendary startup super performers such as Scott Cook, Reed Hastings, Don Valentine, and many others. Check out the new Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's new book Pattern Breakers is available now wherever you buy books.

Wealthfront Chairman and Co-Founder Andy Rachleff joins Jason for an incredible interview! They start the show by discussing the SVB situation before breaking down different tech mini-crashes throughout Silicon Valley history (2:28). Then, they break down Wealthfront’s business and how to know if a business has market pull (40:49). They finish up the show by covering a range of topics, from AI to stock-based comp (1:13:45). (0:00) Jason kicks off the show (2:28) SVB situation (9:26) The FDIC’s $250K limit (13:27) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups (14:49) The bank run (16:17) The SVB ecosystem (22:20) Merge - Integrate up to 5 customers for free today at https://merge.dev/twist (23:45) Cycle changes (36:15) How to judge a VC (39:27) Issuu - Get 50% off when you go to https://issuu.com/podcast and use promo code twist (40:49) Wealthfront’s operation (48:58) Reactions to the market (55:00) Modern analysis and stock buybacks (1:01:24 ) Caring about profitability (1:02:06) Attaining market pull (1:13:45) Andy’s thoughts on AI (1:16:31) The makeup of a great entrepreneur (1:18:50) Stock-based compensation (1:25:06) How we avoided inflation FOLLOW Andy: https://twitter.com/arachleff FOLLOW Jason: https://linktr.ee/calacanis

"If the customer doesn't scream, you don't have product-market fit." — Andy RachleffWelcome to another episode of The Tim Ferriss Show. This time, we have a slightly different episode—a takeover by Mike Maples, Jr.Mike Maples, Jr. (@m2jr) and his firm, Floodgate, have invested in and supported many of the startups you might recognize — including Twitter, Twitch, Lyft, Chegg, and Okta, among others — long before they were household names. He's been on the Forbes Midas List eight times in the last decade, but he's much more than a successful investor. Mike has also succeeded as both a founder and operating executive.He's also simply a great guy and the first person who really taught me how to angel invest. For more on that background, listen to my interview with Mike at tim.blog/mikemaples.In this episode, however, Mike speaks with Andy Rachleff (@arachleff), co-founder of Wealthfront and Benchmark Capital, about two of the biggest questions that should be on every start-up founder's mind: How do you reach "product-market fit" (a term that Andy coined), and how do they know when you've achieved it?Andy has known many of the start-up world's giants and synthesized their lessons, so you will also hear what Andy learned from Don Valentine of Sequoia, Scott Cook of Intuit, Reed Hastings of Netflix, Geoffrey Moore, Clay Christensen, Eric Ries, and Steve Blank.The audio from this conversation is from the premiere episode of Mike's brand-new podcast, Starting Greatness, which I encourage you check out. There are some incredible guests coming.So, if you like this conversation between Mike and Andy, be sure to subscribe to Starting Greatness on Apple Podcasts, Spotify, Overcast, or wherever you get your podcasts. You can also check out the website at greatness.floodgate.com, and on Twitter you can follow Mike at @m2jr and Andy at @arachleff.Please enjoy!This podcast is brought to you by Peloton, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I’ve been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. No worrying about fitting classes into your busy schedule or making it to a studio with a crazy commute.New classes are added every day, and this includes options led by elite NYC instructors in your own living room. You can even live stream studio classes taught by the world’s best instructors, or find your favorite class on demand.Peloton is offering listeners to this show a special offer: Enter the code you heard during the Peloton ad of this episode at checkout to receive $100 off accessories with your Peloton bike purchase. This is a great way to get in your workouts, or an incredible gift. That’s onepeloton.com and enter the code you heard during the Peloton ad of this episode to receive $100 off accessories with your Peloton bike purchase.This podcast is also brought to you by 99designs, the global creative platform that makes it easy for designers and clients to work together to create designs they love. Its creative process has become the go-to solution for businesses, agencies, and individuals, and I have used it for years to help with display advertising and illustrations and to rapid prototype the cover for The Tao of Seneca. Whether your business needs a logo, website design, business card, or anything you can imagine, check out 99designs.You can work with multiple designers at once to get a bunch of different ideas, or hire the perfect designer for your project based based on their style and industry specialization. It's simple to review concepts and leave feedback so you'll end up with a design that you're happy with. Click this link (99designs.com/tim) and get $20 off plus a $99 upgrade.***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests.For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Please fill out the form at tim.blog/sponsor.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The IO podcast with Sterling and Tyler features Andy Rachleff, the founder of Benchmark Capital and unicorn startup Wealthfront, and explores the intersection between investing and operating. Ratcliffe believes that finding product-market fit and being ambidextrous in finding new opportunities while optimizing existing ones is more important than being paranoid in either role. He also discusses the importance of learning from success and putting entrepreneurs first. Venture capitalist Bill Gurley emphasizes the importance of product market fit and finding an inflection point in technology to identify a non-consensus market that is desperate for a product. Rachleff admires investors Howard Marks, John Dora, and John Valentine, and considers Reed Hastings as an exemplary operator who makes asymmetric bets. The success of running a company or making investments is determined by the magnitude of success when you are right, and great CEOs must be like venture capitalists in adding businesses to their portfolio and betting the company through major development initiatives and acquisitions with a high chance of failure.Timestamps[00:00:00] Interview with Investor Operator Andy Rachleff[00:01:40] Investing vs. Operating Skills[00:03:32] Product Market Fit and the Art of Being Ambidextrous[00:05:41] From VC to Entrepreneur: How Wealthfront Was Born[00:09:41] Making Money & Taking Leaps of Faith in Non-Consensus Ventures[00:12:37] The History and Success of Benchmark's Equal Partnership Model[00:16:41] Insight on Product Market Fit with Andy Keen[00:19:03] Spotting Inflection Points: Technology Entrepreneurship and Venture Capitalism[00:20:22] Product Market Fit and the Thesis of Everything Going Wrong[00:22:51] Key Trait of Successful Entrepreneurs: Deep Understanding of Technology[00:27:07] Finding Desperate Customers for Startup Success[00:28:41] Why Great CEOs Layer New Businesses to Succeed[00:33:04] Best Startup for Asymmetric Bets Today?

Andy Rachleff, CEO of Wealthfront and co-founder of Benchmark Capital, shares insights on venture capital investing and entrepreneurship. He discusses the value hypothesis, growth hypothesis, and the mission of Wealthfront. The conversation also covers strategies for business success, product evolution, and the shift towards active management in investments.

Check out Wealthfront: https://www.wealthfront.com FOLLOW Andy: https://twitter.com/arachleff FOLLOW Jason: https://linktr.ee/calacanis

Andy Rachleff, Wealthfront's co-founder, discusses transitioning from investor to entrepreneur, emphasizing authentic opportunities over constant correctness. He explores the power of organic growth, inflection points in entrepreneurship, and data-driven personal finance advice.

Venture capitalist Andy Rachleff discusses traits of successful entrepreneurs, product-market fit, building Wealthfront, hiring strategies, day trading vs index investing, tax-loss harvesting, and thoughts on bitcoin.