The 9 Best Investors to Follow – Soak Up The Wisdom

Investing is not just about chasing the money.

It’s about understanding where the smart money is going and why.

By tuning into the decisions of the most successful investors, you can get a feel for emerging trends, potential growth areas, and even some pitfalls to avoid. If you’re curious about which way the wind’s blowing, here are nine top investors to keep an eye on in 2023.

And I promise none of them is Warren Buffett.

Best Investors to Follow In 2023 – Overview:

  1. Reid Hoffman
  2. Naval Ravikant
  3. Travis Jamison
  4. Chris Sacca
  5. Fred Wilson
  6. Jessica Livingston
  7. Tim Draper
  8. Bill Ackman
  9. Benjamin Graham

Reid Hoffman

Reid Hoffman might ring a bell for many as the co-founder of LinkedIn, but his impact extends far beyond just one platform.

After LinkedIn’s success, Hoffman transitioned into the world of venture capital, becoming a partner at Greylock Partners. His knack for spotting potential in early-stage startups is noteworthy. As a fund manager, he’s backed companies like Airbnb, Dropbox, and Facebook during their nascent stages.

Beyond just writing checks and growth investing, Hoffman is known for his mentorship, often sharing his insights on scaling businesses and building strong company cultures.

His podcast, “Masters of Scale,” dives deep into these topics, offering listeners a chance to learn from various industry leaders. In the vast sea of investors, Hoffman stands out not just for his successful bets, but for his genuine commitment to fostering innovation and guiding the next generation of entrepreneurs.

Check out his content here:

Naval Ravikant

Naval Ravikant is one of those names that’s become synonymous with startup wisdom and insightful investing.

He co-founded AngelList, a platform that revolutionized how startups raise money and how job seekers find positions in these budding companies. But Naval’s influence isn’t limited to just AngelList.

Over the years, he’s made personal investments in over 100 companies, including big names like Twitter, Uber, and Yammer. What sets Naval apart isn’t just his keen eye for promising startups, but also his philosophical approach to life and business. He’s a frequent source of bite-sized wisdom on Twitter, touching on everything from wealth creation to mindfulness.

For those in the startup world, Naval is often seen as a guiding light, not just for his investment prowess, but for his thoughtful reflections on building a meaningful life in the midst of business chaos.

Check out his content here:

Travis Jamison

Travis Jamison isn’t your typical investor; he’s a blend of entrepreneur and investor, seamlessly transitioning between the two roles based on the opportunities that arise.

Starting out as a “serial entrepreneur,” Travis founded roughly a dozen small businesses, all bootstrapped. His entrepreneurial spirit didn’t stop there. He later delved into the investment world, bringing with him a unique perspective to investing. His investing philosophy has been shaped by his hands-on experience in building businesses from the ground up.

Among his ventures, he’s known for his involvement with Smash Digital, an SEO-focused company, and, a platform dedicated to investment insights. Travis’s approach to investing is informed by his entrepreneurial journey, making him a valuable resource for startups and fellow investors alike.

Whether it’s SEO, digital assets, or the broader investment landscape, Travis’s insights are a blend of practical experience and forward-thinking strategy.

Check out his content here:

Chris Sacca

Chris Sacca is a bit of a legend in the investment world, especially if you’re into early-stage startups.

Before he became a household name on shows like “Shark Tank,” Chris was busy making some incredibly savvy investments through his venture fund, Lowercase Capital. We’re talking early bets on companies like Twitter, Instagram, and Uber.

But it’s not just his track record in growth investing that makes Chris stand out.

He’s got this down-to-earth, cowboy-shirt-wearing persona that’s pretty refreshing in the often buttoned-up world of venture capital. Beyond the world of tech, Chris is vocal about social issues and is known to champion causes he believes in.

For budding entrepreneurs and investors alike, following Chris is a bit like getting a masterclass in spotting potential and understanding the startup ecosystem, all while keeping things real and grounded.

Check out his content here:

Fred Wilson

Fred Wilson is one of those steady forces in the financial world, consistently making waves without a lot of unnecessary fanfare.

As a co-founder of Union Square Ventures, Fred’s had a hand in funding some of the internet’s most influential companies, including Twitter, Tumblr, and Etsy.

But if you’re thinking he’s just another face in the high-rise world of VC, think again. Fred’s been sharing his thoughts on startups, investing, and the tech industry at large through his blog, “AVC,” long before blogging was the “in” thing to do. It’s this transparency and willingness to share insights that make him a favorite among entrepreneurs.

While Fred is one of the greatest investors out there, he’s no Warren Buffett. He’s not just about the numbers; he genuinely cares about the tech community and its potential to bring about positive change.

For anyone looking to understand the nuances of venture capital and the ever-evolving tech landscape, Fred’s insights are a goldmine.

Check out his content here:

Jessica Livingston

Jessica Livingston might not always be in the glaring spotlight with other successful investors, but her influence in the startup world is undeniable.

As a co-founder of Y Combinator (YC), one of the most renowned startup accelerators globally, Jessica has been instrumental in shaping the early stages of companies like Dropbox, Airbnb, and Stripe. But it’s not just her role at YC that makes her noteworthy.

Jessica has a genuine, nurturing approach to startups, often emphasizing the human side of building a business. She’s been a vocal advocate for founder well-being, diversity in tech, and the importance of company culture. Which arguably has contributed to her successful investing career.

Her book, “Founders at Work,” offers a candid look into the early days of some now-giant tech companies, providing invaluable lessons for budding entrepreneurs.

In a world where the startup narrative can often be dominated by valuations and exits, Jessica’s perspective is a refreshing reminder of the passion, grit, and human stories behind every venture.

Check out her content here:

Tim Draper

Tim Draper is a bit of a maverick in the investment scene, and that’s saying something given the characters in this space.

Founder of Draper Associates and DFJ, Tim’s been in the game long enough to see tech booms, busts, and everything in between. His portfolio? Oh, just a few names you might recognize: Skype, Tesla, and Baidu.

But Tim isn’t your typical sit-back-and-watch kind of investor.

What makes him one of the greatest investors are his bold predictions, like his unwavering belief in cryptocurrencies way before Bitcoin became a household name. And if you’ve ever heard him speak, you’ll know he’s got this infectious enthusiasm about the future of tech and its potential to reshape societies.

While he’s made headlines for his investments and predictions, at his core, Tim is a passionate advocate for innovation and the entrepreneurs driving it.

For those looking to get a pulse on where the future might be headed, with a side of spirited optimism, Tim’s your guy.

Check out his content here:

Bill Ackman

Bill Ackman, with his sharp suits and even sharper investment strategies, is one of the most famous investors who’s ever hit the financial markets.

At the helm of Pershing Square Capital Management, Bill’s made a name for himself not just for his big bets, but for his activist approach to investing. He doesn’t just passively invest in the stock market and follow broad brush economic trends.

No, he’s known to roll up his sleeves, dive deep into company operations, and push for changes he believes will boost shareholder value.

A sort of antithesis to Warren Buffett.

His investments span a range of industries, from fast food chains like Chipotle to pharmaceutical giants like Valeant. But it’s not all just numbers and boardroom battles for Bill. He’s been candid about his investment missteps, offering a rare glimpse into the highs and lows of the hedge fund world.

For those keen on understanding the intricacies of activist investing, and getting a dose of the human side of high-stakes finance, Bill Ackman’s journey offers a wealth of insights.

Check out his content here:

Benjamin Graham

Benjamin Graham is objectively one of the most successful investors in history. Often dubbed the “father of value investing,” his is a name that resonates deeply within the investment community.

His legacy as a value investor isn’t just about stock market success or the wealth he amassed.

It’s more about the foundational investment philosophy he developed and shared. In his book “The Intelligent Investor,” Graham emphasized the importance of analyzing the intrinsic value of companies. He advocates for a disciplined approach that differentiates between investing and mere speculation.

His principles, which stress the significance of a margin of safety and the role of Mr. Market, have stood the test of time, influencing generations of investors.

One of the world’s greatest investors, Warren Buffett, often credits Graham’s teachings as the cornerstone of his own investment strategy.

Beyond his writings, Graham’s tenure as a professor at Columbia Business School left an indelible mark, shaping the minds of many who ventured into the world of finance. In a realm often swayed by trends and emotions, Graham’s rational, methodical approach remains a beacon for those seeking long-term investment success.

Check out his content here:

Bonus – Up and Coming Investors to Keep An Eye On

As a reminder that even the greatest investors of all time had to start from somewhere, here are some up-and-coming investors you might want to keep an eye on.

Amy Cheetham from Costanoa

Key Deals: Flexio, Highline, Highnote, Kevala, Malga

Background: Before joining Costanoa in 2019, Amy ran North American sales strategy and operations at Zuora, a public enterprise software company. She also spent three years investing in growth-stage technology companies at Summit Partners.

Nicholas Chirls from Notation

Key Deals: Bison Trails, Circle, Parsec, Stellar Health, Talos

Background: Nicholas has been a fixture in the New York City tech ecosystem since 2009. He co-founded Notation in 2015 and focuses on inception-stage investing in product-focused founders based in New York City.

Elad Gil from Gil Capital

Key Deals: Airbnb, Airtable, Coinbase, Deel, Figma

Background: Elad is the co-founder and chairman at Color Genomics. He has been an operating executive and investor or advisor to private companies such as Airbnb, Airtable, Coinbase, and many others.

How We Chose the Investors for This List

Selecting the investors for this list wasn’t just about their financial acumen or the returns on their investments. While success in the market is undoubtedly a factor, we delved deeper, looking for individuals who offer more than just impressive portfolios.

Here’s a breakdown of our criteria:

Diverse Investment Philosophies

We wanted a mix. From value investing stalwarts like Benjamin Graham to modern-day mavericks like Travis Jamison, this list represents a range of investment strategies and philosophies.

Inspirational Journeys

Some of the investors, like Jessica Livingston and Reid Hoffman, have taken unconventional paths to success, proving that there’s no one-size-fits-all approach to the world of investing.

Educational Value

Investors like Fred Wilson and Naval Ravikant consistently share their insights, offering budding investors and entrepreneurs valuable lessons. Their willingness to educate sets them apart.

Impact Beyond Investing

Many on this list, such as Bill Ackman and Chris Sacca, have made significant contributions outside of their investment portfolios, be it through philanthropy, activism, or mentorship.

Unique Personal Stories

Every investor on this list has a backstory that’s both intriguing and inspiring. Whether it’s overcoming adversity, challenging the status quo, or simply following their passion against all odds, their personal narratives add a layer of depth to their professional achievements.

Influence on Future Generations

The likes of Benjamin Graham, and thus Warren Buffett, have left legacies that continue to shape the investment world, demonstrating the lasting impact of their philosophies and teachings.

Adaptability and Innovation

The investment world is ever-evolving, and many on this list, such as Tim Draper with his early belief in cryptocurrencies, have showcased an ability to adapt, innovate, and stay ahead of the curve.

In essence, this list is a blend of past legends and present-day trailblazers, each bringing a unique perspective and value to the world of investing. It’s not just about the numbers; it’s about the stories, the lessons, and the inspiration they provide.

Your Turn

In the big world of investing, it’s cool to see people who are more than just good with money. They have great stories and give us hope.

From old-time legends to today’s stars, each one shows that being successful is about more than just making smart money moves. It’s about who you are and the choices you make. As we think about our own money goals, it’s nice to have these inspiring folks to look up to. Also, remember to check these blogs from venture capitalists.

They remind us that investing is not just about dollars and cents, but about dreams and journeys.


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