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SuperAngel #189: Joe Cross, ex-operator Angel on thesis development, building networks and adding value

SuperAngel #189: Joe Cross, ex-operator Angel on thesis development, building networks and adding value

Learn how Joe Cross seeks out investments that embody the convergence of goodness, bigness, and speed and how it works as a compass that guides his path through the vibrant world of investing.

Today, we've got the pleasure of introducing Joe Cross, a visionary early-stage angel investor whose portfolio boasts an impressive roster of approximately 25 game-changing companies. This dynamic individual is not just your average investor; he's a tastemaker in the world of startups, with a knack for identifying ventures that have the potential to create a profound ripple effect on a global scale.

But Joe doesn't just stop at writing checks; he dives headfirst into the trenches alongside founders, offering his invaluable expertise in navigating the treacherous waters of growth and marketing across an eclectic range of industries.

In this ever-changing landscape, Joe Cross seeks out investments that embody the convergence of goodness, bigness, and speed. It's a recipe for success and a compass that guides his path through the vibrant world of entrepreneurship.

Before earning his wings as an investor, Joe honed his skills as the 12th employee of the groundbreaking company (Transfer)Wise. From 2012 to 2020, he donned multiple hats in the realms of marketing and growth, leaving an indelible mark on the company's trajectory. It's safe to say that Joe has an uncanny ability to spot opportunities and guide businesses toward unparalleled success. Today, we're thrilled to have him with us.

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Joe’s Journey Into Angel Investing

Back in 2007, Joe Cross embarked on a journey into the realm of internet marketing for companies. Little did he know that in 2012, his path would intersect with the nascent entity known as TransferWise. Joining the company as its 12th employee, Joe found himself at the forefront of an exhilarating early-stage adventure, fueling his passion for the fast-paced startup world.

Those years at TransferWise (today known as Wise) were undeniably some of the most exhilarating moments of Joe's life. The allure of the early-stage ecosystem had become an insatiable craving, beckoning him towards his present endeavors. After dedicating himself to the company for a remarkable eight-year stretch, witnessing and contributing to its growth and scale, Joe bid his farewell in 2020. But like so many of the best angels out there, his hunger for intellectual stimulation remained unyielding, despite his operator days being behind him.

Transitioning into angel investing was not a meticulously crafted master plan; it was more of an organic progression. Joe sought a respite from the frenetic pace of his previous endeavors, while still yearning to keep his mind sharp and engaged. Investing presented itself as the perfect outlet to bridge the gap seamlessly.

Moreover, Joe found himself in the privileged situation of having a couldn't chorus of venture capitalists and industry peers, eagerly inviting him to join them in their investments. The recognition of his strategic acumen led to invitations such as serving as an Expert in Residence for Seedcamp, an opportunity too enticing to pass up.

Seedcamp asked me to be an Expert in Residence and I was like: “Well, I can't say no to this!”

These were the kind of opportunities one could postpone indefinitely, but Joe's intuition propelled him forward. A few months into his new venture, Joe discovered an unexpected and genuine fondness for angel investing. It was a revelation that affirmed his path and solidified his commitment.

And so, there he stands today, driven by a passion for startups, armed with his experience and a hunger to make an impact in the ever-evolving landscape of entrepreneurship.

Joe’s Investment Thesis & Strategy

Joe Cross is a self-proclaimed impact investor, but he doesn’t draw hard lines in the sand. His approach is all about making a positive impact, but he doesn't adhere religiously to any particular ideology. Instead, he keeps it simple with three fundamental words: good, big, and fast.

First and foremost, Joe focuses on the "good" factor. He asks himself if the world truly needs what's on the table. Will it be a genuine step forward, benefiting billions of users? Surprisingly, answering this question often comes easy. Sometimes, disruption is necessary, exposing broken systems that the world would be better off without. Sure, there are winners and losers in the face of disruptive technologies, but on balance, Joe evaluates whether the greater good is served.

Next, Joe considers the "big" factor, looking at scale. Is it a consumer product with the potential to reach a billion users? Or perhaps a horizontal B2B offering that can penetrate vast markets? Scale matters, and Joe knows it.

But what truly sets his pulse racing is the "fast" element. He's come to realize that execution speed is the fuel that propels world-class ideas into the stratosphere. It's the secret sauce of a venture-worthy startup.

The sense of urgency radiating from the founder often connects back to the problem they're solving. And when the world needs that problem solved urgently, it's a powerful motivator.

Once those three boxes are checked, Joe gives the green light and dives deeper into the opportunity at hand.

In this ever-changing landscape, Joe Cross seeks out investments that embody the convergence of goodness, bigness, and speed. It's a recipe for success and a compass that guides his path through the vibrant world of entrepreneurship.

Joe’s Core Learnings from Angel Investing

Alright, we've got some cool insights to unpack here. Let's dive into Joe's perspective on investing, networking, and adapting to the ever-changing startup landscape.

First off, Joe emphasizes that he has had a shift in mentality when making investment decisions. It's not just about putting money into a company in any given industry; now Joe is much more disciplined in evaluating if the company aligns with his investment thesis and has the ability to execute on it. That's the key differentiator. Understanding this distinction is crucial in his approach.

Moving on, Joe acknowledges the wide range of expectations and needs that founders have when it comes to angel investors. It's not always about grand strategic questions.

Sometimes, it's the practical matters that matter most, like finding the right person for a job. From hiring to connecting potential customers, the value Joe brings extends beyond strategic workshops.

Joe is surprised at how valuable these recommendations can be and underlines the importance of appreciating and building your network constantly.

But Joe's had another important learning: As an ex-operator, he realizes the need to shift away from relying solely on the past experiences of companies like TransferWise. Sure, he could spend hours regaling tales of what they did at TransferWise, but that doesn't guarantee success elsewhere. Instead, Joe embraces the challenge of truly engaging with the specific context and sector at hand. It's about understanding what will work in the given circumstances.

Gathering insights from founders and aligning his thinking accordingly becomes a crucial part of the equation. It's about being proactive and digging deep to find the strategies and approaches that will yield success in the present, not just resting on laurels of past triumphs.

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Q: What is the most counterintuitive thing you've learned since you started Angel Investing?

Being a venture capitalist is no walk in the park, and I must admit, I underestimated the challenges involved. When I observed other investors, like those at TransferWise, it seemed like a glamorous life filled with travel and though of course still filled with hard work. However, I failed to grasp the true extent of the hard work until I experienced it firsthand.

The reality is that being a VC is both demanding and stressful. Managing someone else's money, especially when making pre-seed bets, adds a whole new level of pressure. It's a weighty responsibility that can't be taken lightly.

While using my own funds may not induce as much stress, navigating the waters of fund management is a different story altogether. Making investment decisions with someone else's money is a challenging task that can teach you just how difficult it truly is. It's not all smooth sailing and easy wins, contrary to what I may have believed in the past.

But despite the hardships, there is fulfillment to be found. Discovering promising startups, empowering talented entrepreneurs, and potentially making a lasting impact on the world is what keeps me going. It's an exhilarating journey, even when faced with setbacks.

So yes, being a VC is far from a glamorous ride. It requires resilience, dedication, and a willingness to endure the ups and downs. But let me tell you, the rewards, both personal and professional, make it all worthwhile.

Q: What would be your top tip to Angel's wanting to do more international investments?

The best approach, in my opinion, is to seek out the truly exceptional funds in a specific geographical region and establish connections with them. Instead of traveling to multiple countries and meeting countless founders right off the bat, it's more effective to gain a solid understanding of the markets through early-stage funds that have already established themselves.

It's about establishing a solid network and developing a deep understanding of the landscape.

So, rather than spreading yourself too thin, focus on finding and connecting with the top-tier funds in your target geography. Let them guide you on your journey, as they possess the wisdom and experience to navigate the intricacies of the market. It's a more strategic and effective way to learn and grow in the world of venture capital.

Q: What advice would you give a ten year younger self if you only had 30 seconds?

Sometimes, it's essential to take a step back and let go of unnecessary worries. We tend to overthink things, like avoiding difficult conversations or putting too much pressure on ourselves. But you know what? We don't need to carry that weight.

Just chill out, stop worrying about stuff I used to worry too much about.

Instead, embrace the challenging situations. It may take time to build resilience and feel comfortable in different environments. But the truth is, we often find that things work out just fine when we simply chill out and go with the flow. So let's not fret too much. Everything will fall into place. Trust me, it'll be alright.

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