Q&A with Raffaele Riva, London and New York-Based Angel Investor

Raffaele Riva

Splitting his time between London and New York, Raffaele Riva boasts an impressive and diverse career spanning startup missions, from conception to fruition and most recently as an angel investor in the field. With a strong portfolio citing over a dozen early-stage company investments across a ten-year career, Riva has managed to stand out in a relatively new scene, making strides in the angel community and helping bourgeoning entrepreneurs get innovative ideas off the ground.

A British national, Raffaele Riva completed multiple degrees in and around London before earning an MBA from Saïd Business School at the University of Oxford – an experience Riva credits for his first taste of entrepreneurship, starting a small tech firm in 2006 alongside colleagues with whom he’d studied. Riva saw his first business grow capital quickly and immediately connected with the funding elements necessary in new startups. After the team grew and sold the business, Riva turned his sights toward investment opportunities and developed his passion as an angel, working closely with CEOs and business owners to realize company potential. Hard work, sleepless nights and a bit of luck proved Riva’s knack for keen investments, and ten years later, Raffaele Riva has made a name for himself amongst New York’s growing angel scene. His authority as a thought leader in the field has led to recognition from a number of esteemed NYC outlets as he’s participated in dozens of webinars, conferences and public events around the country.

As an angel investor, Raffaele Riva has worked the last decade helping to fund early-stage companies, financing dedicated founders with bright ideas in exchange for a piece of the growth potential possible in successful investments. Riva’s vast experience provides both financial and intellectual capital as his entrepreneurial acumen lends a unique perspective of advice and guidance to new startups as they grow.

Walk our readers through a typical morning routine for you.

Seven days a week I wake up before sunrise, walk to my favorite coffee shop about a block down, check my emails and start the workday. I’m operating with various CEOs and businesses across the globe, so 5am in New York is 10am in London and my teams across the pond have already had their first meetings of the day and set new agendas, so an early start is required in order to keep the day moving for all parties involved. I usually work from my home office for the first few hours of the day – setting priorities and retracking the days’ tasks; and around 7am the whole household is up and running. My wife will usually get our two daughters ready for school each morning, and I like having this bit of time with our hectic little family every day for 20-30 minutes before we’re all out the door for the day around 7:30am. On weekdays my schedule doesn’t stray too much from the norm – still up around 5, coffee, work, then we find some free time for lunch and activities with the girls.

What is a healthy habit you keep that enhances your productivity?

I have found that taking time out for personal gains has always kept my mind and body aligned for success in business. Taking a bit of time out every day for a quick run or for meditation will always be more productive than letting myself feel consumed with work or over-stressed from meeting agendas or to-do lists. I credit daily meditation practice to part of my successes, both personal and in business! I always recommend Dan Harris’ 10% Happier written about five years ago – I really connected with his message and have since studied meditation techniques. I can’t speak highly enough of how meditation and intentional deceleration have impacted my life. I think that the healthy habit here is finding what works for you, whatever that may be, owing yourself a moment each day to stop, reflect and reign in the chaos of the outside world.

If you could give advice to your younger self, what would it be?

In that same theme, I would absolutely tell young Raffaele to slow it down! I have been on a constant race for 15 years – and don’t get me wrong, I think I’m the luckiest guy in the world to get to do what I do, helping others build on their goals – but I worried a lot when first starting out. I would tell myself that no matter the outcome, my hard work will eventually pay off. That advice would likely help me let go of a lot of the stress that came with our early startup environment.

Additionally, I would surely advise any young angel investor to remember that the founder is always more important than the big idea. We’ve seen big ideas come and go. We’ve seen a lot of money put into mediocre people with great ideas; but at the end of the day, the business is about the people involved. There are various ways to value a company, but first and foremost we must invest in people who are willing and able to put in the real work.

How do you stay organized throughout the day and complete the tasks you need to complete?

I’m a meticulous planner and I have a great team around me who helps me stay on schedule. I’ve always told my partners and CEOs – if you can’t write down your tasks or meticulously manage a calendar, hire someone who will! Having an administrative assistant is often necessary for these “big picture” folks, and it’s a crucial part of my team as well.

What drove you to bring your investment dreams to life?

From the moment I’ve started pursuing investments in new businesses, I’ve had the chance to help others make their dream a reality – this is what drives me every single day. I remember back to my first startup, and the lessons learned from early investors were invaluable. On top of that, I have fun working alongside new teams, and hopefully at the end of a project yield a return – win/win. With a solid portfolio, angels really can get a strong financial return while reaping so many other benefits, like helping to launch intelligent, fulfilling companies in their communities; meeting entrepreneurs who drive new ideas; and working with friends who make me a smarter investor pushing for lucrative opportunities. We hear it all the time in the angel community: do good, learn something, have fun and make money…not particularly in that order. If you seek out founders and investments that speak to you and to your values, it will always be a learning experience.

What is a piece of advice you would give to someone coming to you for investment in their startup?

It’s critical for entrepreneurs to figure out what kind of capital fits their vision for their company – this is my first question when approached for investment. Equity capital from an angel investor is only right for some companies and some visions. We tend to look for companies that plan to scale really quickly and want hands-on involvement from their investors, and these startup plans should set out to grow and exit at high value to ensure a high return for all involved. I encourage founders to really get to know the process of investment – look for resources online and talk to other startups – and figure out a five-year plan for their business. We often turn down ideas that we don’t feel will align with these values.

What is an obstacle you’ve experienced in your work and how did you work through it?

As an angel investor, we know that every new investment comes as a major risk – it’s just part of the business. The biggest obstacle has been finding that sweet spot in learning the what/where/how/why to invest. Even when investing in the best companies and the brightest ideas, literally half of these businesses are going to fail, but the challenge comes in making smart, sound decisions with the intention of having a solid portfolio regardless of failures. If I can continue to build a portfolio, ideally a couple of businesses yield a return, and even more optimistically, a few others will give massive returns – say, 30-40x the investment. At the end of the day that balance is what keeps us all able to continue putting money into bright ideas and energetic people.

What is a financial idea you’ve been brainstorming that you can share with our readers?

I’ve been really interested in the evolution of digital currencies for years now, but we’re just starting to see how they could really hold the potential to change the global economy for the better. This is no longer the libertarian pipedream, but we’re actually seeing this in practice hold universal value – especially in developing countries. In places like Venezuela, crypto adoption is remaining really strong amid the worst political chaos the country has seen in decades. By allowing digital currencies to bypass world markets, new generations are starting to become empowered financially. It’s all still relatively new, but there are a handful of startups using blockchain technology to fight poverty and promote health, human rights and social justice – many of them right here in the US. I don’t have a big idea in the space but I’m following these various projects in different stages of development and am amazed by the ideas being promoted and the social implications they may hold. The idea here is to encourage others to take notice.

I guess the same kind of volatility inherent in the risk of crypto is also what drives me to seek out smart investments. The possibility of high risk/high reward has always been my driving factor, and if at the end of the day the reward can encompass monetary gains and social good – we should all be looking for these wins.

Is there a software or web service that you use as an organization tool?

We use Gust religiously to network inside the entirety of the startup ecosystem. Tens of thousands of founders use the platform to list business information and organize smart investments, while angels can use the service alternatively to connect with entrepreneurs and manage investment programs – from application through evaluation.

What’s a book you would recommend to our readers?

Kiyosaki’s Rich/Poor opened my eyes in a lot of ways as a young adult taking the first steps in business school – classic canon for anyone considering making smart investments.

Daniel Kahneman’s Thinking, Fast and Slow took a turn from the usual numbers approach to investment themes and applied a deeper psychology to the processes. Kahneman really helped me think through my own subconscious biases and apply these toward business decisions. There’s something so methodical about his writing, and I’ve since been really interested in how our psychology makeup plays a part in finding successful investments. An insightful and interesting read, no matter your chosen profession!

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