Global expansion
Want to enter the US market? Here’s how to pitch the big vision to VCs, talent and advisors
How to find your hook to get into the US and build your dream board of advisors.

It’s hard to fully appreciate the differences between the startup and venture capital ecosystems around the world until you’ve experienced them. It’s the people-watching, for lack of a better word, that reveals the most. What time people enter the office, whether a conversation happens in the open or behind closed doors, and the general bravado of founders. We were lucky to pick Bethany Crystal’s brains about this while she was in Australia.

Bethany is the VP of Portfolio Partnerships & Community at US-based executive talent marketplace Bolster. In her previous role as GM of Network at Union Square Ventures (USV), she worked with an impressive lineup of companies such as DuoLingo, Soundcloud, Coinbase, Jobbatical, Etsy and Foursquare to help empower their teams to learn from each other and build better businesses. Bethany’s first-hand accounts of how founders built these businesses has given her a unique insight on what exceptional leaders do differently, the value of building a bench of advisors and how to build a community — and not get caught up in the buzzword.

Watch the replay here, or read through the Q&A below.

You’ve worked with all the best founders and operators — what do they do differently, and what can we learn from them?

Here are 5 things that I’ve seen 5 CEOs do really well:

  1. Henry Ward, CEO of Carta. He is a prolific blogger. When they had to lay off people because of the pandemic, he posted a blog about it. When you read it, you can see his openness and that he’s not afraid to share his opinions, even when they’re dissonant.
  2. Brian Armstrong, CEO of Coinbase. Coinbase is always recruiting, particularly at the executive level. A couple of years ago, Brian wrote a piece on Medium about how they hire executives. It’s a 7-step process over several months. He talks about how it’s all about building relationships and seeing if candidates mesh with the team. Looking at where Coinbase is today, this is the recruitment process that got them there. Being intelligent and thoughtful about the hiring process is something I see in a lot of successful leaders.
  3. Luis von Ahn, CEO of Duolingo. Luis is great at telling Duolingo’s story. When he tells the story of how Duolingo emerged, people are literally sitting on the edge of their seats, as he describes it with so much passion and fervour. It doesn’t matter how many times he’s told it — it always sounds like this is the first time. It taught me how to embed that sort of passion into every single pitch that I do.
  4. Matthew Prince, CEO of Cloudflare. Matthew has this ruthless confidence that shines through in presentations and recruiting. The job of a CEO is not always that cut and dried. Having a person at the top of the leadership with gravitational pull made them successful. He’s led the company from the early days with his co-founders, all the way through to IPO, which is rare to see.
  5. Jeff Lawson, CEO at Twilio. He’s done a lot of great work writing about culture and team building. From his work at Twilio, you can see that they’ve looked inward and built a culture that people are proud of.

Many of these success stories that we do see, particularly in the US, are men. I hope to see more women at the top in the future.

Note from AirTree: Check out the Recommended reading & watching list at the bottom of this piece to see these examples brought to life.

Digging deeper into ‘confidence’, many Aussie and Kiwi founders find that tricky as we have more of a laid back culture. What’s your view on how to appear confident vs brash and arrogant?

There’s a phrase I recently got introduced to, which is “CEO Math”. And that is where you share accurate data, but round it up a little bit.

Many European-based founders want to present the full picture, including the bad stuff — and it’s good to be able to look at your business and see those things. But that’s not what investors want to hear all the time, and it’s not necessarily the image you want to be putting out.

The best founders have those honest conversations, but they’re happening with their investors either one-on-one or in smaller groups.

I think it’s important for founders to get out of their heads and paint the big picture, paint the big dream. Ask yourself audacious questions like “If we had $10 million or $100 million, what would we do?” Think about how you 10X or 20X your growth — you might have to knock it back a few notches, but dare to dream big.

What’s your advice for Aussie and Kiwi companies pitching to US-based VCs?

Just because a VC is US-based doesn’t necessarily mean that they’re going to make your dreams come true. They need to understand what your challenges are today, what your immediate goals are, and the networks and customer bases they can unlock for you.

Think about who you are talking to: what access do they have, and what can they bring outside of just capital?

At the end of the day, it’s about relationships. Don’t blindly email every partner at every firm. Pick one or two based on their previous investment history that would most likely be interested in your proposition. Start building those relationships up slowly, whether that’s through Twitter or online events.

For founders going over to the US, should they spend time there setting up their operations, or should they hire someone senior on the ground?

Every company has to find a hook to get into the US, and that hook will be different for everyone. Here are some examples I’ve seen at USV:

  • Funding Circle is a peer-to-peer lending marketplace that started in the UK. They wanted to expand to the US, so they set up an office in San Francisco and then doubled down from there. They divided their Executive team between those two locations and operated like two subsidiary companies under the same umbrella.
  • Clue is a menstrual health app based in Germany, but they’ve always been looking ahead. They’re getting a lot of traction because they got FDA approval to do fertility tracking. They brought a few people to Berlin from the US to help with content marketing, and that was helpful for them to get in the mindset of the persona before they had a physical presence there.
  • SoundCloud, the online audio distribution platform, looked at where they wanted to be geographically and find talent and customers before setting up offices in New York, LA and San Francisco. I think the best companies are intentional about moving people around and executives need to spend time in different offices. As soon as you start to splinter, keeping everyone on the same page can be challenging.

Location-wise, I encourage people to look beyond San Francisco. It seems like everything happens in the Bay Area, and that’s where you have to be. But it’s a really saturated market. I think USV has proven through their investments and presence on the East Coast that that’s not entirely true. You can get a better bang for your buck on the talent piece elsewhere. Now that more people are open to remote work, it doesn’t matter where HQ is located. You’ll get more diversity of talent in other locations too.

For Australian and Kiwi founders trying to hire US-based talent, what are some of the things that they care about?

The big thing is: What is the size of the opportunity here? How big could this be? How much could we win? There might be a misconception that if the company is starting in a smaller market, that limits how much it can scale up.

You need to pitch them the big vision. If you’re bringing on employees and paying them in equity, they’re going to want to know that this isn’t just something that will be popular in Australia and New Zealand; it can be a global product.

How should founders think about engaging advisors?

Building your bench of who you go to for advice is the best way to boost yourself as a CEO and company leader. Take the time to map out the things that are important to you and your business, and then look at those areas to see where you have gaps, and that’s where you want to bring in additional help.

There’s an idea that we see gaining popularity at Bolster that we’re calling surge staffing. It’s when founders don’t have the capacity to play two roles at once, but they don’t need a full-time hire. Go-to-market is a great example of this. You don’t need an entire team to always be working on US expansion, but you do need one or two people to double down on it in the first couple of months. Doing this at an executive level has other benefits, like giving your cofounding team exposure to great talent in different areas so that no one stays stagnant.

What’s your advice about how to pitch your company to attract these advisors?

Matt Blumberg, the CEO of Bolster, gave an example of where he got this wrong at his previous company Return Path. He came up with a bunch of people who he wanted to be advisors and gave them all a bit of equity and hoped they would return his calls. But he wasn’t really engaging and unblocking that group well. He burned a lot of equity in the business by giving it away for free.

Now he’s been more intentional at Bolster, formalising an advisory board. In addition to having these people provide help and advice, he carved out space for them to be angel investors in our next round, which meant they were feeling bought into the work we’re doing. Finding an incentive structure that’s aligned with what you want to achieve is important.

How would you start building relationships with potential advisors?

They say the best CEOs are always recruiting, and that isn’t just for their team. It’s also about your advisory network and mentors. It means when you get introduced to people, staying in touch with them. It means setting intentional goals for yourself to expand your network. You should treat building your network like you would if you’re managing a CRM of customers — you need to keep those relationships hot!

One thing that we’re thinking about a lot right now in the US is how do you expand the diversity of your network? Are you only meeting people who look like you and share your industry background? If you looked back on your external meetings from the last couple of months, would you be hitting your diversity goals? It’s quantifying your bias and figuring out who you are spending your time with, then intentionally seeking out relationships with new groups.

From my personal experience at USV, I used to take a lot of one-on-one introductory calls. Every time I had a conversation with someone, I would say to them, “Let me know how things go, and please follow up in 3–6 months.” Only a handful of people did over 5 years. If you’re the person that follows up, that gets noticed.

What are some of the cultural differences you’ve noticed since you’ve been in Australia around venture capital and startups?

There’s more of a work-life balance here in Australia. I’m working out of a co-working space, and often I’m the only one there. I know I’m working weird hours, but people aren’t there before nine or after six. That’s very different to New York City, where people work around the clock. It’s a lot healthier in Australia.

There’s also more of an international perspective here. In the US, there can be very myopic, siloed thinking that’s just US-focused. That’s problematic for founders when they want to go international and end up making stupid mistakes. When you’re thinking about international expansion, having humility and recognising that there are many different perspectives out there is a really good thing that Australians can bring to the table.

You’ve built engaged communities with many startup operators and teams — what are your tips for engaging with a community effectively?

Community has become a buzzword and catchall for a lot of things, which is problematic. Right now, everyone thinks they need a community. The fact is, it takes a long time to build a community. You can spend a lot of money, effort and time building a subpar community.

Many people assume that every event they run is a community event. A lot of the time, it’s just another panel event or discussion. If your goal is to educate, that’s one thing. But if your goal is to build community, you need engagement.

One of the things I loved about working with the companies in USV’s portfolio was that community was an inherent part to the products they were building. Some communities that I’ve seen created with intention — not for the sake of it — are:

  • DroneBase runs an operator network of drone pilots worldwide that fly drones and share their footage. They’ve cultivated a community from that network, and it’s been helpful for them to have people to talk to, share tips and best practices.
  • Figure 1 is a medical photo and information sharing app with a community of healthcare professionals they work with. Their app is like an Instagram for healthcare workers where doctors are sharing images and getting feedback from other doctors. To drive more engagement on the platform, they’ve found ambassadors at local colleges and med schools.

What are the key mistakes you’ve seen founders make?

For me, one that’s top of mind is not saying goodbye to things fast enough — whether that’s people or ideas.

When you go to the next level of your business, you’re not always going to bring everyone with you. And sometimes you have to say goodbye. I’ve heard many CEOs reflect on not saying goodbye to people soon enough. They feel bad doing it, but the team around them feel even worse about having a person bringing them down.

I’ve worked in companies where we pursue something for so long that it blinds us to other options that exist. You always need to pull up, look around and see if anything has changed. It can be tempting to want everything you start to succeed and force things to fit when they’re not always right.

How do those conversations play out when a business has outgrown a person?

This is why I think talent fluidity and on-demand work is important. There’s a perception that you join a company, give it your all for 4 or 5 years until you burn out, and then go to another company and do the same thing again. That’s fine because people want their full equity vesting. But the problem is that that timeframe doesn’t work for everyone, and you start to get diminishing returns as people get stuck in their heads and are less productive.

We should all stay above board and have the hard and scary conversations like, “I want to learn something that you can’t teach me,” or “We’re doing something that’s beyond your skillset.” Have honest conversations about business and human needs. If you have someone whose role has outgrown them, but they’re passionate, and you want them to stay in the business, find them a mentor or get them functional coaching to help fill in the gaps. At the end of the day, people want to be successful in the jobs that they’re doing.

Recommended reading & watching

How to Build Your Board — ebook by Bolster
A better offer letter — a popular piece Henry Ward from Carta ran about how to better educate employees on startup equity
Draw the Owl and Other Company Values You Didn’t Know You Should Have — Jeff Lawson on culture and values at Twilio
The story behind Duolingo’s mission — presented by Luis Von Ahn
Matthew Prince’s Twitter — to get a sense of his confidence

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