What European Founders Get Wrong Before Expanding to the US | Stephan Dietrich (Neolane, Adobe) | part 2

5 Aug 2026 · 42 min · 16 chapters

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In short

Part 2 of a conversation with Stephan Dietrich on what European founders get wrong before expanding to the US, focusing on the investor/VC side and “readiness” for US growth.

Guest backgrounds

Stephan Dietrich is an experienced entrepreneur who expanded to the US and later became an investor. He invests in US expansion (Lead Edge Capital) and has direct SaaS investments (33) and board roles (6). He previously had an exit/integration experience at Adobe.

Key claims

Don’t half-ass the US; it’s not a satellite office and costs and complexity are higher. Biggest gap is talent: hiring, incentivizing, retaining, and “peeling the onion” to verify real capability. European products often need simplification for US use cases; many European entrants face existing US competitors. Founders often wait too long to enter; go earlier even at ~$2–3M traction if strategy is clear. Also, commit enough capital—underfunding leads to hiring weaker talent and underbuilding go-to-market.

Notable examples

BlaBlaCar as an exception concept; marketing tech in 2007 (few vendors) vs today (thousands). Dietrich’s Adobe integration example: synergy models took time; reps only adopted acquired products after proving success in specific accounts.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Stefan's Journey from Entrepreneur to Investor

0:45 to 2:30

Stefan discusses transitioning from being an entrepreneur to becoming an investor.

“If you haven't caught part one, it's basically Stefan's entrepreneurial journey to the U.S.”

Guiding Principles as an Investor

2:30 to 5:40

Stefan shares his investment philosophy and the principles guiding his decisions.

“that wasn't compatible with my health condition anymore.”

The Importance of Team and Coachability

5:40 to 7:40

Stefan emphasizes the need for a coachable team when investing.

“So focusing on that, becoming an investor and saying, hey, here is my guiding principles.”

Adjusting to the Investor Role

7:40 to 10:00

Stefan reflects on the adjustments he had to make as an investor compared to being an entrepreneur.

“It's how my own investment philosophy works.”

Evaluating Founders and Market Readiness

10:00 to 12:00

Stefan discusses how he evaluates founders and their products for US expansion.

“And the fact that you go from one baby deeply into like a portfolio strategy all of a sudden.”

Challenges of European Products in the US

12:00 to 14:00

Stefan talks about common challenges European products face when entering the US market.

“So more in what we call the growth stage of the business.”

Understanding U.S. Market Challenges

14:00 to 19:29

Learn about the key challenges European founders face when entering the U.S. market.

“has its own product, has its own leaders, has a lot of backing already, has a lot of like financing.”

Timing and Market Entry Strategy

19:30 to 22:22

Discover the importance of timing and having a clear strategy for U.S. expansion.

“Uncle Sam doesn't always have a good reputation and some team members are going to be like, oh, you know, again, it's one of the US.”

Talent Acquisition and Management in the U.S.

22:23 to 27:01

Understand the critical role of talent acquisition and management in U.S. expansion.

“and I'm like, Frank Sinatra's song is in my head.”

Financial Commitment and Expectations

27:02 to 28:00

Gain insights into the financial commitments required for success in the U.S. market.

“And is there anything else that you've learned being an investor that you've done since being an operator?”
Show all 16 chapters

Understanding Market Costs in the US

28:00 to 29:23

Learn about the significant cost differences for marketing and events in the US versus Europe.

“So when you look at the full package, it's not that different, but just the perspective of it looks like the optics of it look so much higher than people are sometimes.”

Insights from Acquisition Experiences

29:23 to 30:25

Stefan shares lessons learned from his acquisition by Adobe and how it affects deal flow.

“It's the cost of doing business in the US.”

Creating Synergies Post-Acquisition

30:25 to 33:58

Explore how to create successful synergies and leverage post-acquisition dynamics.

“One of the three or several of the three things is like, hey, do I have more product coverage?”

Evaluating Founders for Investment

33:58 to 36:59

Understand the criteria for assessing founders and their potential for successful exits.

“And as an investor, Stefan, how do you think about the founder?”

The Evolution of Founders and Companies

36:59 to 39:24

Discuss the phases founders go through as their companies evolve and the need for new leadership.

“And one is additive to the other, by the way.”

Advice for European Founders

39:24 to 40:09

Stefan emphasizes the importance of taking risks and seizing opportunities in the US market.

“people look at you, they look up to you saying, hey, you've been there, you've done it.”
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Transcript

Automatic transcript. May contain errors.

0:11Hi, everyone.

0:12Matt Oxley:David Rose here from USXP. Welcome back to the Scaling Stateside podcast, along with my co-host and co-founder, Matt Oxley. We are on a mission to help founders from the UK and Europe better understand the US expansion journey. We are having part two of our discussion with Stefan Dietrich from Lead Edge Capital. He kind of covers both realms of the companies we talked to. So he's also an experienced entrepreneur who's expanded to the U.S. And now he is an investor who funds U.S. expansion for entrepreneurs coming to the U.S. So this is part two of our conversation. If you haven't caught part one, it's basically Stefan's entrepreneurial journey to the U.S.

0:50Matt Oxley:If you haven't caught it, there's some great tidbits in there. Be sure and check that out. Today, we're going to talk about the other side of the table, which is the venture capital fundraising side. So with that, Stefan, welcome back. Great to talk with you again. Thanks for making time to speak with us. Hey, thanks, David. Thanks, Matt. Glad to be back again. Well, if I may, Stefan, because I think one of the really interesting components of your story is making that leap from operator, founder, call it what you may, into an investor and into being a VC in the kind of mindset shift that maybe had to go on on that journey, on that step.

1:31Would you mind just unpacking that a little bit for us? Yeah. Yes, that's quite a difference to be on the other side of the table. And it requires, I think, a lot of humility to get there. Because when you're an entrepreneur, you're 100 % focused on one baby. You have one baby, that's your business. Very often you have one concentration of wealth too. You have all your wealth is in there, your concentration of efforts, sweat equity and pure equity is in there. So you're maniacally focused on one company. So the first adjustment you have to go through as soon as you start investing your own money and you consider this to be the new chapter in your life, which I considered after having also a health issue.

2:19So the health issue was the trigger for me to really stop operating and go into another type of dynamic, I think, also and another type of stress level also that wasn't compatible with my health condition anymore. So I knew I had to make a change. So that was like a compelling reason to do it. I would have started other companies. It's not the ideas that are missing here. but it's just like felt it's the right thing for me. Also, you know, I've been married for 30 years. We're celebrating 30 years. My wife has seen me build three businesses with my co-founders, the same co-founders. She's seen me grinding three times and she said, you know, the fourth time, the fourth one is not going to be with me.

3:09Because you're insane. You're insane when you're in that mode because it's day and night, right? It's all of a sudden, it's like you give birth to a new baby. I mean, it's like day and night. So the compelling thing was like health and then a family decision saying, you know, this is don't restart from scratch, right? I'm not going to be supporting you in like these early days of grinding. Even if like financially, you have more comfortable and everything. If you're passionate about something, it becomes a little crazy. So the fourth one is going to be without me. So that felt was like, that's a pretty good reason.

3:41also to switch to an investor model. So it's not just the decision of choice. It was also driven by external factors. That's what just I want to illustrate. So now all of a sudden you're sitting on the other side of the table and you have to make a few decisions. First, you want to create like a VC fund that has LPs, that is borrowing money from someone, commitments and redistributing them into like portfolio companies and being some sort of a marketplace between supply and demand. and match that. And my decision was clearly, no, I am not willing to start a fund. I had tons of offers to like, you know, from other people saying, hey, you have great track record, let's start a fund, a projection fund together, like specializing on Europe to US expansion.

4:27I think that's a very good idea out there to say, hey, I'm going to bring a lot of resources to bear. And my fund is going to be specializing in that. So that was one of the ideas. But no, I wanted to invest in the same spirits as I wanted to build businesses, is build them for the long run. Which means like invest forever, potentially. So invest my own money and invest it in a way that feels like you don't have to exit after four, five, six years. You don't have the pressure of LPs to return the money because some businesses are just amazing or some businesses take longer. So having that pressure, I didn't want to have that pressure.

5:06So you have to have some sort of guiding principles also as soon as you get to the other side of the table and become an investor. And among my guiding principles were like, okay, I want full freedom. Because actually what's magical when you have an exit and you make money is all of a sudden it allows you to spend time on what money cannot buy. You know, freedom of investing wherever you want, freedom of time of investing, health, privacy, things like that are things that you cannot buy or you cannot really buy much. So focusing on that, becoming an investor and saying, hey, here is my guiding principles.

5:49I want to invest forever, potentially. So it's going to be evergreen. I don't have the pressure to report my decisions, for example. to explain my decisions to LPs, to raise money, to be able to, you know, survive in a fund, to have an expiration date on each investment, right? Because they physically have an expiration date. You have to create DPI if you want to raise the next fund so you're under pressure of time. So establish these guiding principles. For me, it was like freedom of investing wherever I want. You also have limitations when you're in a fund, right? So it's like, Like, oh, I cannot do defense.

6:30I cannot do like some certain types of gambling or things like that. So that's the first thing to establish the framework of your investments philosophy. Then the heuristics, of course, of your investment, you know, what are the type of companies you go after. So I have like a framework of eight criterias that I like to look at. So it's more growth stage, et cetera. So there's a bunch of financial things, but there's those things like, hey, the coachability of the team, you know, So for me, it's critical. You have great teams, but they don't need any help. But that's not a good fit for me. I was about to double down on that because I think you then have that alternative operator experience you're bringing into investment.

7:15Would you say that the way that you were looking at the founders was your differential when you're obviously investing in a portfolio company? Was that something that you were, you know the value add you were taking to the founders that you were you were looking to invest in yeah one of the critical component in my investment heuristics is is the team in looking for help are they open and looking for help and that's different from like pure vc funds who want to cut checks and move to the next one because i have that entrepreneurial background and what i want to bring to the table is smart money right that's as me personally i'm not speaking with a lead edge hat or with a BC hat, etc.

7:57It's how my own investment philosophy works. I want to bring smart money. So I want to work with teams I feel comfortable with, products I understand, and a team, a leadership team that's open and willing to get some help, some external help and recognizes their limitations. So they're amazing founders. They don't want any help, but it's not a great fit for me. So once then you make that decision, you found the investments, then yes, it takes a lot of humility to sit on the bench. You're sitting on the bench, like it's soccer time, right? I hope you watched the French soccer game last night. Congratulations.

8:39You're sitting on the bench and you're watching the other players play. You're not on the field playing anymore. And that is really a lot of adjustment. That is so much adjustment because all of a sudden, you're like, don't do that pass. It's going nowhere. I know this is going nowhere. I've done it. I have scars on my back. So you have to have the humility to say, hey, here is what I suggest. Here is what you should consider when you make that decision to go that partnership route, to develop that additional product, to do this. And I've seen them, like I've seen so many where I was like, I don't think it's a great idea to develop that new product range because it's another buyer.

9:21So are we going to be able and credible to sell to another buyer in the organization? And the team is like, hey, we're still going to commit 5 million. Thanks for, you know, thanks, no thanks. And it's like, okay, I'm going to disagree and commit, right? I'm going to support you in that and we're going to try to make the best of it. You are on the field. You are the players doing the passes on the field. You're playing. I'm not. I'm just a supporting character. I'm like on the bench trying to coach you, trying to tell you, you know, what is my experience? What would I do in this situation? And you make the decision.

9:55So I make suggestions, you make decisions. So that's a lot of adjustments. And the fact that you go from one baby deeply into like a portfolio strategy all of a sudden. You have like five, 10, I have 33 now, 33 SaaS businesses I invested directly in. So six I'm on the board of. And so it becomes more of a portfolio strategy, even if I don't see it that way. But the real VCs are in a pure portfolio strategy. You know, when something goes south, they just don't give a shit. It's pretty sad, but I've seen a few of those going on right now because they're going to make it up on some others. But when you're a founder, you're attached to your babies.

10:36You want to love your child equally. You know, all your childs, you love them equally, et cetera. and you want to go deep into every of these situations, but you can't because there's too many.

10:47Matt Oxley:I know as a long-time operator, of course, I think there's a tremendous advantage to investors who've also been operators. Some of the topics you were just talking about, but you have that experience of not only being an operator, but an operator who has expanded already to the US, right? Successfully. How does that lens of that experience, how does that help you or how does that influence your process when you're talking to founders and they're talking about coming to the US. How do you think about that experiences and how do you help coach founders and how do you evaluate potential new deal flow when you're talking about coming to the US based on those experiences you've had previously?

11:25Yeah, there's a lot there, right? It's like, hey, you use your own experience, but then you also draw from a lot of data that you acquired over the years and pattern recognition in terms of readiness, I guess, right? It's like, hey, is this team, is this organization, is this product, is this go-to market potentially ready to go to the US? Can we replicate some of the success they've had in their domestic markets? I only look at businesses that are above 10 million in annual recurring revenue. So more in what we call the growth stage of the business. So they've had product market fits in their local domestic markets in Europe or in a couple of markets in Europe.

12:11But they've also had go-to-market fits in these regions, right? And I differentiate the two, product market fit and go-to-market fit. So they have that traction in their domestic markets. And now can we replicate that in the US? So product readiness is, of course, one of the things. very often I think funders are too the European products are usually very good. They're usually on par if not better than American products. And they're holding back too much on that very often. Very often the products are too complicated. The UI is too sophisticated. Because in Europe very often the markets are smaller so you need to go deeper.

12:57You need to make it more sophisticated because you need to answer to more use cases because the companies are asking you this, this, this, kind of add this feature, etc. So it turns into something that's a little too sophisticated. And in the US, it's a little bit more cookie cutter. So you need to simplify the UI, you need to adapt the product. So product readiness and how you're going to adapt the UI and a product to US use cases is definitely a key a key thing. And I'm very obsessed by product. It all starts with product, right? The innovation of the product, but also the differentiation of the market.

13:30How is this going to be different than the current competitor? Generally speaking, 100 % of the businesses I've seen emerge in Europe, when they expand in the US, they already have competitors. I've never seen, except with some exceptions, a real unique new concept out of Europe that goes into the US. One exception, you know, BlaBlaCar, for example, you know, the ride-sharing company in Europe. They never made it to the U.S., but that's clearly a concept that doesn't exist in the U.S. But generally speaking, the U.S. has its own product, has its own leaders, has a lot of backing already, has a lot of like financing.

14:11You're not the first one in the U.S. So looking at the product is a key piece. organizational readiness. You know, is there the will and the skill of that organization to tackle major challenge like the US? Who is willing to go there from the founders? You know, who is willing to commit from the founding team or from a leadership team to bring the culture, to bring the knowledge, to bring everything that is not that easy to describe, and the experience, the customer stories. Also, a number of these customer stories never relates to the U.S. logos. Sometimes they do in some specific verticals. They recognize the names, et cetera, but it's difficult.

14:59So having that ability to understand the organization, you know, in some European countries, the ability to do everything in English all of a sudden. It sounds obvious, but it's not that easy. There's some organization I've met that are only speaking French. They're only speaking German in their board meetings with their investors, with their employees. All the internal communications are done in the local native language. So is that organization going to be ready to go to the U.S.? Are these founders willing and open to change that? And all of a sudden to standardize on English and adopt culturally also a lot of the standards?

15:43It's not a, you know, something to... Not trivial.

15:46Matt Oxley:Definitely not trivial. Not trivial. No, no. And you can see founders telling you, I want to do the US, et cetera. As soon as you say, okay, who's going? Is your wife fine? Is your family fine to go? Have you had the conversation with your leadership team, with your founders, co-founders? Oh, no, but we'll hire a local guy who's going to be the head of the US. I'm like, okay, that's a red flag. Okay, it's absolutely good. So things like that. Lessons learned, you know, access to capital, ability to commit big amounts of money in a country where everything is more expensive. Very often they say, you know, hey, I want to go to New York City.

16:29I'm like, okay, great. Why New York City? Give me three good reasons to go to New York City or Silicon Valley. Okay, give me three good reasons. Oh, you know, it's where everybody is. Okay, it's not a good reason. Okay, it's where blah, blah, blah. You know, it's a fun city. It's cosmopolitan. It's huge. We can find a great talent pool. It's great. Yeah, you're going to find a great talent pool, but you're like a drop in the ocean compared to like Google, Facebook, Amazon, whatever hiring there and all your local competitors, you know. So I'm going to have a hard time to attract, retain, pay, talent.

17:06So, oh, my wife only goes if I go to New York City. Okay, that's a good reason. That's going to be a good reason.

17:13Matt Oxley:You just need to know that you're embarking a structure, a cost structure that's probably 30 % to 50 % more expensive than if you were going to Nashville, if you don't have a clear reason to go to New York City. Oh, I only sell to ad agencies, or I only sell to finance at Wall Street. Okay, that's a good reason to be in Manhattan. So there is so much to assess there. In terms of readiness to go to the U.S., financial capital commitments, how much are you going to raise? How much do you commit? Then you have a lot of founders that are like, hey, I think we can make it with like 5 million. It's like, yeah, we did it with 5 million a while ago, back in the New England days in 2007.

18:00You can't do it with 5 million anymore. I'm sorry. The times have changed. The salaries have increased. The competition is fierce to get talent. and accessing that talent is the most difficult piece for you. So what's your angle to access the talent? What's the story you're going to tell someone? Back to the story we were sharing on like, you know, it's like hiring a sales rep in France to sell Portuguese wine in the Burgundy region. You know, it's like, it's not an easy, it's not an easy sell when you go home and see your wife or your significant other, say, by the way, I'm going to quit my job and go for that Portuguese wine companies to sell wine in Burgundy.

18:38So there's just a lot to unpack that I learned over the years in raising enough money, being committed enough. And I think it was in your question also, don't half-ass it, right? You cannot half-ass the US. The US is not a satellite office. The US is going to break every bone of your body personally and it's going to break every organizational bone you have. Just be ready on the roadmap, on the internal comms, on the processes, on the financial side, because it's going to be so expensive, on the culture of your organization that we'll have to adapt. And in some European countries, France included, you have some anti-Americanism, you know.

19:31Uncle Sam doesn't always have a good reputation and some team members are going to be like, oh, you know, again, it's one of the US. Oh, the US is asking for that in the roadmap. Oh, they're giving us a hard time. Oh, we hate the Americans, blah, blah, blah. Why this, what that? So you're going to have to be ready. You have to be ready as a founder to nip that in the bud, saying, no, this is our commitment. We're going there. We're committing financially, organizationally, from a product standpoint, et cetera, et cetera. So you cannot half-ass it. This is not just the distribution office. This is something that's going to influence all aspects of your business.

20:09I love it. It's so in line with the conversations that we have with founders. And I think they fall into a number of camps. One is they are over familiar with the US markets. Therefore, they're taking it for granted and therefore they're not prepared because we watch the same TV shows and read the same kind of news content. or they're fully underprepared. You know, they're almost scared of taking the leap. It's the fear that comes from, you know, going out there and putting yourself on the line. And what is the one thing you would recommend any founder listening to this about to embark, no matter what camp they're in, that they should be thinking about?

20:55What's that one bit of advice you would give? Yeah, very often I'm asked, you know, what's the biggest mistake we've done going there? And I've thought a lot about that. And I think the thing is we were too late. We were just too late. So we went when we were like 15 million on track to do 15 million. We should have gone earlier because the market was getting structured. it was as a reminder it was in the marketing tech space in 2007 so there were only like a bunch of vendors in the marketing tech space maybe like 20-30 when we entered the US market today there is 9 ,000 according to like some different landscapes from analysts so we waited too long and if you have something innovative, if you think you have like a vision and something differentiated Even at 2, 3 million, you can go, right?

21:57If you are able to show that you're going to have a clear strategy, very laser-focused strategy of how to succeed in the U.S., the differentiation you can have with your product, with your go-to market, et cetera. So you don't wait too long. Don't wait for so long. Don't hold yourself back. And we were holding back. When I landed there, I remember I landed in New York, JFK, took the flights, and I'm like, Frank Sinatra's song is in my head. When I landed, I remember very vividly when I landed in New York City, and you drive from JFK into the city and you see all of a sudden the skyline. And I landed in New York because we hadn't yet decided that we're going to go with Boston as a secondary city.

22:42So, and I knew New York, and I see the skyline, and I have the song of Frank Sinatra in my mind saying, if you can make it there, you can make it anywhere. So all of a sudden you have that huge commitment that you're taking. And it's like, hey, retrospectively, we waited for too long. We should have gone earlier. We could have raised more money. We could have built a bigger business. And the reality is our number one competitor sold at$2 billion. They raised more money, way more capital, $140 million in the last round. Our last round was$28 million and it was considered big already. and we're just holding back.

23:19We're all holding back too much. It's like when you play tennis, right? Don't hold back these like shots. Just like go for it. Like, you know, go big or go home, but don't do it in a stupid way either. I'm not a high growth, high burner type of guy. I'm very disciplined in terms of like spending the resources because we raised only like a total of like 35 million to get to an exit to see like 600 million. So it was very disciplined. And we only burned like 20 million total. So you, but yet you have to commit. You have to commit early and the earlier the better. So that's my advice. Don't wait too long.

24:02Matt Oxley:So you've obviously seen this story, this US Expansion story from both sides of the table, right? So you've obviously done it as an operator and you've seen it from the investor side quite a bit. And you've touched on this a couple of different points, but if you were going to say, what is the one biggest gap that founders from Europe need to understand before they come? We've touched on talent, we've touched on capital and location. What is the one thing you need to really understand really, really well before you take that leap? What would you say that is? One thing is really talent. I think talent in our space, right?

24:37In tech, again, I'm talking from a perspective of like tech, software, that's my experience. B2B SaaS software technology, where accessing the right talent is day and night. And having the angle, the story, the ability to do backdoor checks, for example, on talent, which is so hard, you know. Is this person really good? You know, we talked about the onion and the multiple layers of the onion, right? All the onions look the same. They look beautiful. Some are rotten inside. Some are empty and dried out inside. Some others are just amazing. So you have to be able to peel off all these layers of the onion to see, you know, is this person a high quality person to drive our U.S.

25:23growth, our U.S. expansion? And that's the hardest when you show up in a country that is so culturally different from a business standpoint. Also, they assume, we assume we talk the same language. So getting access to the right talents, attracting the talents, incentivizing the talent, knowing how to incentivize them, retain them is really hard. It's the one thing I think is the hardest. Sorry, David. And do you see that from now being, playing for the other side? Is that the thing that you're picking up on? You're seeing all of these portfolio companies through potentially, you know, making those mistakes.

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26:08That's something that you've now observed. And as an investor, you're able to point out. Is that how you come to that? Yes. I see it day in and day out. I was like, oh, you know, I just took a board. The first reaction is like, hey, we know this guy in the US. He can be our head of US. Okay, great. Okay, tell me more. Yeah, you know, we've interacted with him. It looks good. He has a great tag record. He made quota. He made quota every year. He made President's Club every year, etc. I was like, I've never met someone who hasn't.

26:43Matt Oxley:How does everyone you interview the top salesperson in the company? That's amazing. Oh, it's amazing. That's the US. The beauty of the US storytelling. They're all the best. So yeah, so I see it day in and day out. And I think it's, you know, hire, hire, tough, manage, easy is applicable here even more. And is there anything else that you've learned being an investor that you've done since being an operator? We've obviously got talent. Is there anything else that you've learned that you've observed? Yeah, I think half-assing it on the financing side. Very often the teams think they can get there with not as much money as they thought.

27:30So by half-arsing, you mean not getting enough capital? Yeah. Not committing enough capital. Like they want to hire someone and you hear it's like, oh my God, this is like 400K, 200 plus 200 to have a head of US or 450 or 500. And people in Europe is like, these are big numbers. And by the way, it's a little unfair because you don't have all the social charges in addition. It was like the company charges, the company taxes and fees and the social fees and everything. So when you look at the full package, it's not that different, but just the perspective of it looks like the optics of it look so much higher than people are sometimes.

28:12Oh no, we're going to just hire a lower profile. You know, we're just going to settle with someone who's not as strong. And so that's always like a big cultural gap. So, and everything also the campaigns, You do a webinar or you do an event. You run an event in New York City to grab an in-person event. You do a dinner with a bunch of prospects or customers or you do an event in a venue, etc. You want to do a user conference in the U.S. to gather your user locally, etc. and build momentum with that. Everything is very expensive. And a lot of these companies need help in just saying, no, no, I think this is market standard.

28:53Your webinar is going to cost you 25K, and not 5K like in Europe. You want to have a conversation with an analyst like Gardner and Forrester. Yes, it's going to take you a seat. It's going to be 50K a year. I was like, what? To do what? So like, okay, to have the right to talk to them and get access to research. So that's where I think we can help with our experience. Saying, no, this is market standard. This is the way it is. It's the cost of doing business in the US. But then the deals that you can sign And the value you can extract with your product, with your service can be so much higher too.

29:32So you need to be able to understand these differences. And I think we have a responsibility there in helping these teams navigate these differences.

29:43Matt Oxley:How do you, Stefan, since you had gone through the exit to Adobe, right? That's a journey a lot of founders think about. And, you know, it's a 10x revenue. It's all the things that a lot of founders aspire to. How did that experience kind of shape how you look at new deal flow? Do you think about, hey, could this founder actually sell this to a Fortune 100 company in the US? Or how did that experience shape how you think about the founders and their ability to exit and give a return in a similar fashion to what you generated in the Elaine? Yeah, I learned a lot there during that acquisition and then integration and then the synergy models, right?

30:24Because when you do an acquisition, usually it's for three things. One of the three or several of the three things is like, hey, do I have more product coverage? Do I have like more products offering, a broader product offering? That's IP. It's like some sort of an IP acquisition. I acquire someone to have a broader offering that I can put in the hands of my reps. Or I acquire someone to have a broader access to a market. Oh, you know, these guys are really good in Germany. I need to break into the German market. and this is going to be my foothold, my beachhead in Germany and we're going to leverage that team to be really successful.

30:59Or it's something with customers related. Oh, by the way, they have that amount of customers. We can sell into their customer base or reversely, we can take their product, sell into our customer base. So you have IP product, customer portfolio, geographical coverage, a number of reasons to do an acquisition. So you learn once you go through this, how to really create the synergies that are expected on paper. Because when you do the acquisition, you build these like beautiful models with the M &A team to say, hey, one plus one equals three. Okay, okay, okay. Let's look at that. Yeah, we can have synergies in the back office.

31:40We can, you know, have less HR, less marketing, less finance, blah, blah, blah. We're going to bring the team together. And on the go-to-market side, all of a sudden our reps are going to carry all your products. So you get leverage there. So you build these optimized operating models to get leverage out of that combination of two companies. And when you go through them, there's a reality that kicks in. You have to fire people, for example. You have to have your product being carried by other reps and enable these teams. And it can be pretty brutal to get the teams to adopt. How are you going to make sure that this is going to propagate in the sales teams.

32:21So I've learned there a lot. For example, at Adobe, after we got acquired during the first 18 months, we weren't signing any deals coming from Adobe. Everything we had was in our own pipeline still. Meaning we were generating as an independent business unit the needs and the pipeline for our own deals. But we didn't have someone out of nowhere at Adobe saying, hey, by the way, I have that account in the middle of Nebraska that I'm working on that you haven't thought about that I can bring you. And we could solve. So it took a long time. It finally took off because we had success all of a sudden.

32:59We could show success in certain accounts and we were like evangelizing that success with the reps. All of a sudden the reps were like, oh, wait, if I talk about that with my customers, I can make more money. So understanding the synergies that you can unleash, unlock in a combination of two entities is definitely something I learned a lot. And now that I look at from an investor standpoint, saying, if I invest in this business or if a fund invests in this business, what's our exit path? What does it look like? Where are the synergies? Are they go-to-market? Are they product? Are they geographical coverage?

33:39And how is that going to be perceived in a board of the acquirer saying, hey, give me 500 million, Give me a billion, give me several billions to acquire this business. So once you've been there in that seat, you're able to understand the dynamics and how the decision is made.

33:58Matt Oxley:And as an investor, Stefan, how do you think about the founder? Do you actually do the mental exercise when you meet a founder of a company you're interested in? Are you thinking about, could this person close a$500 million deal with an acquirer? Or is that part of the process you go through? Do you assess the founder not only technically in leadership, but could this person do the deal of a lifetime? Is that part of what you're thinking about? Yes, and it's not specifically linked to M &A. I think this is a question you have as an investor, generally speaking, not just in the optics of an M &A.

34:38It's like, who is that founder? Is this a go-to-market founder? Is this a tech founder? is a financial founder. You can find people out of the different areas. A great seller who's starting his business, a consultant comes from Bain, had great ideas, or you can have a tech geek starting a business. So depending on that, you know that there is areas, skills that that founder will need to acquire over the years to build out a great business and scale a great business. and sorry but just on that are you seeing because obviously in 2001 like you had that skill set you had the grit determination you had the vision you were able to kind of go and dominate of the founders and portfolio companies that you were looking at do you do you see many founders with all of those aforementioned things that are essential to US expansion so it can be a founder or it can be co-founders also a team of funders right personally we did not back in the early days you know in 2001 after have individually all the skills but as a team we were like the avengers you know it's like the avengers we all have a superpower in an area can we have like can that team be an avenger like team and that's fine that's good too you know so But sometimes you have a CEO who's a tech, very often what I see the most is in the space of tech, a tech CEO has a vision for a tech product.

36:18Hey, I'm going to code this and I'm going to then build a business, sell it, scale it, etc. Such a tech founder, with few exceptions, have an expiration date in an organization. Mark Zuckerberg is a tech geek, but he definitely developed over the years all the skills needed on all of the other areas. to scale and just like an amazing business, regardless of what we can think about. So a lot of the tech founders, a business starts, a SaaS business at least, starts as a tech company, as an IP company. That's the first phase of development. The second phase is you need to become a go-to-market machine.

36:59And one is additive to the other, by the way. It's not replacing the fact that you stay innovative and you're a product company, et cetera. No, it's like, in addition, you to be a go-to-market machine, a sales machine. And then the third is you need to become a financial powerhouse also to manage all the finance and the metrics that you have that in order. And that's all additive. So some funders, they're just breaking down when it comes to go-to-market. And I've had that. In my board meetings, it's public information. Out of the six, we've changed three CEOs, funder CEOs out of six. Okay. So that happens.

37:35That's okay. You know. No, those are external people coming in. Or internal people, you know, coming in and stepping up to become the CEO in the next phase of the business. Because these businesses evolve with phases. Because the way that I describe it as well is, I think certain founders slash CEOs get altitude sickness at a certain level. Is that your kind of experience? 100%. And some of these funders, you know, on my six boards, I'm the independent board member. So when you're an independent board member, guess what happens? The founder looking at you saying, hey, we don't want to get in trouble with the founder, telling him he or she should step down.

38:15Hey, you're independent. Can you do it? Can you have lunch with him and tell him that, you know, we shouldn't have his wife run a chair. Okay, great. That's an easy one. We shouldn't have him run the company anymore. He's reached his level of incompetence pretty much. So the independent board member is usually the one having to do that because the funds, they don't want to get in trouble. They want to have a bad reputation of removing funders, etc. So I do that. So you have these conversations and you want to celebrate these funders for what they have accomplished. And I'm going to have a conversation on July 15, by the way, on that topic specifically for another business.

38:55So it's like, hey, I want to celebrate you for what you have accomplished, but your time has come. Your time has come. you need to pass the baton to someone else internally who has shown like the will and the skill we can promote and elevate and take the next phase of the business, right? For example, or someone external that we need to hire. So these are the hard conversations that you need to be ready to have as an investor, especially if you're an independent investor like me, when you don't have your own fund and you bring your operational expertise, people look at you, they look up to you saying, hey, you've been there, you've done it.

39:29I can't you do it again.

39:34Matt Oxley:So Stefan, this has been really great and super helpful. Thanks again for making time to talk with us. You had mentioned talent as kind of being the number one thing you would want people to focus on, the long list of things you need to think about when you come to the US. If you were going to go back and give yourself advice, like before you landed in JFK, if you could go back and give yourself advice before you landed, what would you tell yourself? what direction or what advice would you give yourself before you got off that plane? Don't wait that long. Don't wait that long. Just go for it. Go for it, baby.

40:10Go big. The US is there waiting for you. And it's going to be hard. It's going to break every single bone of your body. But it's worth it. It's worth it. The American dream exists. I've met it. Okay, I know. and you just have to go for it and work really hard and find the right talent to surround you, better people than you and you can get there.

40:38Matt Oxley:Awesome. Well, you've obviously done it as an operator and founder and as an investor. So again, thanks so much for making time to talk with us. We really appreciate you sharing your insights with our listeners and our community. Great having you on the show and we wish you all the best this year. No, and thank you for what you're doing, David, and Matt, with your business. This is amazing. We need more initiatives like that because there's just so much innovation in Europe, and especially in the age of AI right now. There's just amazing talents. There are just amazing businesses. And Europe are small markets, highly regulated.

41:12So the U.S. is just an amazing avenue to grow in scale and business. So thank you for what you're doing there. Absolute pleasure. It's been great to speak to you. Thank you for your time. Okay, sounds great.

From the publisher

In Part 2 of our conversation, Stephan Dietrich moves to the other side of the table. After building Neolane and selling it to Adobe for around $600 million, he now invests his own money in growth-stage software companies and sits on the boards of six of them.

David Rose and Matt Oxley dig into the investor mindset: why he refused to start a VC fund, how he judges whether a European company is truly ready for the US, the single biggest mistake he made in his own expansion, and the hard truths about talent, capital, and timing that most founders learn too late.

If you missed Part 1 (Stephan's founder journey and the two-mile talent playbook), listen it here: https://share.transistor.fm/s/7cbfe0d4


In this episode:

  • Why he invests his own money instead of raising a fund
  • "Smart money": why coachability is his top investment criterion
  • The readiness test: $10M+ ARR, product-market fit vs go-to-market fit
  • Why European products are often too sophisticated for the US
  • The red flag: "we'll just hire a local head of US"
  • Choosing a US city: why New York can cost 30 to 50% more than Nashville
  • His biggest mistake: going to the US too late
  • Discipline: $35M raised, $20M burned, ~$600M exit
  • The real cost of doing business in the US (and why founders under-commit capital)
  • Lessons from the Adobe acquisition and integration
  • Founder "expiration dates" and the hardest board conversation


CHAPTERS

00:00 Intro and Part 1 recap 

01:07 From operator to investor: the mindset shift 

03:06 A health scare and a family decision 

03:51 Why he refused to start a VC fund 

05:02 His guiding principles: evergreen, invest forever 

07:06 Investing as "smart money": coachability first 

08:11 Sitting on the bench: the hardest adjustment 

11:24 How he assesses US readiness (PMF vs GTM fit) 

14:11 Organizational readiness: English and anti-Americanism 

16:10 Choosing a US city: why not default to New York 

17:45 You can't crack the US on $5M anymore 

18:46 Don't half-ass the US 

20:58 His biggest mistake: going too late 

23:23 Go big, but stay disciplined 

24:01 The one gap to master: talent 

27:17 The real cost of doing business in the US 

29:43 Lessons from the Adobe acquisition 

35:11 Founder expiration dates and altitude sickness 

39:34 Final advice: don't wait, go big


About the guest:

Stephan Dietrich is a serial founder and now an Operating Partner at Lead Edge Capital, where he helps European enterprise software companies scale in the US. He guest lectures at Harvard Business School. He co-founded and led the US business of Neolane (acquired by Adobe in 2013), which became Adobe Campaign.


About Scaling Stateside:

Scaling Stateside is the podcast for founders navigating US expansion. Hosts David Rose (CEO, USXP) and Matt Oxley talk to founders and investors who have made the jump, to surface the real playbooks, pitfalls, and best practices.


🔗 CONNECT WITH Stephan Dietrich 

LinkedIn ⮕ https://www.linkedin.com/in/stephandietrich/ 


🔗 CONNECT WITH David Rose 

LinkedIn ⮕ https://www.linkedin.com/in/davidbrose


🔗 CONNECT WITH Matt Oxley 

LinkedIn ⮕ https://www.linkedin.com/in/mdoxley


🏢 POWERED BY WILSON SONSINI 

This episode is powered by Wilson Sonsini, the leading law firm for technology and growth companies. Wilson Sonsini helps European founders navigate US expansion, from entity formation and regulatory compliance to VC fundraising and M&A. Their deep cross-border expertise ensures you structure it right from day one.


US Expansion Partners ⮕ https://www.usxp.co


Scaling Stateside ⮕ https://www.scaling-stateside.com


🔔 Subscribe for more conversations on scaling to the US the right way.


#USExpansion #Startups #Founders #SaaS #GoToMarket #ScalingStateside #Neolane #Adobe

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