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Dylan Serota

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26
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2018-08-17
most recent
2018-08-17
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1
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  1. “I can't wait. We have amazing team, a great service that's taken years to build, and we're just excited to bring Terminal to many new regions and markets across the world. So in five years, I see Terminal being a global brand that's foundational for how the next wave of great companies will scale, while bringing really significant and transformative professional opportunities to people and communities around the world.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “Yeah, mentorship has been really impactful for me, and especially finding people that believe in you and stick with you for the long term, kind of like finding and sticking with a great general doctor. I think it's important to stick with someone and a mentor who gets to know you how you think, what you care about. They can give you the best long-term advice that's personalized to you and not just generalized guidance or just what they would do.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “So, my dad is a lawyer, and he absolutely loves it, so, no hard feelings to any lawyers out there. But for a long time, I thought law would be a really fun and interesting career. And And he told me one day hey, be the one that hires the lawyer. Don't be the lawyer. And I think that definitely made me think more seriously about a business career.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “Biggest myth, I think, is that although we have all this communication technology, that virtual communication is sufficient to build relationships with remote workers, I think, still matters so much. And I believe you have to earn the right to communicate digitally by being there physically. And often people don't invest enough time to be there physically. It is a major commitment of time and travel, but I think it's totally necessary.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “I think marketing is really challenging to work in a distributed model while you need to think about localizing message and maybe having local marketing managers, it can be really challenging to keep everyone aligned on how to build and represent your brand if you distribute too much of the core brand and product marketing resources.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “My favorite book is probably the selfish gene by Richard Dawkins, and I read this for a college course and it completely changed my understanding of almost everything by looking at evolution from the perspective of genes and these tiny codes of information and how all lifeform created is really just trying to replicate that code to live on to the next generation. So evolutionary psychology is fascinating and I think this is the best introduction on the topic.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Looking at it purely as a process and not using the investors that are currently in the room and those out there as people who can help be a barometer for where you're tracking. And I think helping understand the signals and then the market landscape should be an ongoing conversation.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “So I think that really comes down to the type of business you're pursuing and what signals you agree on with your investors are the right ones to indicate you're ready. So where some startups get it wrong is that funding is a process that you just start and finish. And I think it should be a series of ongoing conversations with various VCs to get their perspectives. And that can happen very early. We actually did this basically on day one before we were ever ready to take a check just to learn how the market would perceive the data and metrics we were tracking and it was super helpful and we're continuing to do this now even though we did just announce our round. So I appreciate it. We're excited about the investors we have on board.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “I don't love that phrase, I will say. I think that what you need is really clear goals of what you want to accomplish. You need clear ownership and accountability. And then you got to trust in your team to make decisions which might not always be right. But I think that more decision making and more action ultimately leads to better outcomes because you can adjust and course correct a lot more. So I don't know about necessarily breaking things intentionally, but I do believe in speeds and”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “So there's speed and decision making that I think is tactical, and then there's crafting the right business model and offering for your target customer. So I think the prototyping phase is critical to test quickly, but not rush to market until you really believe you have the right signals that the product and the business model are right. Then you turn on the afterburners in speed of decision making to accelerate your go-to-market and day-to-day operations. And Atomic, I think, is incredible at figuring out this balance for the need of patients in prototyping with the need for speed of scaling when the signals are there.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “So, not a right and wrong. I think that, again, you want to separate what were the outcomes of the decision and then how is the decision made? And oftentimes it comes down to ownership and being able to provide the team both at the leadership level and then at the individual contributor level ownership to make the decisions and making that expressively clear is super important. So when we go back on a weekly basis and look at some of those decisions, we're trying to separate outcomes from process and then speed up the process or clarify ownership across the team to make those decisions happen faster. And that's exceptionally important when you have a distributed team because we're not there to walk up and sometimes ask, hey, should we do this or do that? And so division of ownership and making that super clear up and down the ranks is exceptionally important. And that's what we look to examine weekly.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Decisions and act, the faster the chessboard is now different, and your opponent needs to react to a whole new set of factors. So it's an interesting concept that's been well adopted into military strategy, and I think could be emphasized more in early operating dynamics of a leadership teams at startups.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “I love this question, and I'm really lucky that one of my co-founders, Luke, is an ex-Navy SEAL team leader who's really influenced our team in terms of speed of decision making, especially in times of imperfect information. So this is probably the biggest area of my own development I've had to work on transitioning into founding terminal. But as a leadership team, we examine and scrutinize our decisions weekly, not just based on the outcomes of the decisions, but how quickly we were able to make those decisions and how could we speed up that process in the future. I think that's really valuable time spent. There's actually a really good, I think, lesson from military history on this, which my co-founder, Luke brought to my attention, which was there's this hotshot fighter pilot who could basically beat anyone in a dog fight in 40 seconds or less. And he used a framework called the OODA loop, which is observe, orient, decide, and act. And basically the idea is the faster you can go through that loop, the faster you can win. And the faster you”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “Absolutely, there's the plasticity to move within the company. Everyone doesn't scale at the same linear rate, but I think it's important for leadership to find the people who have that aptitude and continue to give them opportunity and resources to learn and grow. And I think that many people can do that successfully. And I think companies that are able to retain and find those people that can scale with the company are often more successful”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “So, I'm a firm believer in hiring for the problem set that you're facing now and not getting caught up too much in the long term thinking about how this person will work out when the company's double or triple the size. And that's exactly why I think early stage you want to hire more jacks of all trades and less experts from incumbents. So as a company, you don't want to be a jack of all trades, master of none. But with early stage employees, I actually think that those who are less expert but exhibit more interdisciplinary skills can show a higher upper cap on their learning and adaptability and those are the people that I think can be most successful and actually scale their learning in line with the growth of the company.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “Absolutely not. We've actually recently gone through this with a partner of ours TalkIQ that was recently acquired by DialPad. And part of the reason that they were a very desirable acquisition target was purely because they had that team in place in Waterloo that had already been established. The operations were set up. And so I actually think that more companies will look at teams that have the distributed model as a competitive advantage and actually increase the value potential for that acquirer.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “In the cloud. So, I think taking a step back and really evaluating actually what you need from a team, from a process and a tools perspective can get you over the mental hurdle because it's most likely all there in front of you.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “embodied. Absolutely. So philosophically, we hear that companies know they will need a remote team at some point, but think that they're just not quite ready or not quite set up to make it successful. Yet we're at this exciting time, as I said, where all of these technologies are now available, enabling remote teams to, I think, be more successful today than obviously ever before. And so I think a lot of these companies have actually adopted these technologies and practices without even realizing it. To get over that mental hurdle, if you will, one way is actually to, I think, ask a small team of your engineers to work from home for a few days or a week and document what was challenging and then grade their relative productivity. And I've actually seen variations of this done a few times. And often those teams realize they're actually already doing what they need to support remote. They're communicating and documenting in Slack and JIRA using video conferencing effectively. They're able to access all the resources they need.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “Shoulders of engineering leadership to figure out. And while many CTOs and VPs of engineering have faced this problem in previous roles, the talent ecosystems around the world have changed so much, even over the last few years, that it's a whole new ballgame. And it forces that person who should be directing the technology vision for the product to focus on things like traveling back and forth to scope new markets and figuring out office space and negotiating internally with legal and HR to get the operations figured out. And so when you end up putting that into the engineering leadership and to juggle all of those different balls, that's definitely, I think, the biggest challenge and the commonality that we see when companies are deciding to establish a remote team. Another core challenge, though, that we did discuss before as well is actually kind of very interesting, as you said, from more a meta perspective is that distributed teams is more of a philosophical hurdle than a practical hurdle. I mean, what does that really mean and how do you often see this?”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Or overly preserved. It should evolve with the team that you build, a real bottoms up approach. And as that relates to building remote teams, I think companies need to understand that as much as they want to just export their culture to new markets, they really should be equally importing culture from that market into headquarters. I'm not sure who said it or coined the phrase, but I really like it. It's that culture's a verb, not a noun. And I think that's very much the spirit of what I believe in and what can ultimately build longer term strength for a company with respect to culture. So if culture isn't the prohibitor then, Dylan, I'm getting rather confused. What are the commonalities and challenges that really keep you up at night when you think about establishing a remote office for an early stage company? Are there commonalities? Absolutely. that they need to find a new market to build their team. So they're at their wit's end and basically throw this problem on the”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “Office in San Francisco, or when you're making a concerted effort to establish new channels and new pathways. The other thing I think most companies need to change is just over documenting or increasing the documentation that they have of decisions that are being made at various meetings and points and having a repository where someone could look back and see the timeline of those decisions. Those are really helpful. Yeah, no, I love that transparency. But the common pushback I also get is the detrimental impact on culture for having distributed teams. But when we chatted before, and I love this quote, you said companies overvalue their culture. What makes you say this, and how do you think about culture across remote teams? Yes. And to clarify what I mean by that, it's that companies overvalue the culture they have today and undervalue the culture they can evolve into and create in the future so this was a big lesson for me from julia hearts at event that culture should not be stagnant”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Is making that team feel like first class citizens. And this really stems from giving complete product ownership to that team and not just thinking that they'll fix bugs or work on lower priority items. And doing that early on gives that team, I think, a vote of confidence from headquarters that they're equal contributors, which is very important in establishing trust across the offices. Before we discuss kind of the conventional problems that are often associated, one for me that I always get concerned by, it just seamless lines of communication. Often your learnings on ensuring kind of seamless communication flows between distributed teams. So one of the, I think, most important factors is time zone alignment. I think what we've heard from feedback is the more hours that you have to synchronously communicate, whether that's over Slack or other tools and systems. That's one of the most important factors. And then obviously, I think we're at this stage in time where a lot of those technologies are just being adopted, whether it's in your core.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “So, there's many aspects here. I think first, market selection is key. So, understanding where you want to take your team and the right place for that team to grow. And there's a lot of factors that go into that in terms of talent. How big is the talent pool? Who are the incumbents in the market with large engineering teams? What technologies are popular in that city or that region? What universities are local there that could feed into the long-term potential talent pool? How aligned are time zones? How easy is travel? So there's a lot from overall market selection, but from a team standpoint, there's no question that you need strong initial leadership for that team to be successful. So hiring the first senior tech lead is critical. It doesn't have to be the first hire, but I think it does need to be in the first view to establish a strong foundation for that team and allow that lead to start making some of the hiring decisions with local knowledge of talent on the ground. And lastly, and I think a very important factor.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “80, 100 engineers, and that's much more difficult to actually re engineer your practices and divisions of responsibility, or you now have a dated tech stack that makes it increasingly hard to find engineers that are actually excited to build upon the technologies you're using that may just be a few years behind the modern trend. Absolutely. It seems so much easier to insert that kind of culture and discipline from day one. I promise this isn't a light speed advert though, but I did speak to Nakule before the show. With that in mind, and the benefits you just posited, what are the key aspects to making”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “Absolutely, great question. So I think simply building a company in one market like Silicon Valley is harder than ever before to sustain. In fact, I think it's unsustainable for 99% of the companies out there. Talent is obviously the most precious resource for a technology company. And being isolated in one market actually poses massive long-term risks to a company's ability to compete, especially with high attrition rates of employees or the risk of a new overnight unicorn that can take up significant portion of the talent from the ecosystem. So we believe geographically diversifying or building teams across multiple markets is a muscle memory that you should start building much earlier than conventional wisdom would suggest. And we're seeing companies now do that on day one or with employee number one. And I think that trend will only continue to be the norm. And we've spoken to companies that wait to do this much later when they have 50.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “No, it's a great question, and believe me, it was a tough choice to leave Evite after so many years and learning so many different parts of the business from sales to strategy to product. But to be honest, I went to Kevin when I was interested in leaving and we had a very frank and honest conversation about what the opportunity would be like. And both him and Julia were incredibly supportive. And so I felt like I had their vote of confidence. It was absolutely the right time to make a change. I did also speak.”

    2018-08-17 · The Twenty Minute VC · 20VC: Why Founders Must Use VCs as a Barometer, How to Make Distributed Teams Work Successfully & The Biggest Mistake People Make Early In Their Career with Dylan Serota, Founder @ Terminal · IDENTIFIED FROM THE TRANSCRIPT · source