The DroidDevCast

Technology Startup Observations with Adam Schoenfeld

Episode Summary

On this episode of The DroidDevCast podcast, Esper Platform Evangelist Rin Oliver sat down with Adam Schoenfeld, VP of Strategy at Drift. Adam is well known for his role as the Co-Founder & CEO of the B2B Marketing startup Siftrock, a bootstrapped email and marketing service that Schoenfeld later sold to Drift. As a three-time founder, Schoenfeld is no stranger to both success and failure. He currently leads Drift’s strategy and product development roadmaps, in addition to leading the company’s efforts to develop new product lines. In addition to his role at Drift, Adam also is the Host and creator of the, ‘Built in Seattle’ podcast, which features guest speakers from the startup community within Seattle, Washington. Throughout the episode, Schoenfeld highlights not only his expertise in the startup ecosystem, but offers advice to other entrepreneurs, starting with a need to focus on solving problems for the customer.

Episode Notes

On this episode of The DroidDevCast podcast, Esper Platform Evangelist Rin Oliver sat down with Adam Schoenfeld, VP of Strategy at Drift. Adam is well known for his role as the Co-Founder & CEO of the B2B Marketing startup Siftrock, a bootstrapped email and marketing service that Schoenfeld later sold to Drift. As a three-time founder, Schoenfeld is no stranger to both success and failure. He currently leads Drift’s strategy and product development roadmaps, in addition to leading the company’s efforts to develop new product lines. In addition to his role at Drift, Adam also is the Host and creator of the, ‘Built in Seattle’ podcast, which features guest speakers from the startup community within Seattle, Washington. Throughout the episode, Schoenfeld highlights not only his expertise in the startup ecosystem, but offers advice to other entrepreneurs, starting with a need to focus on solving problems for the customer.

Episode Transcription

Rin Oliver (00:07):

Welcome to The DroidDevCast, a podcast brought to you by the team, Esper, bringing you the latest news, thoughtful discussion and insights into all things Android, Android DevOps, and open source software development. I'm your host, Rin Oliver, platform evangelist at Esper, and today I'm joined by Adam Schoenfeld, VP of strategy at Drift and the host of Built in Seattle podcast. Adam, thank you so much for joining me today.


Adam Schoenfeld (00:26):

Thanks for having me Rin, it's good to be here.


Rin Oliver (00:28):

You're very welcome. We're here this week to learn a little bit more about Adam's journey as an entrepreneur and to get his observations on technology behavior, and of course, tech startup observations. Let's get started. Adam, tell me a little bit about you. What have you done and what are you working on currently?


Adam Schoenfeld (00:41):

I've been a three-time founder with various levels of success, and most recently co-founder of a company called Siftrock, that was bootstrapped company in the email marketing space, and I sold that to Drift and Drift is in the conversational marketing space where we have a chat and chat bot product that's been really popular and I've joined there as a VP of strategy and products. And so, I work on the product strategy and roadmap as well as lead our newer product lines, which is serving sales users. So I've been at Drift for about two years and before that I spent a lot of years trying, and failing, and doing some things good and some bad in starting companies.


Rin Oliver (01:27):

That's actually really interesting. Some things good and some things bad is the general antithesis of what makes a startup, I would think some fail, some don't. What would you say is something that you've learned from the ones that failed?


Adam Schoenfeld (01:38):

Oh man, so much. I think that having a good relationship with outcomes is important in doing startups because the math is against you. The odds are that you will fail. And so, early on, when I first started a company, I just thought that my ideas were great, because I'd read TechCrunch that the company would be amazing, but I quickly realized that just it wasn't about generating ideas that had to be close to the customer. I think that was the lesson from my first startup, is the need to have a customer and to really deeply understand the customer and solve for that customer. I had a lot of creative energy, but I had no common sense about what it takes to create value in a business.


Adam Schoenfeld (02:25):

And so, that company ended up shutting down and I took that lesson forward to my next company, which was a rollercoaster of a ride and had some really good high points as well as some lows. But in that company I took the lesson about focusing on customers and brought it to the forefront of how I worked.


Adam Schoenfeld (02:43):

In the second company, I think the big lesson was about people. And I think that I still believed through that journey that ideas and execution were paramount, and I think what I came away from that learning was that it's all about people, not just who you hire, but how you work as a team, and how you build culture, and all the people decisions ended up being when I looked back the most important, including the relationships with co-founders, the formation of the leadership team. So all those things became really front and center for me after the second company.


Adam Schoenfeld (03:22):

After the third company, honestly, I'm digesting the learnings from Siftrock. I think it was a great business and we did a lot, but sometimes probably we underestimated our potential. So I think having a good balance between conviction and humility is probably the thing that I'm still trying to process from the third one. And it's funny because you look back on history and you create all these narratives, and I think the narratives are constantly changing even though the facts of the situation didn't change. So I look back on all the experiences now with what I've learned and it keeps changing, my takeaways continue to evolve, which is interesting.


Rin Oliver (04:02):

That does sound really interesting, and I agree that it's all about people. I have a lot of thoughts about culture, and culture fit, and all of those things that I don't think we have time for today fortunately, that's another podcast. But speaking of podcasting, you're well-known for The Built in Seattle podcast, what are some of the most memorable advice that you've gotten from Seattle founders? What have you learned from founders in Seattle?


Adam Schoenfeld (04:27):

It's been a fun project I've done for about a year now where I interview entrepreneurs, investors, executives at startups in Seattle. The reason I did it in Seattle, this is funny, is because I just wanted an excuse to get out of the building and go meet with people in person. And so, all my early episodes, I was coming to people's offices and recording in person, of course, that changed with the pandemic, but I've continued to find value in having those kinds of conversations, and I've been very fortunate to have access to some of the top leaders. I've Interviewed four founders of companies that are worth over a billion dollars, I've interviewed-


Rin Oliver (05:03):



Adam Schoenfeld (05:05):

... incredible group of folks, some of the top investors including like McIlwain of Madrona, and then a lot of the up and coming companies, companies that have raised 20, 30, 40, $50 million and are in that middle range like Crowd Cow or Usermind, or Esper. I talked to Yadhu, your CEO. And I think in terms of the lessons, I could give you a long list so you can stop me or you can prompt me to go more, but one of the ones that really stood out was I think a lot of the really successful people have a more nuanced view on humility than I have had in my life. It's not that they just say, "I'm not so great," it's that they really go deep into learning from others, they're really good at inquiry, they destroy their own ideas as Charlie Munger and Warren Buffet talk about, and they're good at listening and learning quickly.


Adam Schoenfeld (06:02):

So I've realized that they have this more advanced view of humility. I was surprised that none of them come across like, "Well, I'm so successful. I run a billion dollar company, so I'm in a different class of people, so you should treat me differently," or "I'm some special person." None of them have that mindset, they're all continuing to learn, continuing to push themselves and challenge their ideas to listen and to learn from others. So I found that to be really eye-opening in how they thought about humility, how they assess their own ideas and how they learn from others. That's probably been the biggest.


Adam Schoenfeld (06:45):

A smaller one, but related is most of them see time differently. They have an infinite horizon, so they play the infinite game if you're familiar with finite versus infinite games, and the really successful people are doing this for 10, or 12, or 15, or 20 years before they really become known as a successful company. And so, the company builders and founders that are coming in early, they're able to take that very, very long-term view, and I think that they're able to really put that above any sort of short-term or finite games that they're playing in how they operate and how they make choices all along the way.


Rin Oliver (07:26):

I agree completely. In writing, we actually call that ability, kill your darlings. If you love something, you can delete it, if it doesn't further the story forward, you just get rid of it. It's okay, because you have to accept that even though you think something's perfect, your reader won't.


Adam Schoenfeld (07:39):

I love that.


Rin Oliver (07:40):

And you have to be able to have your hoovers and say, this is not serving the story, it's not moving things forward, and so it needs to be cut. So I think that having the capability to sit back and say, "This isn't working, what can we do [crosstalk 00:07:52]."


Adam Schoenfeld (07:53):

It's hard though, because we fall in love with our own ideas. It's like the Richard Feynman quote, the first principle is not to fool yourself, but you're the easiest person to fool, and I think that that's so true and we fall in love with our own ideas and we get stuck in that pattern.


Rin Oliver (08:09):

Too true. What are some startups and emerging technologies that you're really excited about that are coming out now?


Adam Schoenfeld (08:16):

I love the no-code low-code space. I'm an investor in a fund, in that space, I think that's really exciting what you can do with no-code and low-code now. I still love marketing tech. I've been working in marketing tech for a long time, and investors, a lot of them hate marketing tech because there's seven or 8,000 different vendors playing in the space. But I think that's one of the reasons I love it because there's still a lot of unsolved problems, and I don't know that it's really cemented in terms of the CMOs top three must haves, and I think that's still very fluid and certainly Drift wants to be there, and I think has a great chance to and is certainly proving that in our current stage of the business. But I still think there's lots of opportunity in different parts of marketing tech. So those are the ones that I'm probably thinking about the most right now.


Rin Oliver (09:12):

Absolutely. And in terms of marketing tech, what's the tool that's come out recently that you're just like, "This is going to change things," are there any?


Adam Schoenfeld (09:20):

In marketing tech specifically? I don't know, I think that's the problem with the space. I don't want to toot Drift's horn, and the founders of Drift very identified a really big trend to latch onto, but I haven't seen a lot lately that I'm like, "This is changing the game." I think a lot of it's pretty incremental, and that's one of the things I like about the space, is there's still a lot of opportunity there. I think this whole virtual events thing is going to really change marketing tech, and I don't think anybody's nailed that yet.


Rin Oliver (09:48):

For sure. No, not even close. No, that's a long game for sure.


Adam Schoenfeld (09:54):

So that's one that will be an interesting subsegment. I still think email is really interesting. Everybody needs email and there continues to be good innovation in email marketing, but it hasn't really had a second wave or a third wave maybe is the right way of thinking about it, but I still think email is important.


Adam Schoenfeld (10:15):

I think watching what Segment was able to do with their customer data platform was really compelling, and they just got bought for a huge number. I can't remember if it was two, or three, or whatever billion, or one billion, but it was a huge outcome and I'm blanking on the number, but they got bought by Twilio. And so I think this whole data space is still nascent, and I think the whole CDP layer is undefined. It's funny, I should have an answer to that. If something that's caught my eye as changing the game, but I haven't seen that. I think it's a lot of incremental stuff and companies are still piecing together 15 or 20 vendors usually.


Rin Oliver (10:54):

In terms of virtual events, actually, this is something that I'm lucky in my background has actually prepared me for, because I have a background in the games and e-sports industry from way back. And so, I feel like the people that are now in DevRel and now in community that may also share that background are in a little bit of a better position just because e-sports up until recently were by and large prerecorded virtually and you had to have that virtual aspect. So it's one of those things where it's like, I did not think those would intersect, but now they have.


Adam Schoenfeld (11:25):

What a funny meeting of your different domains, between marketing and e-sports, that's one of those combos where you get this unusual edge from combining two different things.


Rin Oliver (11:38):

Exactly, I thought it was very interesting. And based on your experience, do you have any advice to founders or potential founders that are hoping to get into maybe starting their own startup?


Adam Schoenfeld (11:50):

Oh man, I think I'm not great at dispensing advice. I'm middle of the road at best in my track record, but certainly trying to learn as I go. I think the advice that I would give a founder who's thinking about it, or maybe myself before I had gotten into this crazy mess, first I'd probably say, think of the pursuit as the prize, think of the climb up the mountain as the reward, rather than the top, because the relationship you have, the outcomes is so important because of the odds, because how hard it is.


Adam Schoenfeld (12:27):

And so, if you're only focused on some external reward, then it's probably going to suck a lot along the way. And even if you win, then you're going to get the reward and it's probably still going to not feel any better. So I like to think about, "Am I doing a good thing?" When I interviewed Glenn Kelman, and asked him about his hard days, he said, when he goes home to his partner and he talks about the hard times and she asks him, "Are you doing a good thing?" And he's like, "Yeah, absolutely, we're doing a good thing." And it's like grounding and stuff like that. I like to think of, "Would I be proud of this if it failed," or "would I still do it if it failed?"


Adam Schoenfeld (13:08):

And I think if you can't come up with answers to those things, then it's all about some kind of external prize, it's going to be really rough. I like to think of the grammar test, just like with my grammar, I think this is a good thing worth doing. It doesn't have to be solving some environmental problem or curing cancer, but it has to be something that you feel is like a net positive for someone else in the world, and you can usually affect your customers and your employees even on a small scale.


Adam Schoenfeld (13:37):

So that's probably what I would advise to... And I do give a flavor of that advice when people call me about it too, people are thinking about starting a company is to get clear on why you're doing it and inspect or interrogate the relationship you have with your outcomes.


Rin Oliver (13:55):

Absolutely. I actually also have a growing small business with my wife, and we've noticed that there's a few parallels in what you just said between having a small business and being at a startup, I think it's interesting because there is that, "Are we doing something worthwhile?" Texts happening a lot, and the journey itself has been really interesting, and I think that there's a lot of parallels, especially in e-commerce to startups too.


Adam Schoenfeld (14:19):

Absolutely. I think that's true in any creative or entrepreneurial pursuit, because it's hard to go against the grain and it's hard to break out from the consensus or the conventions. And so, if you think in terms of the pursuit and the process and take that as the reward, I think you have an advantage over people who think about the outcome only, it lets you be more fluid and flexible in how you go about it and stay focused on your values and how you want to be rather than just playing to win or get some prize.


Rin Oliver (14:51):

Absolutely. And for those students of startups that we've heard of, what does it mean in your experience to be a student of a startup? What's that like?


Adam Schoenfeld (15:02):

I'll tell you the origin of it. I got that from, there's an analyst that I really like, guy named the name of Dan Gottlieb at Topo, and I remember hearing him saying, "I try to be a student of the game at all times," and I was like, "Oh, that's a great way of saying what you do." And I think I try to be a student of startups or a student of business. I try to learn about businesses, what makes them work? What makes them tick? From this time, as well as I try to get outside of this time period and outside of this domain as well and look at Danny Meyer in the restaurant space or look at just people and how they succeed and what makes them tick. And so, I try to just act like a student in terms of trying to learn and understand the reality of businesses and startups.


Rin Oliver (15:49):

Absolutely. And given the current situation that we're in, people might not find themselves with a lot of time to learn. They may be experiencing burnout, especially if they're already at a startup. Startup life is hard. What would you say to those people to find the time to be a student? What are some tools that you recommend to help people prioritize that, "Oh, work-life balance thing," especially in the current pandemic situation?


Adam Schoenfeld (16:13):

No kidding, I think the vines have gotten very blurred, at least I have young kids, so in my house it's like there is no line, they could run in here at any time and start screaming and plus you don't have that commute or that distance that gets created. It's a tough time in a lot of ways. I think we have to give ourselves some grace. I think that it's okay not to really achieve the most possible during this current time. I think having some grace and some space is really important, at least I'm trying to do that with myself and not driving myself to the max at all times.


Adam Schoenfeld (16:51):

But with learning, for me learning gives me energy, so it's on the other side of the ledger. If I have time to read, if I have time to listen to great interviews, if I have time to learn from others, that's giving me energy. So I think that's probably, for me personally, one component of it is that's the time I have to re-energize. And then I would say to the extent you can integrate it into your work. That's the highest leverage because at least for me, I've found that learning is great in concept, but the rubber hits the road on practice and how you integrate principles into what you do.


Adam Schoenfeld (17:28):

So if I can get reps and sets on something bigger that I'm thinking about, or working on, or learning about in my day-to-day work, or day-to-day life as a parent, or a spouse, or whatever roles I had played during the pandemic, then I think that's where a lot of leverage comes because so much of learning is like practice, reps and sets, trying and failing, experimentation. So I think bringing that in, even in a very small way is probably the most bang for the buck opportunity.


Rin Oliver (17:59):

Absolutely. I agree completely. In reference to your current role, how have you seen the state of self-service evolve since the onset of COVID?


Adam Schoenfeld (18:09):

Wow, a lot more digital. I think whether it's full self-service, product-led growth, or whether it's just people getting educated on a company or engaging with a company digitally, it's just way more. We just talked about virtual events, we don't have events. So in our world, in B2B, it's like events were a huge thing, and you'd meet people at this conference or that conference, and if you're a field sales rep you would fly in and you'd take them out to dinner and all those activities are gone.


Adam Schoenfeld (18:38):

And so, I think that the focus is just more and more on digital marketing, digital experience, and whether that be self-serve or assisted, that's where most companies are spending their time. I don't know how to quantify it, but it went from a mix between the two to entirely digital. And I don't know how much it swings back, but certainly right now if you're not building your sales and marketing systems around digital, you're going to be missing out on a lot.


Rin Oliver (19:09):

Absolutely. I agree completely. Definitely, building digital events is something that we're going to be focusing on next year, Esper a little bit too, that's exciting.


Adam Schoenfeld (19:20):

I'm excited to see what you do. I'm still waiting for one to really just define the model and be like, "This is how it's done," and this is a great virtual experience. It's so hard to replicate some of the goodness that you get from showing up in a Zoom type environment.


Rin Oliver (19:36):

I've been to so many CoopCons and there's CoopCon North America virtual this weekend, they're not the same, they're not the same at all, and it bums me out.


Adam Schoenfeld (19:46):

Do you miss the events?


Rin Oliver (19:47):

Yeah. I can't even put into words how much I miss CoopCon because I've spoken at them and not only I wasn't a speaker, but I've also been a pod mentor and I've done so much in the Kubernetes community, and I've gotten so much back, and being involved in the Kubernetes community is something that's absolutely changed my life, and I miss all my friends and it's hard. It's hard not to see the people that you've gotten to know over the last two years that have been there throughout the highs and lows of your career and that have helped you grow as a person, and I just I miss that.


Adam Schoenfeld (20:18):

I think that's a great observation, because so much of it is about that community and that multiterm relationship that you have with people there. Some people go to events in a very transactional way, like "I'm going to try to get business, or "I'm going to try to run a booth and leave." But what you're talking about is I'm the same way, the events that I go to it's because I've gone to them multiple times and I know I'm going to see certain people there and it's going to be fun and enriching in a long-term way, and that's really hard to replicate in a virtual room.


Rin Oliver (20:49):

It's very hard. I hope we get to do CoopCon in person next year, that'd be good. Fingers crossed.


Adam Schoenfeld (20:56):

Fingers crossed, bring the vaccines.


Rin Oliver (21:01):

Pfizer please. Lastly, what gives you hope for the future of startups? What's the thing that you're really holding onto in terms of the startups that are going to go places in the future?


Adam Schoenfeld (21:15):

I think looking at my kids gives me hope for the future because despite all that's going on in the world, they still ask great questions, they're curious, they're much more curious than any adults I know, and that's what it's all about, and I think they're going to get through this, they're incredibly resilient and we'll all get through this, and I think we'll keep innovating, we'll keep being creative.


Adam Schoenfeld (21:38):

So I think these are tough times for a lot of people, and I don't want to discount that, and I recognize I'm also in a place of extreme privilege that my company's doing well, and then I have a job and that I have a yard where my kids can go run around so that they can still actually have things to do that aren't just looking at an iPad. But I think we will get through this and creativity and innovation will continue as it has. And I think a lot of good companies will get founded in this too, because we've been talking about just this one problem, virtual events, but extrapolate that out to education, and healthcare, and everything else in the world that is just under intense pressure right now, and I think there's going to be a lot of really interesting companies that probably come out in the next two, three years.


Rin Oliver (22:23):

Absolutely. Well, Adam, thank you very much for joining me, I really appreciate it.


Adam Schoenfeld (22:27):

Thank you Rin, I appreciate you doing this.


Rin Oliver (22:29):

Thank you so much for joining us on this episode of The DroidDevCast, we'll be back next week with another exciting show for you, just remember to like, subscribe, and share this episode on social media. You can also follow us on Twitter @esperdev and subscribe to our YouTube channel to keep up with all the latest happening here at Esper. You can listen to The DroidDevCast on Apple podcasts, Spotify, Simplecast, wherever you get your podcasts from. Thank you again [inaudible 00:22:50].