Rin Oliver

November 24, 2020

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.

Solving for the Customer in Startups

Solving for the customer can look very different to each individual startup. Schoenfeld noted that although certain technology websites told him that his first startup idea would be, ‘Amazing,’ it ultimately ended in failure. This, he explained, was due to a lack of ideas that were customer-centric. “I think that was the lesson from my first startup, is this 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 sense. I had no common sense about what it takes to create value in a business,“ said Schoenfeld. The key thing that Schoenfeld took from that experience and brought to his second startup was the need to not only have a customer in mind, but to actively focus on solving problems specifically for that customer. 

An additional lesson Schoenfeld took away from that experience was about the people in your company. Not just in terms of hiring, but in terms of team leadership, cohesion, and how you work together as a unit to achieve your goals. In particular, building a successful team starts with understanding what makes your startup’s culture stand out, and being able to clearly communicate, act on, and adhere to those values. 

Schoenfeld is still going through the learning process in regards to what he achieved at Siftrock. “Having a good balance between conviction and humility is probably the thing that I’m still trying to process from the third one. And, you know, it’s funny, because you look back on history and you create all these narratives. 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, and my takeaways continue to evolve, which has kind of been interesting,” said Schoenfeld.

Learnings from the Built in Seattle Podcast

In his time interviewing many of Seattle’s most successful startup founders, Schoenfeld noted that the most interesting trend he noticed among his guests was that of humility. Rather than having inflated egos due to their business success, the founders that Schoenfeld has spoken with on the Built in Seattle podcast are down-to-earth, empathetic, and always looking to learn from others. Another trend among guests was that of the tendency to adopt the writing concept of, ‘Kill Your Darlings,’ meaning if something isn’t working, no matter how attached you are to it, it’s best to scrap it and move on.

“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 sort of destroy their own ideas,” said Schoenfeld. In addition to this, Schoenfeld went on to explain that many of the founders he has spoken to view time differently than most. Rather than seeing the clock as running out, the successful founder is in it for the long haul, seeing time as infinite, with infinite opportunities available to them. “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.” 

Breaking from Convention and Managing Emotional Workloads

When founding a startup, Schoenfeld noted that it is critical for founders to understand that the journey is not only about the destination. Getting to the top of the mountain as the only goal means that one would miss the journey of the climb itself. “If you’re only focused on some external reward, you know, then it’s probably gonna 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,” said Schoenfeld. 

In a, ‘Built in Seattle,’ podcast interview with Glenn Kelman, Schoenfeld highlights the need for founders to keep grounded during the hard times. “He said, when he goes home to his partner and he talks about the hard times, she asks him, ‘Are you doing a good thing?’ And he’s like, ‘Yeah, absolutely. We’re doing a good thing.’ Right. And it’s kind of like grounding and stuff like that,” Schoenfeld explained. While founding a startup is a highly stressful endeavor, one must always take care to understand that at the end of the day, it’s about being proud of what you’ve created, rather than getting an external reward such as fame, fortune, or other recognition. “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”

Thinking about the pursuit and the process as the reward, rather than chasing external rewards, is critical for startup founders to keep in mind as they progress on their journey. By breaking from conventional ways of thinking around startups that focus mainly on external motivation, founders are able to stay focused on their goals, be more flexible and are able to pivot or change their course of action quickly, and can better stay true to their values.

Being a, ‘Student of startups and businesses,’ as Schoenfeld often says, means that one must always commit to learning and developing their skills whenever possible. “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 sort of the time I have to re-energize. 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.” 

In this Episode of The DroidDevCast: 

00:39 – Can you tell us a bit more about who you are and what you’re doing currently?
01:34 – What have you learned from your startups that failed?
04:02 – What have you learned from fellow founders in Seattle?
08:10 – What are some startups and emerging technologies that you are excited about right now?
11:38 – Do you have any advice for potential founders?
14:52 – What does it mean to be, ‘A student of startups?’ 
17:59 – How have you seen the state of self-service evolve since the onset of Covid-19?
21:00 – What gives you hope for the future of startups?