Inside Pioneer with Sacha S. (Lolly)

An interview with Sacha S., the former Founder & CEO of Lolly (backed by SV Angel), regarding his experience participating in Pioneer.
February 24, 2024
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Sacha is the former Founder and CEO of Lolly, a social dating application. Lolly was backed by SV Angel, the former CMO of Sequoia Capital, and the former CEO of Apple. Sacha applied to Pioneer with a different idea before pursuing Lolly during the March 2021 cohort. Sacha has since moved on and is working on a new startup currently in stealth. I talked with Sacha about his advice to people applying to Pioneer, what they look for in applicants, and how the Pioneer team supports startups.


  • Pioneer indexes on how fast you can ship and iterate.

  • Pioneer’s accelerator leans technical, with most founders having engineering backgrounds.

  • Pioneer’s Demo Day didn’t help Sacha raise money, but the pitch feedback he received from Vinod Khosla was valuable.

  • Pioneer is a very tight-knit community – the first thing Sacha did when he moved to San Francisco was text the Pioneers he met in his cohort.

Interview Transcription

Edited lightly for clarity

Kieran: Thanks again, Sacha, for joining me today. Can you introduce yourself?

Sacha: My route into startups is pretty circuitous. I started in neuroscience. I did about 8 years of research starting when I was 15. I ended up not getting my PhD. I left and started a consumer app called Lolly. Just prior to that, I got into Pioneer, and that was really a life-changing experience where I really fell in love with company building. I used that as a springboard into that company, where I met my co-founder, Mark. He found out about me through Pioneer. We started Lolly and raised a few million dollars. We ended up not finding PMF, which was a frustrating conclusion to that journey. I left that and have since started a new company. We are currently in stealth, but we were accepted into YC. So, I can talk about that process as well.

Kieran: Are you able to share what industry (your new startup) is in?

Sacha: No, I have to keep it under wraps, unfortunately.

Kieran: Why did you get excited to apply to Pioneer in the first place?

Sacha: I heard about Pioneer through one of my best friends in San Francisco, who hadn’t applied but knew a ton of people who were involved with the development of Pioneer as a program. It was weird; I was like a neuroscience nerd – I had no insight into the startup space whatsoever and didn’t even realize that being a startup founder was a viable path. It was really just my first foray into it. The initial impetus for applying was just the idea of nucleating smart people and getting a lot of surface area with those smart people. That was a very exciting prospect for me. That was the MO. I went through the whole kind of competition thing, which Pioneer doesn’t have anymore, but that was a great process because it formalized the process of company building, especially in the early stages. That was helpful for me.

Kieran: What was the most valuable piece of advice you received during the program?

Sacha: That wasn’t the value add. I would say some of my favorite people I ever met came from even the first month of Pioneer. So it came down to the people; it wasn’t per se advice, even remotely close.

Kieran: You mentioned you met your co-founder through the program. Can you talk more about how that happened?

Sacha: So, the project I got into Pioneer for was 1 of maybe 10 that I was building at the time. I was kind of coding like 16 hours a day – just trying to put stuff out there in the world. I think Pioneer taught me to put things out there, which I normally wasn’t doing. I was sitting on dozens of repos of products that I wasn’t publicly announcing. So, anyway, I started putting stuff on my website, being a little more public about the things I was building, making YouTube videos, and so on. The guy who became my co-founder, Mark, knew one of the guys in Pioneer. This Pioneer and I had been talking because our projects were pretty synergistic, and we discussed a potential collaboration there. As soon as he met me, he was like you have to meet Mark; you have to meet Mark. I met Mark and we had immediate chemistry. He had seen everything I posted about, my projects, etc. This was a serendipitous outcome from something I didn’t expect at the onset. I was just building because I was obsessed with it, and adding it to my website was just a secondary thing. It ended up being kind of a calling card for Mark. The rest is history.

Kieran: Pioneer’s Demo Day is structured as a 1:1 pitch with a top investor. I remember watching your YouTube video with Vinod before this. What else happens on Demo Day?

Sacha: I don’t know, nothing. For me, as it related to me and my pitch, you just show up for a 5-minute slot – it’s actually pre-recorded, that’s another funny twist – and that was it.

Kieran: Do you think that structure or format helped you raise money?

Sacha: No, but seeing the caliber of investor Vinod was incredible. I won’t say he eviscerated me, but he definitely pointed out the chinks in the armor very readily, and I really appreciated him. I have a tremendous amount of respect. It was pretty awesome to see.

Kieran: Yeah, he tried reframing your pitch, which was probably helpful advice at that stage.

Sacha: Totally, 100%.

Kieran: What advice would you give to someone applying to Pioneer?

Sacha: You should be extremely excited about the prospect of being with other smart people who are extremely passionate about what they are doing. I would say the value prop is predominantly that, and Daniel Gross is phenomenal – so is the rest of the team, Rishi, and so on. The main prospect you should be riveted by is being around smart people who are super passionate and weird Internet nerds. If that’s the community that gets you excited, then you should 100% do it. But, yeah, you should also have a sober perspective about, like what it is going in.

Kieran: Can you talk about your interactions with the Pioneer team? Daniel, Rishi, etc. Was it structured so you’re meeting with them bi-weekly, or was it really ad-hoc where when you needed help, they were there to help?

Sacha: For Daniel and Rishi, it was the latter. We had an amazing community builder named Jackson Prince. To this day, he’s a legendary figure amongst the circles. He was running amazing weekly organized sessions, and we’d also have intermittent visitors come in and have long-form discussions with them. We could have a long Q&A. I remember grilling Laura Deming on a few longevity things, and that was an awesome experience. They bring in high-caliber founders and investors to give talks and have an informal Q&A at the end. But, in so far, as it related to the organized activities, it predominantly was led by Jackson. He since become a founder and went through Pioneer himself. So, it’s kind of a funny end to that story.

Kieran: Now that you’re finished with the program, do you still engage with the Pioneer community in any ways? Or how do they organize?

Sacha: So I just moved from New York to San Francisco. The first thing I did was text my fellow Pioneers. This is a very tight-knit community. At least I can speak to my cohort, which was kind of peak COVID, and we still became very close. The community is very strong.

Kieran: Is there anything that I didn’t ask about that’s important to know for someone who’s considering Pioneer?

Sacha: At least when I was applying, there was an emphasis on having a technical tilt. Most of the people applying, or the Pioneers, were engineers. I definitely have a semi-sober perspective on that. It’s entirely that’s changed. It’s entirely possible that was coincidental. Definitely, the majority of folks in Pioneer were engineers. So, keep that in mind if you’re applying. If you’re on the more technical side, I would definitely apply. If you’re not, it doesn’t preclude you from applying, but I would probably seek out someone who can help you ship at a high velocity because that’s what Pioneer looks for – how fast you can ship and iterate. You’re a bit shackled in that sense if you’re not technical.

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