Safwan Masood on Free Ventures

An interview with Safwan Masood, the Managing Director of Free Ventures, on how they support student founders and how to join the team at Cal.
February 24, 2024
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Safwan Masood is a senior at UC Berkeley, double majoring in Data Science and Economics. He joined Free Ventures his sophomore year and is now the organization’s Managing Director. Free Ventures is a student-led non-profit at UC Berkeley that runs a startup accelerator with no funding attached every semester. The organization has been around for 11 years, and its portfolio has raised $170 million in follow-on capital from investors like Y Combinator, Pear VC, SV Angel, and more. I talked with Safwan to learn more about how Free Ventures supports the founders they work with and how to join the internal team.


  • Free Ventures is positioned to support pre-seed startups at the earliest stages, often taking companies at the idea stage. 

  • Free Ventures looks for founders who can articulate a compelling story of why this is a big problem, why they’re passionate about solving it, and why they have the right team and approach to solve it.

  • Free Ventures recruits internal team members each semester. The interview process consists of a written application and two rounds of interviews. While startup experience is not a prerequisite to joining, most team members have worked at a startup or tried to build a startup themselves.

  • Safwan noted that one of the largest areas of improvement he sees is improving the cohesiveness of the Cal startup ecosystem. Free Ventures is committed to working with other startup organizations on campus to increase awareness and accessibility to entrepreneurship.

Interview Transcription

Kieran: Thanks, Safwan, for joining me today. To kick us off, do you want to introduce yourself?

Safwan: Kieran, thanks so much. My name is Safwan Masood. I’m a senior at UC Berkeley studying Data Science and Economics. I’m also the Managing Director of a pre-seed startup accelerator, Free Ventures. We’re a zero-equity startup accelerator and take in a couple of companies per semester. These are all student founders. We try to help them get from zero to one (by supporting them) with funding, customers, finding co-founders, etc. Whatever it might be, we’re trying to help student founders build and scale their startups on campus.

Kieran: How did you first learn about Free Ventures?

Safwan: When I first came to college four years ago, I had no idea what Free Ventures was. (In fact,) I had no idea what startups were at all. I came to college as a Political Science major and wanted to attend law school. Halfway through my first year, I stumbled into tech. I took a data science course and ended up liking it. I switched my major to data science. COVID hit my first year, so I took a gap year. I worked at a startup for a year as a product manager at an early-stage company. I was super interested in what startups were, and it intrigued me. So, when I returned after my gap year after the startup had closed up shop, I wanted more. I wanted to be involved in the startup space on campus. I was looking for organizations to fit that need and stumbled upon Free Ventures through a couple of mutual friends in the org. I thought the work they did was super cool. They told me, “Hey, we work with actual companies, we work with the founders, we help them build and scale their ideas.” So, I found out about it midway through my sophomore year. I ended up applying to the internal team and getting in. So, I’ve been there about a year and a half now. I’m loving every second of it.

– let’s start with questions directed to help student founders considering working with Free Ventures – 

Kieran: You have a two-step admission process: a written application and a 45-minute interview. How is the 45-minute interview structured?

Safwan: The 45-minute interview we have with all of our potential founders is pretty straightforward. We’re trying to get to know them, understand what they build, why they built it, and their vision for how they want to scale that company. One thing we talk about or ask them about is their vision. How are you thinking about this problem? What do you think of this space? What about these competitors? How will you pivot, or how have you pivoted in the past? We’re trying to gauge what they’ve already done, what they want to do, how they can leverage our program, and how we can best help them. A lot of it is informational for us. We apply a lot of what we hear in the interview and help them if they get into the accelerator program. It’s a (casual) conversation – getting to know them, the company, and their vision.

Kieran: What advice would you give to a student founder to help them stand out during the admission process?

Safwan: I think there’s a bunch of different ways. Often, the company speaks for itself. Sometimes, the traction is excellent, and you stand out. That’s the most generic way. We’re working at a very early stage. The companies we take in are pre-seed companies. They may be pre-funding, pre-customer, and sometimes even pre-product. I think the biggest way to stand out as a founder in these sorts of interviews, not just for our accelerator program but any accelerator program, is to be enthusiastic about your company. I want to be excited about what you’re building and see you’re excited, too. I think a lot of that is how well you can excite the other person on the other side of the screen or table. The second part is how much I can learn about your company and the industry you’re working in. We’re seeing companies from various industries, and am I an expert in every industry? Of course not. So, I think a great way a founder can stand out is if they can teach me something that I didn’t know before in an easy-to-understand way. If I walk away from that interview or interaction being like, oh wow, I understand that’s a huge problem, and I get why they’re building it, then that’s super cool. If I can walk away with (those thoughts), then I think that makes for a super productive and memorable interview. I try to remember everyone I interview and make sure I study up on them.

Kieran: The program consists of this point-person structure, mentorship, and curriculum. Can you share more details of how the curriculum is structured and what is covered?

Safwan: Our program has three core tenets: mentorship, curriculum, and a point-person structure. Mentorship is leveraging our Rolodex of X investors, founders, and operators at companies with successful exits or scaled very well. We bring four to five mentors every week during our program and allow our founders to network with them and ask them any questions about overcoming specific challenges or getting general advice on something they want to do. There’s a lot more to that, but we have weekly mentorship sessions—the same thing with curriculum. We curate our own startup curriculum. So, we talk about customer discovery and how you create business models, revenue models, pricing schemes, etc. We also talk a lot about fundraising. We bring in investors from firms like Pear, Khosla Ventures, and NEA, and have our companies pitch to them to get feedback on their pitch or anything else they might need to work on. That’s a big part of the curriculum – learning how to structure the company and how to pitch it. Then, we have the point-person structure. We take two internal Free Ventures members and put some on each current batch company to help those founders with whatever they need. So, we could serve as an intern, acting co-founders, or a sounding board. Often, we find ourselves advising companies on their pitch deck and strategy if we have expertise in that space. We’re there for the founders with whatever they need. That’s our accelerator program, and we’re trying to help founders reach the (next) stage through those three avenues.

Kieran: You work with partners like Cooley, The House Fund, and AWS Activate. Can you share more about how they support the work that you’re doing?

Safwan: Yeah, so we take zero equity in the startups that we work with. That’s why we’re called Free Ventures. We don’t make any money (off of investments). So, some of the ways we make money is through sponsors. They see the value in our program and want to engage with the companies in our batch and the entire UC Berkeley entrepreneurship ecosystem. They will funnel money into our program to support our normal operations and come in for mentorship and curriculum sessions. We’ll also have one-off events for these sponsors to engage with the ecosystem, whether through general events where they want to talk about entrepreneurship or we bring them to our program to specifically advise our startups. For example, one of our partners is Cooley, a law firm that helps startups. Our contact there is super great. He comes back every semester and spends his time helping advise our companies on legal matters and how they should navigate certain regulatory things. They provide us value, and we provide them value back by exposing them to certain companies and clients they might want for their businesses.

Kieran: Are you looking to bring on more sponsors?

Safwan: Yeah, we’re always looking to bring on sponsors as long as we can provide value and vice versa. I think it’s always a fine line of, you know, how can we not only extract value from sponsors but how can we provide value to them too. Often, companies want to tap into the UC Berkeley entrepreneurship ecosystem, whether that is a potential customer base or want to learn more about the space as a whole. Whatever it may be, we’re pretty much here to do that, and we’re always open to new sponsors.

Kieran: What do you see as the biggest opportunities to improve Free Ventures in terms of how you support founders?

Safwan: Yeah, there’s a lot of room for improvement. I think our program is already really great. We’ve been around for 11 years now, since 2013. So, we’ve had a lot of time to iterate on different parts of Free Ventures, whether it’s mentorship, curriculum, or that advisory structure I talked about. So, I think we already have a great, robust program. We have a lot of great events as well. I think the way to improve it is we need better reach within the community. We need a lot more cohesiveness within the entrepreneurship community at UC Berkeley. One of the initiatives we’re working on is collaborating with other entrepreneurship organizations to create a shared system, a shared structure, where we can co-host events, have some entrepreneurship board to help make decisions on campus, and help each other out mutually. I think the big thing is that we want to integrate further within the community, work with other organizations to help them with their events and initiatives, and overall create more awareness for entrepreneurship on campus to create that accessibility. UC Berkeley is regarded as an excellent entrepreneurship school and ecosystem, and it is. But I feel like much of what happens here on campus is pretty fragmented. There is not a lot of awareness for students on how to get involved in entrepreneurship. That’s one thing that we’re trying to get better at, and we’re trying to help students out, just creating a better community around entrepreneurship and allowing everybody to get in it.

Kieran: I love that. I also went to Cal and didn’t know about the entrepreneurship or startup scenes while there. I love that you guys are trying to piece it together and make sure people are aware of the work that you’re doing.

Kieran: What percentage of student founders you work with continue on their startups after graduation?

Safwan: Yeah, quite honestly, it varies from batch to batch. We’ve had about 20 different batches now and nearly 100 portfolio companies over our 11-year time. But, on average, anywhere from 20-25% of founders will still be working on their company or pivot idea by the time they graduate or post-graduation. So, we have a pretty good success rate for it. Unfortunately, many companies do end up having to close up shop. But, we do have a pretty high rate of retainment of founders who continue building their ideas even after our program, and we’re still connected to many companies that have been in our portfolio for years now. They keep us updated on huge milestones, like, hey, they got a massive Series A or B funding, they landed that considerable customer. They come back to our program and help our current batch of founders. I think there’s great community (support) from our alumni.

– now, let’s transition to questions to help students who want to join the Free Ventures internal team –  

Kieran: Can you give an overview of the application process for internal team members?

Safwan: So, we run a lean team. We’re only ever about 7-10 people who run the accelerator on a day-to-day basis. How that structure works is we have associates who come in their first semesters here in Free Ventures. Then, on top of that, once they’ve been in the org for a bit, they move up to Director. After Director, once they’ve been leading a considerable part of Free Ventures or an initiative, they can get promoted to Managing Director. So, those are the three levels. If you apply to Free Ventures and want to join, you’d join as an Associate. The process is pretty straightforward. We have a written application and a couple of different writing prompts on there to gauge your interest level for startups and what experience level you have with startups. Do you have any previous niche interests we need to know about that could help you (support founders) or us at Free Ventures? Once that happens, we filter through candidates and select them for first-round interviews. First-round interviews are generally 30-45 minutes long. We usually ask a lot of behavioral questions or scenario questions. We’re not trying to grill anyone with a case or be overly toxic. We’re simply trying to get to know our applicants and understand their journey in entrepreneurship. Whether that was as a founder, working at a startup, or whether they are just interested in it, right? We don’t require our internal members to have startup experience, although most of us do. What we really care about is what’s your passion level. Are you seriously driven to make an impact in the entrepreneurship space on campus? Do you want to work with startups? That’s what we’re gauging in the first round. Then, after that, we move them to a final round, which consists of a presentation on how to improve our program or the entrepreneurship community in general. It’s a pretty open-ended question. But, we want to hear what people’s ideas are and what everybody says because often, we will take people on their ideas based on how they would improve our org or the community and help them do that. We also ask them some behavioral stuff, some scenario stuff. For example, let’s say a founder lost an engineer today. How would you help them with hiring again? We’re asking them real-world scenario questions to gauge how they would go about helping founders and helping them push through their biggest problems, which is what we do daily here at Free Ventures. After that final round, we generally hand out offers to 2-5 people per semester. That’s the general process – written application, first round interview, and final interview where you go over how to improve the community or org as a whole, and there will be some behavioral and scenario questions.

Kieran: As you onboard new team members to your org, how do you train them to give good advice and be helpful?

Safwan: So, when someone joins Free Ventures as an internal member, we give them a crash course and boot camp on some of these things that we do – how do you be a point-person, what is your role in advising, what value can you provide to founders, how can you help them overcome problems. Those are some of the basic things that we cover. It’s a bit abstract just because not every founder will have the same problems. But there are some commonalities right? For example, we focus on pitching because our program is geared toward helping companies get money. In our 11 years, our portfolio has raised $170 million in follow-on capital. So, as a point-person, you must help companies with their pitches, crafting their story, and instilling confidence in founders. I think that’s what being a point person at Free Ventures is all about -- helping founders create clarity in their vision. So, we teach them that, pitching, etc. Outside of that, we tell everybody at Free Ventures to use their personal experience. Like I said, most people on the Free Ventures team have worked at or founded startups. We’ve been in positions similar to these founders, and we’re able to leverage our past experiences and be like, “Hey, I’ve been through this one before or seen this before. Here’s how that person or I overcame it, and let me sit here and help you do it.” That’s what we instill in all of our new members, and even throughout the entire program, we’re always trying to get better as point people and make ourselves available. So, formal training and training along the way is ad-hoc.

Kieran: Once a student joins the Free Ventures internal team, what are some things that you can do to stand out, move up, and earn more opportunities within the org? I know you moved from Associate to Managing Director. You could talk about some things you did or excelled at that helped you move up within the org.

Safwan: Yeah, you know, Kieran, I wish there was a formula for this stuff. There, unfortunately, isn’t. Me personally, and just what I’ve seen in general is, I think it’s really about initiative, right? Ownership and initiative. Not only to make your way up in Free Ventures, but any organization is going to be how much ownership do you take in your work? Do you take pride in it? Do you go the extra mile to get things done and go above and beyond? I think that’s what we value. One thing at Free Ventures that we value a ton is, hey, you have this initiative; you wanted to do it. You have full ownership of doing it, and we’ll do everything we can to support you to get there right. Everybody in Free Ventures has their initiative that they are doing, and what we’re all about is trying to get to that point, whatever it takes. And so if you can show that passion in your work, go above and beyond, and really care about startups, that will show regardless. There’s no formula to everything, but it’s about showing ownership and taking the initiative to get things done.

Kieran: What’s the time commitment? How much time are internal team members spending on this per week?

Safwan: I want to say how much time I spend on it weekly, but it will look bad. It’s just way too much time. All jokes aside, Free Ventures is a pretty big-time commitment. I think one thing we tell everybody who wants to do this is are you sure you want to do this cause you’re going to spend a lot of time here? That’s the cool thing about Free Ventures. We do a lot of really cool work that’s very versatile. To answer your question very directly, I think I’m spending between 10-15- sometimes 20 hours per week on Free Ventures. It depends because we have events that take up 6 hours per week for me, and then there’s personal work I’m doing on the side and meetings. I’m spending a ton of time. Everyone else at Free Ventures is also spending a lot of time, probably around the 10-hour mark, but it can go up week to week. Everyone always asks, “Why do you spend so much time on this thing?” Really, it turns into a full-time job. We’re eight undergraduate students running an entire accelerator program. So, there’s a lot that goes into it. There are a lot of admin tasks on the backend, strategy right, how we learn from what we did, how we improve, and what we should do in the future. We’re hosting events all the time. We have personal initiatives that we do. I started the Free Ventures fellowship program as an Associate last year, and now it’s a staple in Free Ventures. We take in two freshman or sophomore students every year interested in entrepreneurship but don’t have a background and want to break into it. So, that’s a program I started, so managing your initiatives and working through normal operations. There’s a lot of different parts of your brain that you’re using. You may have 4-5 concurrent work streams. So, that’s the time commitment. I wish it were less, but I love it. I’m learning a lot and having fun.

Kieran: Is there anything I didn’t ask about that is important to know if you’re considering Free Venture as a student founder or someone who wants to join the internal team?

Safwan: The real high-level thing and commonality everyone cares about is passion. We want to work with passionate people. Suppose you’re a founder interested in joining an accelerator, Free Ventures, or any other accelerator. In that case, the big thing is to show that passion, why you’re building that company and that vision, and hone down on that story. I can’t harp on that enough. Story matters a ton. If you can give a compelling story, and I can leave an interview and interaction understanding who you are and learning something, that’s a huge positive and makes me want to work with you. And I’m sure vice versa as well. So, that’s the same thing for students: show that passion. If you’re trying to get into that entrepreneurship space on campus, I think Free Ventures is the perfect place. But, it could not be for you as well. I think it’s about trying to understand what you want to achieve in this community, and there’s a place and org for you as well. Regardless of your path, be super curious and optimistic, and show that energy. That’s the main thing, and it’ll motivate people around you.

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