How This Female Founder Secured An Unexpected Seed Round
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From Student Housing Startup to Africa’s Largest Platform with DigsConnect's Alexandria Procter
This week, I sit down with Alexandria Proctor who shares her journey of building Africa's largest housing platform, securing a surprising seed round, and transitioning from CEO to CTO, to authoring a book.
Here's what you're in for:
ABOUT ALEXANDRIA PROCTER
Alexandria Procter, founder of DigsConnect, Africa's largest student housing marketplace, which she launched at age 24 while studying at the University of Cape Town. From building the initial MVP using Python and JavaScript, she's grown the platform to connect over 150,000 landlords and tenants across 400 cities worldwide, listing more than 1.3 million beds and generating tens of millions in lease value.
Beyond entrepreneurship, she's made significant impacts in various spheres - from being appointed by President Ramaphosa as the youngest director of the National Youth Development Agency, where she successfully led the One Million for Democracy initiative, to founding House of Pharos, an SDG-aligned venture capital fund. Her achievements include becoming a published author with her national bestseller "Upstart" (2024), and establishing The Aviation Club, where she writes about tech, startups, and development economics.
Connect with Alexandria on:
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Let's Connect:
Guest: Alexandria Procter | Host: Jason Kirby
Jason Kirby: Hey everyone, welcome back to fundraising demystified. Today... digs connect out of South Africa. Welcome to the show today.
Alexandria Procter: Thank you, thank you Jason, it is lovely to see you again, it's good to be here.
Jason Kirby: No, it's great. We met at lunch not too long ago. I was fasc...ust give the audience a little bit of context to who you are.
Alexandria Procter: So I started my company when I was a student at the Universi... scene. It's almost like I would say like almost like viable.
Alexandria Procter: career path thing, a startup founder. So how it all happened...mpus, but like there's no plan B. Like if you're not in res,
Alexandria Procter: like you're on your own in a way. the university solution to thi...gs in South Africa means like a commune, like a student commune.
Alexandria Procter: It's kind of used also in lot of like the Commonwealth countries...d it. And I was like, wait, what are you launching digs connect?
Alexandria Procter: And I think no, no, no, no, it's DIGS Connect. And yeah, exactly...nwide protests called Pizza 4 and there was one called Shackful.
Jason Kirby: Keep it PG with digs, D-I-G.
Alexandria Procter: And that was focused on the fact that there was no student housi...hat support. And these are the most vulnerable students who need the most secure accommodation, good living, good living ex...redible because they work in a very difficult circumstances. And most Africans have been going out and buying flats and houses. And even we have a burgeoning PBSA, which is purposeful student accommodation sector. And these landlords have mortgages to pay, first of the month, the banks taking their money, whether you like it or not. They’ve got to get tenants in paying that rent. And so there really was, you know, from both sides, this need to really connect. But back then, I didn’t know it was… I wasn’t thinking about market dynamics. I wasn’t thinking about the burgeoning PBSA sector. I was just like, “This is my responsibility, I need to sort it out.”
Jason Kirby: And what were some of those early traction points that told you this was bigger than a student side project?
Alexandria Procter: So when we launched in January 2018, it just blew up. Within two weeks we had over 1,000 listings. Students were sharing it everywhere. We were on all the Facebook meme pages, WhatsApp groups, posters around campus. It was crazy. Landlords were coming into my office in student government asking to be listed. We had this insane pull from the market immediately.
Jason Kirby: So no monetisation at the start? Just usage?
Alexandria Procter: Exactly, no business model. But landlords started saying, “Hey, can I pay you to keep my listing at the top?” And that’s when it clicked. I remember the first payment—50 rand. It felt huge. It was like, wow, I created value and someone is willing to pay for it. That’s the essence of business. And that’s how monetisation started, accidentally.
Jason Kirby: And then fundraising followed?
Alexandria Procter: Yeah, we weren’t planning on raising. But demand and traction were so strong. We set out to raise R2m and ended up closing R12m, which was about six times what we thought. That was the largest student housing seed round in South Africa at the time. The investors were incredible, backing us not just with money but also with networks and guidance.
Jason Kirby: What did you use that capital for?
Alexandria Procter: Team, product, and expansion. We went from Cape Town to nationwide, covering over 400 cities and towns. Building liquidity in both sides of the marketplace was key—getting landlords verified and onboarding students in volume.
Jason Kirby: How did you verify landlords and ensure trust on the platform?
Alexandria Procter: We built systems to screen landlords and properties. Students needed safe housing, and government funding meant universities had to trust where the money went. Verification became central to the product—we were solving for trust, not just listings.
Jason Kirby: Talent—what did hiring look like in South Africa?
Alexandria Procter: Cape Town is such an undiscovered gem. English-speaking, favorable time zone, high talent density. Support roles cost ~R10k/month; mid-level engineers ~R60k/month. Compared to the US, it’s 4–5× cheaper. Office space and utilities are affordable too.
Jason Kirby: That’s powerful arbitrage. So you’re scaling, raising, and then—tell me about stepping down as CEO.
Alexandria Procter: It was tough but right. The company’s needs evolved; my skill set didn’t match the next phase. Humility matters—you’re stewarding other people’s capital. I stayed on the board. Around then, I signed a book deal for Upstart and began policy work with national bodies, G20, BRICS, COP. Writing had always been part of me, and it became the next chapter.
Jason Kirby: And now you’ve started a fund?
Alexandria Procter: Yes, I began by writing angel-style checks while structuring the fund. Build momentum while building the vehicle. My vision is successive funds with theses around big human challenges. Long horizon, high conviction.
Jason Kirby: Closing advice for founders?
Alexandria Procter: One: don’t forsake health; pace yourself. Two: cringe-max—ship even if it’s embarrassing. Three: destiny-max—the story you tell yourself defines outcomes. Keep pushing.
Jason Kirby: Where can people find you?
Alexandria Procter: On my website and socials. My book Upstart is available in SA bookstores and online globally.