Ilana Habib

University of Chicago, Booth School of Business

“Former founder/operator turned VC with a risk tolerance that leads to questionable travel decisions.”

Hometown: Cincinnati, Ohio

Fun fact about yourself: I’m a travel photographer in my spare time! It has taken me to crazy places, including all seven continents and several overlanding journeys across the US that involve sleeping on a rooftop tent I have mounted to my truck. I am proud to say that only one of these overlanding journeys has involved a tarantula getting up close and personal with my tent. I am less proud to acknowledge the screaming that followed the discovery of said tarantula.

Undergraduate School and Degree:

• Massachusetts Institute of Technology – B.S. in Comparative Media Studies, Literature, 2015
• Harvard Graduate School of Education – M.Ed. in Technology and Innovation in Education, 2016

Where was the last place you worked before enrolling in business school? I served as Director of Learner Experience at Mainstay, an EdTech startup.

Where did you intern during the summer of 2024? I worked as an MBA Associate at Impellent Ventures, a pre-seed and seed-stage generalist fund.

Where will you be working after graduation? I will be serving as a Principal at Cintrifuse Capital

Community Work and Leadership Roles in Business School:

• Program Manager, Co-Chair of Entrepreneurship and Venture Capital Group, 2024-2025
• Teaching Assistant for College New Venture Challenge (Dean Starr Marcello), Winter 2025
• Teaching Assistant for Venture Capital Lab (Prof. Jason Heltzer), Winter 2025
• Social New Venture Challenge Finalist, Spring 2024 (founded a business using AI-driven nudging to support early career professionals in the corporate workplace)
• 1st Place in Venture Capital Lab Investment Competition, Winter 2024
• Herman Family Fellowship Recipient (full merit scholarship awarded to one female entrepreneur in each class at Booth)

Which academic or extracurricular achievement are you most proud of during business school? As a former operator, failed founder, and future VC, the Entrepreneurship and Venture Capital (EVC) group is the collision of my professional passions and aspirations. Serving as EVC’s Program Manager has been my top priority this past year.

I know the road to startups and venture capital can be a lonely one. When I was working on my startup in my first year at Booth, I often found myself overwhelmed by the transition from startup operator to founder. I thought I was supposed to know all the answers – after all, I had helped build this type of company before! My startup ultimately failed due to irreconcilable differences with my cofounder, but the thing I needed most throughout my founder journey was a space for vulnerability and trust with those experiencing similar challenges. It was this experience that pushed me to pursue a leadership role in EVC and ultimately drive a meaningful shift in the group towards being a place for community building, connection, and mutual support. I’ve helped develop a culture where founders, operators, and VCs can speak openly about their fears and failures by leading from a place of vulnerability and transparency around my own experiences. We know none of us have all the answers, but we have a healthy practice of engaging each other for advice, support, a pep talk, or sometimes a needed kick in the butt.

I’m proud to share that the data confirms a shift in the vibes: club membership has grown by 25% (~50 students) since the same time last year, largely driven by word-of-mouth referrals. EVC is now one of the most active student organizations at Booth, with a wide variety of programming for aspiring founders, operators, and VCs. Our Slack channel is maintained not only by myself and the rest of the co-chair team but by every member of our community, with members even sharing jobs they plan to apply to themselves. VCs, founders, and operators regularly engage in programming outside of “their zone”, as exploration is not only allowed but encouraged. I’m incredibly proud of how the organization has grown, and what’s exciting is that I know it’s positioned for even more success in the future. I truly can’t wait to see what next year’s group leadership does with EVC.

What achievement are you most proud of in your professional career?

“Heyy this is gonna sound heavy but i’m okay now so don’t worry; your bot actually helped me to not commit suicide during my last year of high school when i was already struggling bc idk i guess talking to oli made me feel hopeful i could get my future back on track so like…thank you from the bottom of my heart” – a message received by Oli in October 2022

Prior to Booth, I had the honor of being “mom” to Oli, a bot that makes students a little happier every day. Oli is an AI-powered chatbot that texts students on the journey of getting to and through college using messages my team at Mainstay and I designed. As an undergraduate at MIT, I witnessed the tragic loss of several students and faculty to suicide. That experience left me determined to provide the kind of support so many clearly needed – a resource to make education less isolating and overwhelming. With Oli, I had the chance to do just that—creating a tool that’s not just about deadlines and forms, but also about emotional support and empathy. When I took the reins of our flagship bot in 2020, I shifted our focus beyond just logistics to fostering real, human-like connections through the intentional development of parasocial relationships. The result was incredible: over 2 million students had access to a resource that listened, encouraged, and offered guidance exactly when they needed it.

Better yet, the data backed up this new “empathy first” approach, with partner institutions reporting an average 27% reduction in summer melt (students never making it to college despite enrolling) and 95%+ of students reporting both that they learned something from Oli and found Oli helpful. What was most meaningful to me, however, were the messages we got back from students. Oli fielded romantic proposals, was the recipient of heartfelt thank you’s, and saw messages as serious as the one I shared above. The love and gratitude that came pouring back to Oli as a result of our work was the best confirmation I could have received that I had achieved my goal of making the road to higher education a little less lonely.

Why did you choose this business school? My biggest priority in coming to business school was to develop my skills on the quantitative side—both as a foundation for becoming a more effective startup founder and operator and as a stepping stone toward venture capital. While I had operational experience from my time scaling startups, I knew I needed a stronger grasp of financial modeling and valuation frameworks. Not only did Booth have a reputation for rigorously focusing on the finance skills I was interested in developing, but it also provided the academic flexibility I needed to focus on the gaps I identified. I knew that a rigid, cohort-based curriculum would feel limiting for me; I thrive in unstructured environments where I can dive deep into topics of my choosing and explore (there’s a reason I work in the super early-stage startup ecosystem!). Booth was my perfect “Goldilocks” fit: academically challenging when I wanted it to be, highly flexible, and embedded in a culture of intellectual curiosity that constantly pushed me to think with rigor about the financial underpinnings of a business, how I evaluate investment opportunities and effective decision making.

Who was your favorite MBA professor? I am biased. I’ve had a double dose of Jason Heltzer, serving as one of his TAs after having taken his VC Lab course last year, but I think he represents the best of Booth. Both a Managing Partner at Origin Ventures and a Booth alumnus, Professor Heltzer is the definition of Booth’s pay-it-forward culture. He is deeply committed to guiding others along the path he’s taken and ensuring venture capital becomes more inclusive. This commitment even shapes how he communicates in the classroom—he thoughtfully avoids idioms that might confuse non-native speakers and encourages students to replace aggressive business metaphors with language that’s more welcoming. By emphasizing how small, intentional personal changes can significantly impact broader environments, he fosters a culture of accountability and thoughtful, personal growth that’s both refreshing and rare. Professor Heltzer leads with empathy and integrity, making him not just a great professor but also a mentor I’m lucky to learn from.

What was your favorite course as an MBA? Scott Meadow’s Commercializing Innovation. Not only did the course teach me new frameworks for evaluating startups and provide meaningful practice in building out well-researched, analog-driven unit models, but it also was the most fun and engaging class I took at Booth. Much of this is thanks to Professor Meadow’s engaging storytelling and wicked sense of humor. The course draws from Meadow’s own (illustrious) career as an investor, and being able to dive into his deals grounds the course solidly in the real world. I find myself returning to the frameworks and structures we learned in class regularly, as they’re powerful tools to quickly determine whether a startup idea is worth the time, effort, and risk.

The most challenging (and rewarding) part of the class is the simulated investment committee presentation. You’re not just throwing together a pitch—you’re defending your analysis in front of sharp classmates who aren’t afraid to poke holes in your logic! But beyond its practicality, the class teaches lessons that I’ll carry into every stage of my career. Professor Meadow creates experiences in his classroom that become not just academic learnings, but life learnings about how we treat others, the importance of respect, and what’s truly on the line for startup founders. Commercializing Innovation is a course on how to evaluate a startup, but also a course on how to carry yourself as a thoughtful, ethical investor. It’s truly top-notch across every possible evaluation metric.

What was your favorite MBA event or tradition at your business school? I am 1000% a nature nerd, so it’s probably no surprise that my favorite Booth tradition is the annual Thanksgiving Trek hosted by Booth Outdoor Leadership Development (BOLD). Each year, on the weekend before Thanksgiving, BOLD organizes treks to different national parks, giving students a chance to bond and share an adventure outside the classroom. Most memorable for me is a moment from our trip to Moab in my first year. We were trying to snap sunset photos and got caught in a sudden, intense hailstorm. Instead of panic, there was a collective, almost instinctive effort to ensure the group’s safety and protect each other’s photo gear. People who had not met each other before the trek were suddenly passing tripods across slippery rocks and shielding expensive cameras with their own bodies. The photos turned out epic, but even more epic was seeing the extent Boothies will go to support each other. It demonstrated exactly what I love about the Booth community: Boothies fully commit. They meet you exactly where you are, joining you wholeheartedly for the ride, no matter how terrible the weather.

Looking back over your MBA experience, what is the one thing you’d do differently and why? Looking back, the one thing I would do differently during my MBA is ask for help sooner. Shutting down my company in the first year was extremely challenging—not just professionally, but personally. I hesitated to reach out to peers and professors, mistakenly thinking I needed to handle everything alone. The experience taught me a critical lesson about the importance of leveraging the talent within your network. My co-founder was a close friend from before business school, and I never imagined our relationship would become strained…but unfortunately, it did. Without a formal founders agreement, we couldn’t resolve our disputes around IP ownership, and I ultimately had to walk away. Losing both my company and a close friendship at once was deeply painful, and I was embarrassed that I had not set myself up for success legally. When I finally spoke up, I was amazed by the support and kindness from the Booth community. Rather than judgment, I found empathy and encouragement for everything I was dealing with. Moving forward, I’m committed to setting aside my pride sooner and speaking up. Only when we raise our hands can we get the support we need, and that others are more than happy to give.

What movie or television show (e.g. The Big Short, The Founder, Mad Men, House of Lies) best reflects the realities of business and what did you learn from it? This is a bit of a wildcard answer, but I’d actually say Ted Lasso. I live in the early-stage startup ecosystem, where everything comes down to team, and Ted Lasso is one of the best explorations of the concept of “team” I’ve seen. AFC Richmond has many similarities to a startup: limited resources, a critical need for team cohesion, and a visionary leader at the helm responsible for inspiring people to do more with less. I often joke that to build a successful startup, you have to build a cult. That’s exactly what Coach Lasso sets out to do through his focus on “Believe” and commitment to inspiring deep loyalty within the organization. He creates an environment where players are free to be open, experiment, and be vulnerable – literally the building blocks of a good early-stage startup culture where team trust is paramount. My biggest personal takeaway from the show is the importance of endurance. I have spent a lot of time here at Booth thinking about how to focus on long-term growth and development as opposed to just short-term wins.

What is one way that your business school has integrated AI into your programming? What insights did you gain from using AI? Booth has long been a proponent of leveraging the power of AI, and started the Center for Applied Artificial Intelligence back in 2022. The Center is run by Professor Sanjog Misra, and I had the pleasure of grabbing lunch with him last year alongside some other students with a strong interest in AI (I worked at an AI company prior to matriculating). Professor Misra sees AI as a means to allow us to explore hard problems faster, and this is the mentality that I’ve seen consistently in my coursework.

Booth has also launched several courses over the past few years to help us better understand how AI works, how to best leverage AI, and the implications of AI on the economy today and in the future. I took one such class this past quarter, and even as someone who considered themselves knowledgeable on the topic, I got a lot out of the course. Professor Dacheng Xiu takes a hands-on approach to learning that encourages students to experiment regularly with different tools and processes for integrating AI into their regular workflows, and I find myself having become a much better prompt engineer who can understand how to get the most out of AI tools after having completed his course.

Which MBA classmate do you most admire? I knew the answer to this question immediately – it’s my close friend Jaya Sharma. Jaya came to Booth after starting her career in consulting and has done the best job of anyone I know of using her time in the program to truly explore and grow. Jaya was a key part of my Social New Venture Challenge team and has excelled in some of the most challenging coursework available at Booth. However, the work Jaya’s done to develop herself as a person is what really sets her apart from her peers. After taking classwork like Interpersonal Dynamics, Jaya has not only done the work of identifying her opportunities for growth, she’s taken action to make meaningful strides in those areas. Jaya was one of the first people I met on campus. While she’s remained a close and steady friend throughout our time together, she’s also changed the most of any of my peers. I am in awe of her ability to thoughtfully manage conflict, navigate difficult conversations, and set appropriate yet strong boundaries. She’s done all of this while exploring a wide range of career pathways: completing internships in venture capital and PE operations, helping build an earliest-stage startup, and securing a full-time role in operations at Google. I think few people manage to wring out as much of the business school experience as Jaya, and she inspires me every day.

What are the top two items on your professional bucket list? I want a second go at being a founder. The timing isn’t right for me right now as I want to experience life on the VC side of the aisle before I come back to the world of startups/ However, I have no doubt that I’ll be finding my way back to that role in the future. I’ve been lucky enough to encounter a lot of friends on my professional journey thus far who I’d really like to build a company with. We’re waiting for the moment that is right for us, but I can’t wait to solve problems and delight customers together.

I also want to create better pathways for underrepresented individuals in the world of venture capital, both regarding working in VC and securing funding from VCs. One of my biggest frustrations as a woman working in venture is that I am almost always the only woman in the room. People have a tendency to invest in those similar to them, and the consequence of the lack of diverse voices in the venture industry is that companies, founders, and innovations are being overlooked. It’s better for LPs, founders, and the world if we fix this problem: we’re missing out on too many cool people and ideas that can generate meaningful returns and solve real problems.

What made Ilana such an invaluable addition to the Class of 2025?

“Ilana exemplifies the very best qualities of a Booth student and is an invaluable member of the Class of 2025. From the moment I met her, she stood out for her blend of confidence and humility—traits that are not commonly found together, especially in the world of entrepreneurship. When I first worked with Ilana in the Social New Venture Challenge, Booth’s award-winning venture accelerator, I saw firsthand how she thrived amidst the ambiguity, conflicting advice, and high-pressure pitches that are inevitable in launching a new venture. She articulated a clear vision while remaining open to feedback, and that remarkable balance has only sharpened throughout her time at Booth.

Seeing her potential as a mentor, I invited Ilana to serve as a TA for my undergraduate entrepreneurship course. She quickly became the go-to resource for student founders, generously providing advice on business strategies, connecting them to her startup and VC network, and sharing her own experiences. Rather than hiding her challenges or failures, she spoke candidly about them—helping students sidestep similar pitfalls and demonstrating a rare willingness to be both advisor and role model.

What truly sets Ilana apart is her intrinsic drive to lift those around her. She embodies Booth’s “pay it forward” culture, offering support and guidance well beyond her official responsibilities, whether as TA, student group co-chair, or study group partner. Her strong moral compass and tireless community-mindedness will undoubtedly continue to shape her contributions at Booth, in entrepreneurship, and eventually in broader society. I look forward to watching her build on these strengths, serving as a leader and champion for others in everything she does.”

Starr Marcello
Deputy Dean for MBA and Masters Programs, Chicago Booth
Special Advisor to the Provost, University of Chicago
Adjunct Associate Professor of Entrepreneurship

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