The Lucky Chairs

John Gallaugher
5 min readSep 8, 2023


Two chairs in my office. One has a bottle of “Tres Comas” tequilla on it.

When students drop by my office to discuss their entrepreneurship interests, career goals and technical projects I often point out that they’re sitting in “The Lucky Chairs.” In the over quarter century that I’ve been teaching, I’ve had the good fortune to have been sought out by many undergraduate students who would go on to build substantive businesses. These office chairs are unremarkable, but they’ve at some point held some of our most remarkable students.

Nick Rellas, Justin Robinson, and Spencer Frazier sat in my office pitching an app that I was initially skeptical of — after all, what undergrads haven’t thought of pressing a button and having beer delivered. So much for my skepticism — the business they built, Drizly, would later be bought by Uber for over $1 billion. They weren’t the only former students who would garner unicorn valuations. Former student Andrew Boni founded tech marketing standout Iterable, former student Andrew Chang would help build crypto firm Paxos as COO, and Brooke Brown was one of the first five employees at Rent the Runway and would serve as the firm’s Chief Product Officer. There was also Bill Clerico, with classmate Rich Aberman, who sat in the chairs when they shared the idea for WePay, a Y-Combinator alum, and a firm JPMorgan Chase decided to buy for a reported $400 million.

Many founders also served as Teaching Assistants for my courses. One of the first TAs in my Swift app building class was Branick Weix — an alum of three of my classes and who I’d been chatting with since before he enrolled. Branick sold his real estate photography platform, Aryeo, to Zillow earlier this summer. Swift TA Linda Shad Chen just finished a stint in A16Z’s game accelerator where she and her cofounder grew the audience for their mental health game, Voidpet. TA Matt Giovanniello has built a thriving firm, Frenelytics, focused on supporting people with cognitive impairments, and Jimmy McDermott continued to build his platform for service learning, Transeo, even while serving as a TA for the apps class.

Some former students were also coached by our TA entrepreneurs — Swift student Kelsey Bishop went on to found Candor, and Swifter Lurein Perera founded two firms including donation startup, GiveCard. If you’ve browsed an online menu, you might have used a site created by Ameet Kallarackal’s Fisherman. Many of our entrepreneurs provided their own supportive cohort, like the three separate firms adjacent in TechStars Boston: Tom Coburn, Chase McAlesse, and Jonathan LaCoste who founded tech marketing firm, Jebbit; Miguel Galvez and Deck Sorensen who founded materials firm NBD Nano; and Brett Beaulieu-Jones and Alex LoVerde, who turned SyncOnSet into a tool so important to the motion picture industry that they won a Technical Emmy Award. Some who’ve sat in “The Chairs” have gone on to distinguish themselves as investors. Meagan Loyst was a standout at Lerer Hippeau and founded GenZ VCs, and Josh Coyne who’s a Partner at Kleiner Perkins, come immediately to mind. And there are many others who have gone on to distinguish themselves as engineers and managers in leading tech firms: Apple, Amazon, Google, and Meta, among them; or who went on to grad school at the most elite level, including Harvard, Stanford, MIT, and Oxford.

One of the most rewarding things about working with so many talented students is that they often come back as alumni, meeting with and inspiring my current students. I’m a bit squeamish that I might sound like Harry Potter’s Prof. Slughorn, listing the achievements of former students, but I do hope the list inspires the current and future generations of students, especially those who try their hand at entrepreneurship.

Oftentimes when students hear about “The Chairs”, they stop by to ask me for introductions. This is actually a terrible tactic in early meetings and one that’s often a quick turnoff. Most founders and investors are profoundly busy, so if you’re going to approach them, you ought to have something solid to show. Related to this, one thing that often distinguishes success is the work that a student has put into their idea. I can often tell a student will struggle as an entrepreneur if the first thing they want to show me is a “pitch deck.” The students who are most successful tend to show me the products that they are building. That’s advice you’ll hear from the best tech leaders, as well. For example, in one of my courses, I used to bring students to Silicon Valley to meet with CEOs, founders, investors, and other tech industry managers. In this course students met with the late Bill Campbell, a legend in tech circles, known as “The Secret Coach” and “The Trillion Dollar Coach.” Campbell has advised scores of luminaries, including Steve Jobs, Jeff Bezos, Eric Schmidt, and Marc Andreessen. In every meeting we’d have with Bill, he’d lean in to my students and with his gravelly voice he’d say “Marketing forgot its first name — it’s ‘Product’” (at Apple, where Bill previously worked and was Chair of the Board, the firm’s head marketer held the title SVP of Worldwide Product Marketing. For years this was Boston College alumnus Phil Schiller — another brilliant and kind exec who regularly spoke with my students). So if I have advice for students, it’s to use your collegiate startup time focusing relentlessly on building product. Do note that very few students have the perfect product-market fit out of the gate. Most entrepreneurs have to pivot their idea — often multiple times. But without a product, very few will take you seriously — not potential co-founders or hires, not customers, not investors. And once you have a product with traction, you don’t need me for an intro — you’ve got something tangible to show that you can get real feedback on.

Those chairs are lucky, but they’re lucky to have been sat in by students with that secret set of attributes essential for success — talent and tenacity. The path an entrepreneur travels is full of struggle, pain, and disappointment, but for some, also the incredible reward of having built something that provides jobs and that others find useful. If you’re around Fulton 460c, you’re welcome to drop by and sit in “The Lucky Chairs,” but that won’t be your ticket to success. The real goal is to build something great. Keep Hacking!

Prof. John Gallaugher teaches technology and business in the Carroll School of Management at Boston College. Prof. Gallaugher is an Apple Distinguished Educator. His award winning textbook on technology and business has been used in courses at over 450 universities. His course lectures on building apps in SwiftUI and in building hardware projects in CircuitPython are available free to all via YouTube. You’ll also find additional educational material, including course slides and exercises, at If you use his material, let him know! But please don’t write him asking to debug your code.



John Gallaugher

Boston College Prof. Tech/Business. Advises student entrepreneurs, TechTreks (S.Valley/SEA/BOS/NY,/Ghana). Book