From Jefferies to Wanelo: A 2.5-Year “Job Search”

Last Monday was my first official day working on partnerships and business development for Wanelo, a role and company about which I couldn’t be more excited. While the “recruiting process” (I hesitate to use such a corporate-sounding phrase) with Wanelo lasted just a few weeks, this new opportunity was 2.5 years in the making, as I transitioned from finance to the startup world (though I’d done a fair amount with startups as an undergrad).

While my LinkedIn profile does a solid job of showing my stops along the way and my blog and Twitter account reveal the amount of “content” I’ve produced during this period, below is a timeline that outlines my “job search” and what I learned from the last couple years.

February 2011 — September 2011: While still working at Jefferies, I cold email nearly 150 combined VCs, founders, and non-technical (i.e. biz dev) startup employees, primarily in NYC as well as Silicon Valley and Boston, seeking advice on my impending transition. This effort results in approximately 90 in-person meetings, phone calls, or email conversations.

February 2011 (my first meeting): I meet with fellow Dukie David Rodriguez, who had transitioned from consulting to working as an associate at Greycroft. He suggests going to numerous meet-ups and trying to advise or help out startups part-time. I take his advice and eventually spend late spring and summer helping out a few early stage startups in NYC that I go on to meet at various meet-ups and Ohours.

March 2011: I start my blog after a meeting with Ben Siscovick during which he stresses the importance of developing a web presence and voice alongside my Twitter account. He also mentions it’s a good way to form an opinion about another technology. I choose Tumblr for my blogging platform since it’s an NYC startup which I wanted to learn more about as a user and “content creator.”

March 2011: Chris Sacca responds to my cold email, saying he’d be more than happy to respond via email to three questions that I’d like for him to answer. I carefully choose my questions (best way to get operating experience, traditional venture funds vs. seed-oriented funds, and his thoughts on corporate VCs) and Chris gets back to me quickly with detailed answers.

May / June 2011: I somehow learn through the Twitter grapevine that Ellie Wheeler, then a 2nd year at Harvard Business School, works part-time for Chris Sacca at Lowercase Capital. Inspired after watching Chris’ epic commencement speech at the University of Minnesota, I reference a couple lines from the video and politely suggest that I take over for Ellie when I go to business school in the fall. He politely declines “hiring me” but says he may have some projects I could work on.

June 2011: Chris proposes an “informal collaboration”: start a Google doc that includes 20 or so “momentum-driven” startups that are flying under the radar and we can go back-and-forth revising the list given our respective justifications. 10 days later, I finish the list.

Summer 2011: After my last day of work at Jefferies on June 30th and returning home to Philly, I make trips nearly every week to NYC to meet with people and the startups I am helping out.

I spend a couple months doing some work for DreamIt Ventures after initially getting introduced to David Bookspan and, subsequently, Kerry Rupp.

I follow up periodically with Chris to get his thoughts on the startup list and see if he needs any other help.

I have a call with Paul Lee, a partner at Lightbank, after sending him a cold email. He mentions that Jessica Kim, founder and CEO of BabbaCo, is moving from Chicago to Boston, and I may be able to help out while I’m at school. He introduces me to Jessica shortly thereafter.

August 2011: I move to Boston to start business school and try to meet as many people in the Boston startup scene as possible.

October 2011: Chris emails me out of the blue asking if I have time to work on a project for a portfolio company. I’m in the midst of midterms, so of course I have time. A few days later we get on a call to discuss the project. Rather than doing reference checks and a formal interview, Chris mentions how he looked at my Tweets and blog, and that’s enough for him. Depending on how this initial project goes, we could discuss a more formal role.

October — December 2011: I work on this project alongside my friend Peter Boyce, who also had gotten to know Chris. In December we get on a call with Chris and the company to present the model I built and the deck that we put together.

January 2012: During my first trip to Silicon Valley, I get an email from Chris saying that the company and he liked the work I did, and he’d like to have me work remotely as an associate for Lowercase (get a Lowercase email address, go to demo days, do due diligence, etc.).

January — May 2012: I spend the remainder of the school year working on a handful of smaller projects for Lowercase.

February — May 2012: I work on a couple business development-related projects for BabbaCo after Jessica and part of the team gets settled in Boston.

March 2012: During spring break, I go to SXSW for the first time and meet Sahil Lavingia, founder and CEO of Gumroad. I also go to SF to meet some more people and end up chatting with Sahil again. We discuss the possibility of having me intern at Gumroad.

I conclude my spring break visiting friends in LA, but not before Chris sees a Tweet about my being there. He emails me proposing that we meet in Manhattan Beach since we’ve never met in person before. I take an Uber (what else) down from Westwood and meet Chris in person for the first and, to this day, only time. I spend 2 hours at his house, and he tells me about his time at Google, starting Lowercase, and life in Silicon Valley. We also talk about my options for how I should spend my summer in between years at business school.

April — October 2012: I start working remotely for Gumroad from Boston, spend the summer working with the team full-time out of Sahil’s apartment in SF, and continue to work remotely again during the first couple months of school.

November 2012: While at home for Thanksgiving, I meet with Josh Kopelman of First Round Capital, an investor in Gumroad, at their new office by UPenn to get advice as I think about what I should do post-graduation.

February — May 2013: I work part-time doing business development for PICT, a Lowercase portfolio company, after getting introduced by Chris to Brent Locks, PICT’s co-founder and CEO. Working with PICT helps me grow more familiar with the retail space.

June 27, 2013: I email Josh asking if he has time to chat while I’m at home in Philly and to see if he’d be able to intro me to Deena Varshavskaya, Wanelo’s founder and CEO.

June 28, 2013: Deena emails me referencing Josh.

July 8, 2013: I meet with Josh in Philly.

July 9, 2013: I have a 1-hour call with Deena.

July 11, 2013: I meet with Deena and Sean Flannagan, Wanelo’s VP of Product, at the company’s old office in SF.

July 12, 2013: Deena proposes I do a trial run working with the Wanelo team to see if it’s a good fit.

July 25 — August 2, 2013: I work with the Wanelo team on a couple business development projects.

August 2, 2013: I receive an offer to join the team full-time and do so beginning August 5.

August 13, 2013 (tomorrow): I will fly to SF to re-join Wanelo at the office and move to the west coast.


One of the most amazing and refreshing aspects of the startup ecosystem is the “pay it forward” mentality and people’s willingness to be helpful. I was and still am a grateful beneficiary of this aspect of the startup community and have tried my best to do the same for others. A myriad of people whom weren’t included above were also instrumental in helping me during the last couple years, and I owe them all a debt of gratitude.

If nothing else, my biggest takeaway from this entire process is that you make your own luck. Constantly doing your best to be helpful and add value goes a long way and should give you an opportunity to succeed. And while in hindsight, I could draw a line from working with Chris and Lowercase, to Sahil and Gumroad, to Josh and First Round, to Deena and Wanelo, the transition wasn’t quite that seamless and direct. There were many factors (both people and events) — too many to recount in the timeline above — that contributed to the successful completion of my job search.