Unwritten rules for recruiting employees into your startup. We were already 43 minutes into a 30 minute call, so now I was late. I hate being late. Exasperated and flummoxed, I noted the time and blurted two suggestions: “First. Nut Up. You’re going to be working with an amazing Data Scientist who can serve as your mentor, in a company you seem to really like, in a field you’re fascinated by, with a team experienced at creating startups that lead to value creation.” I paused to let that distill. “Second, I am a sales and M&A guy. , so… I refuse to negotiate against myself You are going to have to tell me exactly what you are asking for.” The air on the other end of the line went cold. You could literally feel the chill. The relationship we’d been developing through an engaging, transparent, mutually-respectful conversation evaporated in milliseconds. Silence. Then a murmur, Ok, bye then. “Wait,” I offered. “Where are we?” “I feel like I’m now on the spot. I’ll get back to you.” Let’s rewind the tape a bit. Recruiting is never an easy task, especially if your bar is high in a field that requires ultra specialized skills. A few months ago, the team at Flipside decided to add a Data Scientist to our squad; the right individual would be paired with cofounder Eric Stone — one of the I’ve ever had the pleasure to work with. Crypto most magnificent Data Scientists We kicked the process off in earnest. We interviewed dozens of candidates; we kissed a lot of frogs; we spent countless hours coordinating, interviewing, discussing. Twice we found individuals we thought would be perfect fits. In the first case, the candidate showed up 15 minutes late to our first meeting without even apologizing, but then we were absolutely blown away. She was thoughtful, experienced, and engaged. Then, things got weird. She cancelled a few meetings at the very last minute for family issues in another state; then, well, we found some stuff online that wasn’t so becoming. Instead of offering to reschedule, we politely offered her a way to “press pause” due to the family stuff — and she agreed. Months of work, and still no resource. We were beyond disappointed. Then we met another candidate who was quirky and brilliant. We gave him the exercise we provide to candidates and…damn, he flubbed it. Argh. We were honest. We provided a treasure trove of feedback, and — whaddya know — he responded incredibly well. He showed true ability to sponge our information and expressed how excited he was to take his skills to a new level. Then, suddenly, he withdrew his candidacy. He offered something about wanting more flexibility in a remote role — but was super critical of a typo on our website (for real). We were crushed. Another month of work down the drain. “Hire slow, fire fast,” is what they say. What they don’t say is the only way to do that is to beat off desperation with a big friggin’ stick. Desperation’s wicked stick Then we met our most recent candidate. So…shall we call him ? Mr. Nut Up He was new to Boston, and after some time in the military, spent a few years at a global corporation comprised of hundreds of thousands of employees. After passing all of our phone screens, he completely crushed the exercise. He said it took him 20–40 hours. An oddly broad range (especially for a data scientist) but this didn’t seem a show stopper. He came in for a few hours of interviews; the chemistry was obvious. The fit seemed…perfect. he had an offer in hand from another company and But here was the rub: had to determine if he was going to take that in a few days. Together, we agreed to shortcut the process: he came in for another whiteboard session, and we concurrently arranged immediate reference checks. It felt rushed, frenetic. We couldn’t possibly get to know each other in such a short time, but…the clock was ticking. Eventually, we determined he was worthy of pursuit. We outlined a cash and option package (larger than his other offer) and enthusiastically told him if he wanted the job, it was his to have. The next day, an email. Subject: Accepting the Flipside Crypto Offer. “After much deliberation, I have decided to choose Flipside Crypto. Know that the decision was not easy. However I recognize a rare opportunity when I see one. But that alone was not enough to sway me. I was impressed by the outstanding team and the character of its members. I consider it an honor to be part of Flipside Crypto and will do my best going forward.” Thrilled, we fired off an official offer. He responded enthusiastically, but asked if I would mind helping him understand how equity and options worked in startups. Easy peasy. The next morning, we hopped on the phone. He started by asking about the vesting structure, but then quickly to an outline of the option package’s potential value based solely on our last exit ( ). All fair and valid things to probe — and the conversation was fluid and upbeat. Smarterer @ $75M But the questions continued. (Absolutely, when we hit milestones.) (Yes, actually maybe a bit on the higher side.) (Yes, that often happens.) Would there be additional grants? Was his amount of shares in line with others? Would there be acceleration if we were acquired? After 20 minutes, the questions became less clear, less direct, less obvious. We began going in circles. He stammered and paused. I kept asking him what he actually wanted. I hinted that maybe it was a larger option grant? He kept reiterating the same questions. He hemmed and hawed. He said he was trying to compare his option package to a 401k he might receive at a larger company. More circles. More pauses. Then, I broke. I couldn’t handle the indecisiveness. The lack of clarity. I couldn’t handle what felt like a fishing expedition in pea soup-like fog. My brain flashed “ ,” a phrase I first heard uttered by Woody Harrelson in Zombieland. Nut Up Then I said it out loud. Zombieland’s infamous quote uttered by Woody Harrelson An hour later, an email: “You have a great company and will no doubt find the talent you need to succeed. This truly was a difficult decision for me, but at the end of the day, I don’t feel like this is the place for me. I apologize for my lack of certainty and wish you the best in your search.” I’ve hired hundreds of employees over the years and it never gets easy. You can practice, you can study, you can learn. But you will always be a student. Having reflected on this recent situation, I’m reminded of a number of important lessons for any hiring process: There are always time constraints, always reasons to rush — and rushing often leads to mis-hires, or a poorly constructed relationship. Damn it, never (ever) cut corners. One reference noted the candidate “could be stubborn, especially when it came to communicating with the business side of organizations.” A red flag. In this case, overlooked and ignored because we were rushing. Reference checks are not box checks. In a post mortem (after declining the offer), the candidate later admitted he, “started second guessing himself the minute he sent the email accepting the offer.” Never underestimate people’s ability to fool themselves. If someone isn’t able to frame their needs, you’ll always be a step away from the truth. Hire communicators. I’ve had new hires fail to show up for the first day of work. No matter how sure you are, there are always surprises. A deal isn’t done until it’s done. Finally, That’s a new one, I guess. don’t tell a candidate to “nut up”. Turns out class is still in session.

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