I ask every person I interview the same question – “if you were scrolling on Indeed and the job of a lifetime popped off the screen – what would that look like to you?”
I usually follow up with, “And if you say this position, you won’t get it.” to lighten the mood, but I’ve found it’s a really great way to get a candidate talking honestly about themselves.
If you asked me that question five years ago I would have said: “I was an econ major, but hated the classes. I really like business finance and the stock market, but I really like startups. I don’t know, maybe something in finance that deals directly with startups?”
Does anyone really know?
At the time, I was living in NYC working for a software startup as an entry-level salesperson.
When I first applied for the job (see No Regrets for more on that) I had no idea what I was getting in to, I just knew I wanted to ‘learn how to start a company’ so figured the easiest way to do that was work for a startup.
While still small-ish, this wasn’t your typical startup. It was a few years old and had recently sold for $100mm.
Big screen TV’s mounted every few feet on the walls constantly refreshing the daily metrics of each individual sales rep on the floor. Push-up contests and faux flip-cup tournaments to start the day. The continual *explosion sound* and familiar headshot of my Vanderbilt classmate popping up on the screen to indicate a new sale. (She made about three times the sales as the next highest rep so we saw her face a lot).
I was making over 100 calls a day in a boiler-room sales environment hawking a piece of half-built software like a scene straight out of the Wolf of Wall Street.
After 6-months of this, coupled with the non-stop social life a recent grad experiences when they inevitably move to New York City – I was ready for a change.
I was home for a few days around Christmas when I ran into a family friend. I told him about what I was doing and how I was maybe looking to switch things up. He asked what I’d want to do and I responded with the canned answer from earlier.
I saw a twinkle in his eye…”Do you know what I do?” Nope.
“I just started a hedge-fund, we invest solely in startup IPO’s and we’re looking for a junior analyst to bring the team to five.”
Wait, so you’re a finance startup that deals directly with startups?
Now there was a twinkle in my eye.
“Exactly. Why don’t you come by the office tomorrow and we’ll talk.”
The next morning I hitched a ride into Boston with my dad, who just so happened to work across the street.
My daily attire was normally sweatpants or jeans, I hadn’t put on a suit since my cousin’s wedding and I wasn’t thrilled about it, but going into the big fancy building and doing the whole “Sign in, please.” > “Take the elevators on your right” > “Wait right here, he’ll be right with you. Can I get you a coffee or water?” thing was pretty cool.
About halfway into the ‘interview’, I asked him what they’d invested in and he showed me some of their portfolio.
“Emerald Oil, US Silica, you guys like the fracking space, huh?”
“How do you know those companies?” He asked casually.
“I have them in my portfolio. Same with those three.” Pointing to a few other companies on his list.
I was by no means a sophisticated investor – but since the day I started working in New York I’d invested whatever leftover money I had in the stock market.
Anyway, after showing him my portfolio (I don’t think he believed me at the time), I could tell he was impressed.
He left the room without speaking and came back with the job description for the position they were hiring.
“Take a look at this. Compensation and everything is already on there. I want you to talk to my partner, but we could have you working by Monday if you accept.”
Wait, what? I read a few Marketwatch articles and you’re offering me a six-figure salary, just like that?
My whole life was in NYC at that time. My job, my friends, my apartment.
“Umm, can I think about it?”
“Sure, but we need this position hired ASAP so meet with my partner tomorrow and let us know. It’s all very basic, background check, I think there’s a drug test, some standard paperwork, but we could have you up and running by next week.”
“Alright, sounds amazing, I just need to figure out what I’d do with my apartment and stuff. I’ll let you know tomorrow. Oh, and how strict is that drug test?” *Googles ‘how long does Pot stay in your system?’* “I may need a few weeks if it’s strict.”
“It’s not a big deal, don’t worry about it, we just need you here as soon as possible.”
I was pretty sure he dabbled in the pot game from time to time so my concern levels were very low.
Still, on my ride home, I did a little research, made a pit stop at CVS, bought some cranberry juice, some B12 pills, and began my ‘cleanse’.
Over the next two weeks, I met his partner, got the offer, borrowed a friends YMCA membership for the sauna, found a sublet for my apartment, quit my job, and moved back to Boston.
Oh, and bought 6 home drug tests for like $50 a pop. Passed every one.
It said online to wait a month, but these home tests are supposed to be legit, they need me to start ASAP, and they said it wasn’t a big deal if I failed so why wait? I thought to myself.
The day before I left for Boston I went to the nearest QUEST facility and took the test.
I spent the rest of that day with a friend of mine whose attempts to quell my anxiety were valiant but unsuccessful. I was a nervous wreck.
I moved home the following day and spent Sunday getting ready for what felt like my first day of school.
The next morning I drove with my pops, got my badge from the front desk, and headed up to my new office.
The office consisted of 3 older dudes (as a 24-year-old, 40+-year-olds are considered ‘older dudes’), and one young dude (around my age). Younger dude, or YD, began showing me the ropes.
By lunchtime, I was already liking it, but that afternoon I fell in love.
YD and I were on our way to an IPO roadshow presentation for none other than Care.com, a company I long considered a ‘competitor’ during my WAK Jobs days. I knew a ton about them already – the son of one of the executives was actually a Doer, believe it or not – so there couldn’t have been a better company for me to lose me ‘roadshow virginity’ to.
That night I gushed to my parents about how amazing my new job was. I hadn’t felt that good since, literally, ever.
The next morning I jumped out of bed, nerves gone, grabbed my coffee mug and headed into the city with my dad.
I spent that day learning, practicing, familiarizing myself with excel (Note to the youths: knowing how to do a sum= doesn’t mean you should put “Proficient in Excel” on your resume).
Before we left the office that day I got to chatting with one of the OD’s (old dude’s) and somewhere in that conversation my drug test came up.
“Oh, don’t worry about it. No news is good news, and if you fail, we’ll just send you to Natick with a whizinator and you can take it again.” He laughed.
Ha, love that. Alright, the last 2 ounces of anxiety I had evaporated.
I came into work the next morning as excited as ever. I can’t remember what we did that morning, but around 11am one of the OD’s got a call. Don’t quote me on the details here, but supposedly the parent company of the fund, the people who invested all of the initial capital, also ran HR. This call was from someone in HR informing the OD’s that my drug test had not come back yet and, technically, I wasn’t allowed to be in the office until it did.
Hmm. Okay, whatever, they didn’t seem phased by it so I didn’t get nervous, but those 2 ounces of anxiety crept back into my ‘nervous’ system. Pun intended.
My parents already knew about the test and everything so they didn’t give me a hard time that night.
The next morning, I was eating breakfast when I got a call from an unknown NYC number. I picked up and the operator on the other line started speaking, “Hi William, this is Sarah from Quest…we’re just calling to inform you that your test results came back positive…”
“Like, positive as in it went well or positive as in positive for drugs?”
I held my breath in hopes the next word out of her mouth weren’t “…positive for marijuana. You were over the legal limit. You’ll need to call your employer and let them know.” Click.
Gulp. Gasp. I couldn’t breathe. Anxiety rush. My skin, already remarkably pale, went ghost white.
Okay, calm down, just call OD and ask him when you can take the next test. Breathe.
I dialed OD, “OD, I just got a call from Quest. I failed. I fucking knew I took it too quickly. When can I retake it? I’ll definitely pass this time around.”
“Shit, okay, let me call you back.”
That was maybe the longest 15 minutes of my life.
Incoming call from a Boston number – I picked up – it was YD.
“Heyyyyyy, Woody, just heard, tough break man.”
“Yeah, this sucks, sorry dude. OD said I could take a retest so I’m about to call the Quest in Natick. Should be fine by Monday.”
“Yeahhhhh, so here’s the thing. We just got off the phone with HR and apparently, there is a ‘one-and-done’ policy that we were unaware of, so I’m really sorry.”
“Wait, what? What do you mean you were ‘unaware’ of this? What does that even mean?”
“Yeahhhhh, so we’re technically not able to hire you.” He sounded like the boss in Office Space. “I’m really sorry to be the one to have to tell you this. Best of luck, dude.”
“YD, please put OD on the phone,” I said in an increasingly aggressive tone.
“Ohh, yeah, sorry man, he just stepped into a meeting.” I wanted to strangle him through the phone, even though it wasn’t his fault.
“YD, I’m going to say this one more time – get OD on the fucking phone.”
“He’s in a meeting, man, there is nothing I can do.” He objected as if I was some pesky sales rep trying to pitch him a new office coffee machine.
Click. I hung up on him. And just like that, I’d Buckner’ed the job of a lifetime.
Anger. Embarrassment. Confusion. Sadness. Defeat. Anxiety. Mostly shock. Am I going to faint? Puke? Punch a wall? I don’t think I’ve ever had so many emotions swirl around all at once.
This is your fault. I said to myself. But, was it? I told them up front. They didn’t even care! We were joking about fucking WHIZINATORS for Christ sake. But now they didn’t care that I quit my job, moved out of my apartment to live with my freaking parents, left all my friends, and now was jobless. I couldn’t even get them on the damn phone.
I walked into my mom’s room and the tone of my skin clearly alerted her something was wrong as she almost fainted herself. “Omg – what happened?!”
“I failed the test. Apparently, they have a ‘one-and-done’ policy they were unaware of so I can’t work there.”
“Wh-what are you going to do?” She asked, desperately. As my mother, she too would have to carry the weight of this embarrassment.
“I need to have a new job by the time dad gets home or he’s going to kill me.”
It had to be the shock, or maybe the fear of death, that kept the anxiety at bay. I spent the next 6 hours pouring through my emails, connections, and job boards trying to rekindle some older opportunities with the companies I’d spoken to before accepting the NYC job, and by that evening I had miraculously set up a few interviews.
When my dad finally came home and I mustered up the courage to tell him, his reaction was actually much different than I expected – he had my back.
Now, that doesn’t mean he wasn’t angry and embarrassed and didn’t think I was a total shithead, but the verbal lashing I expected never came.
Note: I learned a valuable parenting lesson that day that I’ll always keep with me. No one was going to beat me up worse than I was already beating myself up, so all they could really do was be supportive, though I’m sure they wanted to strangle me.
I couldn’t sleep that night. I can’t remember if I cried or not but I definitely wanted to. I was so mad and the guilt I felt kept kicked me in the shins.
This is your fault, not theirs. You failed the test, you dumbass. You blew this, not them.
On a completely unrelated note, my cousin Tommy had recently gotten engaged and my mom was heading to Dallas that weekend for the engagement party. I asked if I could tag along and next thing you know, we were heading to Dallas.
It took about 8 minutes post-arrival for my cousin to sling his first ‘pothead’ joke. My mom gave me a wry smile that signaled “What, did you think I wasn’t going to tell them?”
I cracked my first smile since the ‘incident’, or ‘the asterisk’ as I’ve now started calling it.
It felt good getting away from my reality.
I was chatting with Tommy later that day and he mentioned a friend of his who was out in San Francisco working on a really cool company called CrowdTilt. I was 23, he was a few years older and had just raised $25mm for his company.
Damn. How do I meet this guy?
“He actually owes me a favor because he can’t make my bachelor party – let me text him and connect you guys.”
Completely serendipitously, my girlfriend at the time was heading to SF the following week for a conference, so the timing was perfect.
Tommy put me in touch with James who said he’d be happy to meet so I booked a one-way plane ticket to SF, fully expecting to never come back East.
My brief experience with finance gave me a bad taste in my mouth, I rationalized it as a ‘sign’ that maybe it wasn’t the life for me.
I decided the best way for me to test this was to revisit my ‘learn from someone else’ approach, but at a smaller company.
I set up a few meetings in SF with a few different companies- mostly big guys like Dropbox and Mozilla, but also a few smaller businesses.
The feedback I received was surprisingly consistent – “you shouldn’t work here, you should start your own company.”
But I don’t know HOW! Why don’t they get that?
It wasn’t until I met with James that he really put things in perspective for me.
There are a few ‘inflection points’ I think about when reflecting on my career.
The first came from the CEO of the NYC startup when he told me over a game of beer pong that I “didn’t have to climb the corporate ladder, I could build my own.”
That’s always stuck with me.
The second was ‘the asterisk’.
And the third was from James later that day.
We were grabbing a coffee and talking about his company, my experience in NYC, WAK Jobs, the reason I was looking for a job, all of it.
The more we talked, however, the more interested in WAK Jobs he became…
“So, what would you do differently than TaskRabbit?”
“Well I think TaskRabbit has a head start, but I hate their business model – I think the ‘reverse Ebay’ idea where the lowest bidder gets the job is a race to the bottom. I think they scaled out too many verticals, both professional and unprofessional, and everything is a bidding process – I think if you changed the model, made it more ‘on-demand’, and put a huge emphasis on quality you could beat them. But they already raised $12.5mm so looks like the jig is up.”
“What do you mean?”
“I mean, they’re way out ahead and well funded – how do you compete with that?”
“Woody, TONS of companies are way out ahead, well capitalized, and seemingly invincible until someone else does it better. That happens all the time. It’s a multi-billion dollar market – there won’t be only one player. If you think you can do it better – you need to do it.”
Gee, thanks. I thought. So does this mean I’m hired?
“Well I don’t know how to start a company, that’s why I’m here. I want to learn from you.”
“What do you mean you don’t know how? You literally just told me for the last hour about the company you’ve been running for the past 8 years!”
“Yeah, but that wasn’t a REAL company.” He looked at me like I had just sprouted a second head.
“I mean, like, we didn’t pay taxes or anything…”
He pulled out his phone, Googled LegalZoom.com, and began filling out an LLC application just to make a point.
“Okay, Okay, I get it. But I still want to work for you.”
“I’m not going to hire you and here’s why… the first person through the wall gets bloody, battered, and broken, but they learn 10x what the second person through the wall does. If you come and work for me, you’ll learn about your role, but you won’t be in the important meetings, you weren’t there when we first got off the ground, raised our first, or our second round of funding, so what you’ll ‘learn’, while valuable, won’t be what you need to create your own thing. Here’s what I want you to do – stay here for an hour or two, write down all your ideas if you HAD to re-start WAK Jobs, what and how you’d do it, then come back to my office and let’s talk about it.”
Well, I didn’t come here for a homework assignment but here goes nothing…
I spent the next two hours writing, drawing, writing more, and when I felt like I’d entertained his exercise long enough I walked back to his office.
“Shit, I’d invest in this if I had any money. You have to do this man, I’m telling you.”
And just like that, after a week of feeling like ants were crawling under my skin (anyone with anxiety will understand that feeling) I felt that familiar entrepreneurial spark…
I called my mom and the conversation went something like this:
“Mother! SF is great. Having a good time. Yes, James was super helpful. Yup, I could see myself living out here. Uh huh. Yup. Okay. Yeah, but I want to tell you something – I think I figured out what I’m going to do…WAK Jobs!”
Silence on the other end.
“So, like, odd jobs? For a career? Umm…”
“No, no, have you heard of Uber, the company where you push a button and get a cab? It’ll be like that – push a button on your phone, get a college kid. It could be big. Just trust me. Looks like you and dad have a new roommate!”
And just like that I was on another one-way flight back to Boston.
The next day, with my mind racing, I started thinking of names. Yes, I loved the name WAK Jobs, but I was afraid if people started searching for it the only results they’d see were Mafia hit men, articles about crazy people, or worst yet, something x-rated.
I needed something a little more ‘family friendly’.
I tried thinking of how someone would respond if you asked them, “Hey, can you help me move this couch?”
Or as your closest friends would say…”Hell no!”
What’s something else you would hear? Gladly? Ooo…I like that.
Gladly.com is available for $78,000 – would you like to purchase?
Surely! (ha) If I sold a few of my kidneys.
Gladly. Be glad to. Happily? Glad to. I’d gladly do it. Hmm. GladlyDo?
*GladlyDo.com is available for $2.99 – would you like to purchase?* Click.
That’ll do pig, that’ll do.
So there I sat, a few weeks after the biggest gut punch of my life, gearing up to strike off on my own to try to turn a pet-project summer job into a global behemoth.
People assume I had some master plan but guess what, I didn’t.
There was no light bulb ‘ah-ha’ moment, that moment occurred a decade before. This wasn’t the ‘big idea’ I’d been waiting for. Frankly, in the beginning, I didn’t even want to start it.
I fumbled, badly, and my next moves were gut reactions because my back was against a wall and I truthfully didn’t know what else to do.
Everyone deals with adversity differently. I know I do because, dead serious, somewhere in the time between the “Best of luck” call and the “GladlyDo.com domain purchased for $2.99” I literally started picturing myself as a Ninja warrior, back against a wall, with a hundred enemy soldiers closing in and the only two options facing me were 1. Surrender. or 2. Start swinging my ninja swords until I couldn’t swing anymore. And swing I did.
Ninjas? Maybe I do need to stop smoking…
As I said before, I’m going to try and steer clear of advice, but if you take anything from this story it’s that you can’t ever give up. Not ever.
When your back is against a wall, it simplifies your situation because there is only one direction to go – I encourage you to find you own ‘Ninja swords’ and head in that direction.
When something bad inevitably happens, whether it is big or small, it’s really not about what happened it’s about what happens next. You can’t control the past, you can only control how you respond moving forward.
While that is not exactly profound, it’s something I truly believe in.
Who knows, maybe this is what I was supposed to do all along.
I’ll never know for sure, but I’ve committed to looking forward and leaving regret in the past.
What I do know for sure is that I have the greatest parents in the world, and coming in hot off a botched job opportunity and a failed drug test at 24 years young, it couldn’t have been easy for them when I boldly said, “Just trust me”, but trust me they did.
Three years later, when I got to sit my family down and present my folks with a check with a few 0’s in it (they were one of my 10 investors), I can honestly say it was the proudest moment of my life.
Maybe God truly does have a plan, as my Dallas cousins were keen to remind me.
What I didn’t know at the time was that the next three years would be the hardest years of my life.
To be continued…
Subscribe for next weeks Episode 4 of WAK Job