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Do you enjoy reading reports from the Academies online for free!

Can we really crown Uber king already? (Original Post)

It seems like once a week an on-demand startup is either coming or going. The on-demand craze is in full effect and shows no signs of slowing down. While W2 vs. 1099 battles rage and people continue to question the validity of the business model – it seems clear that when it’s all said and done, there will be a handful of losers and only a few ‘winners’. 

Just last week Shuddle announced it was closing its doors, yet the rise in failing companies hasn’t stopped hopefuls from entering the market. The question is, what’s different about these new companies? Are they better positioned to succeed? Or doomed to fail like many others? 

Startups like Magic offer to “bring you anything,” which can be a helping hand for someone who can’t get around too well or is ill. They recently launched Magic+, on the other hand, which buys into the needs and wants of the super-wealthy. You can think of them like a concierge service providing the niche-specific needs of the ultra-rich (think ‘meet a celebrity’, ordering you an on-demand helicopter or moving your boat across the entire country).

Catering to this audience in the on-demand startup world might make sense financially, but are there enough?

Useful, But Still Pricey

Magic+ isn’t alone in this world of high-end startup culture. Another new startup, Recharge, allows the user to rent hotel rooms by the minute in order to rest while on the go. This sounds like a great idea for the majority of folk who travel a lot for work and leisure and is something almost anyone could jump on.

Until you see the toll that nap has taken.

Most popular in San Francisco, which is the hub of the “sharing economy”, a quick recharge in a hotel with Recharge will run you about $.66 a minute, or $40 an hour.

Would you pay $40 for an hour nap?

Enjoy It While It Lasts

Can we really crown Uber king already? 

With increased financial pressure from student loans, rocketing rent prices, and practically 0% savings rates, it’s hardly a surprise that millennials aren’t buying homes – we don’t have any money!

No wonder services like Uber and Lyft have been so successful marketing to young people – why own a car when you can have one at your fingertips without the hassle of parking, upkeep, and gas?

Once Uber became everyone’s private driver, they set off a domino effect that Uberized virtually every industry. We’re spoiled with the ability to cheaply order anything from food to groceries to laundry services at the push of a button.

We, the customers, have reaped the rewards of these services for some time now and it’s been a hell of a free (discounted) ride.

But when is the other shoe going to drop? Most of the companies copying the Uber model are paying $1 to make .80c – how long can that last? 

Fueled by incomprehensible amounts of funding at valuations even SaaS companies are jealous of, they redistribute lots of that funding to customers by way of heavy discounts, oftentimes pushing their profit margins into the negatives.

Basic math here – if you have a negative margin, the more you make, the more you lose.

Even simpler, if you have to pay $10 to get a new customer and you only ever earn $8 from that customer, you’re losing $2 for every new customer you get.

The Hangover GIF

I’m more of a Michael Scott “talk to me like a 1st grader” type of guy, but Google ‘unit economics’ and ‘economies of scale’ to get a more sophisticated explanation of that concept if you’re still confused.

Bottom line, unless there is a way to make up that loss in the future, you’re going to lose money forever. Users don’t necessarily equate to dollars.

In essence, these companies are donating more and more money to the general public by way of subsidies. And, while I personally appreciate that, if I were an investor, I’d be wary. A lot of these companies will never be able to turn a profit, especially in a competitive market.

Like two gas stations across the street from one another, if Lyft lowers their price, they force Uber’s hand, eventually eliminating all profits in an effort to squash each other. It’s Econ 101 – just ask Netflix and Blockbuster back in the 2000s. Or look at all the food delivery companies.

Now, if they decide to raise prices or keep pricing competitive and mutually beneficial, it opens the door for some OTHER ‘soon-to-be-Unicorn’ to raise a bunch of money, undercut their prices, steal market share and force them to respond (see Juno, Via, Fasten, etc.), which means both Uber/Lyft now have to go lower to squash the newcomers. Are you dizzy yet?

Despite all of this, we haven’t even touched the subject of the actual people driving these services (pun intended). Uber will struggle financially, but they’ll sell a ‘growth and disruption’ story to continue to raise piles of money at nose bleed valuations. And if the drivers continue to be unhappy with their slice of the pie, they’ll try to unionize, sue, strike, or eventually quit when they realize they aren’t making $35/hr like the ads say – after expenses, it’s probably less than half that. 

So, for Uber to turn a profit, only a few options remain. Slow spending and raise prices (which in a competitive/commodity market, as we mentioned before, is tough to do) – OR – automate the people away. While autonomous cars give Uber the 80% margin back, they create a slew of other issues.

Who knows, maybe Uber ends up being the operating system for an autonomous GM car fleet or something, but it’ll be a long time before we see the driverless dream come to fruition. 

So, to you other Uber-for-X’s out there – unless you have really deep pockets to achieve massive scale, or simply survive long enough for someone to buy you, providing a cheap luxury good at already thin margins is going to be tough.

In the last few weeks, we’ve seen price increases and driver pay cuts from some of the darling Unicorn companies such as Instacart and DoorDash. Why? I’d bet they’re feeling pressure to start turning a profit.

NOTE: Unless your name is Amazon, it’s going to be hard to operate at a loss forever. SECOND NOTE: In general, try not to compare yourself to Amazon.  

There is still no app to tell the future, but if these recent price hikes are any indication of what’s to come, I’d say it’s time to start saving your pennies.

Could be a year or could be 5, but when investors inevitably start fearing the end of the bull market that’s been chugging along for 6ish years they’ll start paying more attention to profits again. And when Uber and the rest of the merry band of Unicorns are forced to hit the IPO market and give everyone a glance under the proverbial kimono – I’d caution jumping in – you’re likely the greater fool at that point. 

But you tell me – is it too early to crown Uber king?

But, how do I get started? … JFGI

Remember when teachers used to say, “There is no such thing as a dumb question”?

They were lying.

I hate to be the one to break it to you, but there are PLENTY of dumb questions.

Allow me to clarify… I don’t think the people asking the questions are dumb, and I’m surely not insinuating that I’m particularly smart—hell, I had 12 people point out typos in my last blog and I had to spell check the word “insinuate” just now (it does not have a C in it).

My definition of a “dumb” question is one that you didn’t put any thought into answering yourself before asking.

So when my older brother, whom I love dearly, called me a few years back to ask how to start an LLC, I did what any younger brother would do… I messed with him a little bit.

Quick backstory – my brother Sam is a very talented actor/comedian/writer/producer. If you need someone to roast your parent at a 60th birthday party, he’s your guy. But when it comes to business, his brain definitely leans left.

We’d worked together to film my first ever commercial (which I recently re-uploaded if you care to see his handiwork and my acting debut 💁‍♀️). After racking up over 100,000 views between Facebook and YouTube, I thought it was something he should run with—but he was hesitant.

That video led to another gig with a real estate company in Boston that also did very well.

When he finally came to his senses and decided to pursue this direction slightly more aggressively, I was pleasantly surprised to receive his phone call.

“Yo…(small talk)…yeah, so I’m going to do the video thing. I’m calling it Cowbell Media. Arden’s building me a site. How do I start an LLC?”

Now I absolutely LOVE that my older brother would turn to me for advice, but I couldn’t remember for the life of me what actually went into getting GladlyDo set up.

I remember using LegalZoom—you fill out some forms, pay a fee, and bada bing, you’re in business.

But I couldn’t let this opportunity slip. So I hustled over to my computer, googled “how to start an LLC,” and clicked on the very first link.

I asked Sam to get a pen and paper, and for the next 15 minutes, proceeded to read the steps off one by one as if they were entirely original thoughts.

After we hung up, I went to a website I had recently discovered called LetMeGoogleThatForYou.com (you’ll be shocked by what it does) and sent him one final jab.

If you don’t have time to watch that 5-second video recording of me googling “How to start an LLC,”… it’s a 5-second video recording of me googling “How to start an LLC.”

Yes, I was being a particular breed of asshole that day, and it would have been far easier to use a phrase I’d started saying a few years prior, but where’s the fun in that?

What I should have said was “JFGI,” an acronym I’ve grown quite fond of in recent years.

It stands for “Just F*ing Google It” (sorry for the harsh letter, I throw it in there for a little razzle-dazzle).

Since I started writing this post I’ve googled a spell-check, which side of the brain is creative, a YouTube video, and if it’s okay to cook chicken that isn’t fully thawed (it is, you just need to cook it longer).

While Google is incredibly useful in my personal life, I’ve found it to be even more useful in my business life.

When I was first starting GladlyDo I had absolutely no idea what I was doing. Like, no idea. I literally googled “how to start a company.”

Then “how to start a tech company if you don’t know how to code.”

The wealth of information that is only a few clicks away never ceases to amaze me.

I’ve recently spoken with a few “thinking about starting a company but don’t know how to start”-type folks, and thought it might help to demystify the perceived difficulty it takes to actually start a company. (Important note: start, not necessarily succeed.)

Here’s what I did…

“how to start a company”

Name, check. Formation, Legalzoom. Bank account, TBD.

“how to build a website”

hmm, websites cost money

“how to get money for your company”

fundraising, loans, sell a kidney, this might be tough…

“how to build a website for free”

ehh, Wix isn’t going to cut it

“how to find a website developer”

this Upwork.com thing is awesome, definitely copying some of these features

“what is a ‘scope of work’ for a website”

okay, just write everything you need it to do

“how much should a website cost”

ugh, way too wide a range

*Posts the “Scope of Work” to Facebook*

Nice! My college friend McArthur can do this for me. It’s going to cost $15,000…

“how to get money to pay for website”

lot of options, maybe I’ll raise money

“how to get investors in your company”

woof, that’s going to take too long

“what do you need to secure a business loan?”

that’s a pretty high interest rate, wonder if I can get a backer

“how to ask your parents to back your loan”

Personal loan secured. (mistake #1 – more to come on this in future blog)

“how do you design a website”

okay, no idea how to use photoshop, pen and paper it is

“what swag should I buy for my startup”

300 t-shirts sounds good (🤦‍♂️ mistake #2)

“how to set up a Facebook business account”

This will go viral for sure (it didn’t, mistake #3)

“fastest and easiest way to get customers”

ohh, this is a great how-to from Harry’s launch. I need referrals.

“how to get referrals”

this referral article will help

“when is the best time to send a company launch email”

alright, here we go…

A few simple Google searches and voila, I had a “real” business.

There is obviously a lot more to it—and again, this isn’t a recipe for success—but it was just enough inertia to get me moving.

It’s easy to start, and sometimes that’s the hardest part.

So for any of you hanging around the rim, it doesn’t need to be sexy. Sometimes you need to just get in the gym and start moving.

The information you need is out there, Just Fucking Google It.

Reach out anytime! wklemmer@gmail.com

Well, I Buckner’d that one.

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?”

“Sure. Surely.”

“Happily!”

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…

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This may come as a shock…

(3-ish minute read)

This may come as a shock, especially to those who know me well, so sit down and buckle up.

I’m a “talker”.

I know, I know, a truly brave admission.

Gift of gab, extreme extrovert, social butterfly, *cough* loud, obnoxious, center of attention *cough* – there is no shortage of adjectives that have been used to describe me. In my defense, I could talk before I could walk (seriously, ask my Mom) so it’s not like this is a new development.

Recently, however, I’ve tried to be more conscious of that.

I try and ask more questions than I’m asked. I try and listen more than I speak (gulp). I try to be present and interested during conversations I’m not particularly excited to be in. Try being the operative word.

“God gave you 2 ears and 1 mouth, so listen twice as much as you speak.” Yeah, yeah, yeah, thanks, Mom.

I know I’m not great at it, but I’m trying because I notice when other people aren’t great at it and, frankly, it drives me nuts.

Like, what is behind me that you keep looking over my shoulder? Why are you texting in the middle of our conversation? Stop saying “right, right, uh huh, okay” after everything I say.

Wait, I’m not like that…am I? 

Anyway, the last few months I’ve had a lot more free time on my hands and I’ve been spending quite a bit of time networking.

A very common question I’m asked when meeting new people is, “So what’s your story?”

Simple enough, right?

Wrong. I mean, how much time do you have? Where should I start? Middle school? High school? College? Post-college? Shit, I’m only 28, how do guys twice my age answer this question without needing a nap in between?

As a form of practice, when I ‘tell my story’ I typically try to give an aggressively Sparknoted version, which still requires an Ace Ventura Inhale.

“Started an odd job company in middle school, did it every summer through college, blew all my money first semester, wanted to bring WAK Jobs to colleges but was too busy (lazy) so, instead, had a few friends start seedling versions all over the country. Graduated and started working for a startup in NYC…***…jumped on a one-way plane ticket to SF, got convinced to do WAK Jobs full time, one-way ticket back to Boston, started GladlyDo the next day. Took out a loan, grew the business for a year, raised some money, grew the business for another year, started pivoting to the B2B space, went to raise my second round of funding, met a Venture group in Philly, negotiated for 6 months and eventually sold them the business. Moved to Philly, relaunched as Laborocity, grew it to a multi-million dollar business, went to raise money but ultimately was bought out by our investors, took some time off to travel a bit, visit family, and now looking for something new and exciting.”

*Ace Ventura Exhale*

As I use this blog to wind through the finer details of those ‘chapters’, I feel it’s important I fill in as much color as I can, even if it’s a shade darker.

Well, hidden in that “***” above is a little known but wildly important part of my story that I leave out 98% of the time I tell it.

It’s one of the few things I don’t talk about, at least not publicly, but I’m starting to think maybe something I should because…

*Pulls out soapbox*

…we live in an Instagram glorified culture these days where you only see the “best” picture, the trophy, the achievement, but I think that misses the bigger picture.

I miss the old days, where someone would put up a Facebook album after a night out and you’d anxiously scroll through to see if you had a new default pic, but more importantly, which pictures needed a swift de-tag. That damn double chin!

No photoshop, no filters, no “influencers” in a bikini posting how FitTea changed their life.

The closest thing we had to ‘airbrushing’ was using Paint to color over beer cans or blur out the background so your parents didn’t know whose house you were at. (Mom, if you’re reading this, do NOT check the Halloween picture in my high school yearbook!)

My point isn’t to bash social media (I’m scrolling Instagram drinking FitTea as we speak 💁‍♀️) and it’s certainly not a ‘hot take’ to claim that we glorify everything online – I just wish we could peek behind the curtain more.

To me, it’s about the lows. It’s about the hardship and the struggle and the tireless effort. I’d rather listen to someone talk about the ten times they screwed up over the hundred times they succeeded any day of the week.

I just find it more genuine, more relatable, and frankly, more helpful.

So, with that in mind, I will do my best to be brutally honest throughout my story whether there is a lesson to be learned or not.

It happened, so here it is.

With that in mind, I can say without one ounce of exaggeration that the one pivotal moment I eluded to earlier changed the course of my career, and likely my entire life.

It was the day everything seemingly ended for me. But, five years of hindsight later, I can now say it was the day my life truly began.

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Previously, on WAK Job…No Regrets

No Regrets? What was I thinking…

(2-minute read)

Scene: Senior year of college. First ‘real’ job application. Applying to be a salesperson at a cool software start-up in NYC.

I’d never applied for a job before so I enlisted the help of a college career advisor who had some sound advice.

“For sales roles, they want to know two things – you’re okay with rejection, and you want to make a lot of money.”

Wait, I thought talking about money was a faux pas…

“Don’t say something dumb like ‘I like people!’ if you like people so much, move to China. You’re here to do a job and that job is to make the company, and yourself, a lot of money.”

So leave out, “I’m a people person.” Got it.

I spent the next few hours pouring through Glassdoor reviews which just so happened to have a lot of the interview questions posted…

“How many ping pong balls can fit in a 747?”

“Sell me this pen.”

“What’s your biggest weakness?”

I wrote and rewrote my answers and practiced until I knew them cold.

I’ve never lacked in the anxiety department and when it was time for the interview, I felt like I’d just gone 90mph by a speed trap.

The first few questions were pretty standard and I was able to use my rehearsed responses to answer them, but then things got interesting…

“If you could be any animal – what would you be?”

WTF? Is this a job interview or sorority rush? I think I picked a dolphin.

“If you could teleport 50 years in the future or past, which would you pick?”

Okay, maybe this isn’t so bad. I settled in and answered these odd questions as if we were talking over a beer. They were actually kind of fun.

Everything was going great until the last question caught me by surprise…“If you had an autobiography, what would you call it?”

Uh oh, I hadn’t prepped for this one… “No Regrets” I blurted out.

FUCK. What a dumb answer. I immediately regretted that decision. I’m such a tool.  🤦‍♂️

But before I could finish my internal self-deprecation my mouth continued on autopilot… “but let me explain that…I don’t mean that in the fratty, millennial ‘bro’ way it sounds – what I mean is I’ve been very fortunate so far in life. I have two awesome brothers and parents who would do anything for me. I grew up in a nice town and have great friends, I have traveled, been on fun sports teams, and had every opportunity a kid could dream of. I’ve been able to take risks, make mistakes, fail, fall and get back up because of the support system I have and I never want to take that for granted. I know not everyone is handed those same opportunities, so it’s up to me to capitalize on them. When it’s all said and done and I’m 95 years old talking to my great, great grandkids, I want to have as few regrets in my life as possible. I want to use my opportunity and gifts to teach one day and I want to be able to look myself in the mirror and honestly say I helped everyone I could along the way. While it may sound cheesy, I think it’s important and it’s how I want to live.”

Where did that come from? What was the question again? Who am I?

Kidding aside, I don’t know where in the bowels of my brain that unfiltered, unrehearsed rant came from, but I’ve been trying to live up to it ever since.

I got the job, but it’s why I eventually left. It’s why I bought a one-way plane ticket to San Francisco and five days later bought a one-way ticket back to live in my parent’s house and start a business. It’s why I risked relationships and took money from friends and family. It’s why I drove Uber and shoveled driveways to keep the company afloat. It’s why I eventually sold the company and moved to Philadelphia not knowing a soul there to start all over again. It’s why I’m writing this.

It is so easy to fall into a rhythm of “I’m going to…” and “One day I will…” but I challenge you to do your best to break the cycle. Take the job – move to a new city – start the company – ask your crush out – say yes to drinks on a Monday night – stay in touch with people who matter to you – do something nice for someone for no reason – send a note to someone going through something negative or congratulate someone’s accomplishment – whether it is big or small, stop thinking about it and just fucking do it.

The older I get, the quicker life seems to move. Windows of opportunity come and go and it’s up to us to jump through them. My 2 cents – leave regret in the past.