Recruiting or Root Canal: What’s less painful?

Paul Ruderman
Mar 31, 2014 · 13 min read

Ok, I can finally write this post. In fact, it’s even easy to write this post now. Why? Because I finally filled the 5th of the 5 seats I earmarked for UpdateZen, the startup I launched late last year. And while we’re still a couple weeks away from our private beta, let alone a couple months away from our public launch, I am going to take a moment right now, pause, and acknowledge that we just hit a major milestone: I have my team!

“We’re through the looking glass, people!” — JFK, the movie.

Recruiting an early team of allstars to your startup is at once the hardest and most important thing you need to do as a founder. I knew this going in. But that didn’t make it any easier. Quite frankly, the task often seems near impossible, and is not entirely painless. Part of it is simple math:

  1. There is a limited number of truly exceptional people out there.
  2. Of those people, only a small percentage will have the skills, experience, drive and character that you are looking for.
  3. And of those people, only a fraction will fit personality-wise, with you and your early team.

To find your allstars, so much has to go right. Every ounce of persistence you can muster up is essential to giving you even a chance at finding your dream team. And yet, if you’re totally committed and focused, it will happen. To find the four brilliant people who have joined me and are now the core of UpdateZen, I went through quite a journey… at times exhilarating and inspiring, and at other times frustrating and energy-sucking… and full of more ups and downs than you can possibly imagine.

That said, I seem to have cracked the code and lived to tell. So in the interest of helping others recruit exceptional early teams, I’m going to try to document here how I did it. It is part art and part science, but it is also replicable. And if you want to build an early team of allstars, you have no choice.

If you've decided to start, then start!

After deciding to start UpdateZen last Fall, I set off on my quest to find my team. I knew what roles I needed to fill. And I needed A+ players at each one. I needed two full-stack developers (one iOS-focused and one web-focused), one designer, and eventually one marketer. I knew I’d made my job tougher by starting my company in Montclair, NJ — not exactly a bastion of tech talent, and by deciding to bootstrap and not raise any outside capital up front.

All told, I interviewed 36 developers, 22 designers, and 24 marketers over many months. And while that may sound like a lot of interviewing, that was by far the easiest part. The hardest part was finding these candidates in the first place. It is an incredibly competitive market out there for top talent. I knew that UpdateZen was/is an incredible opportunity, which made it easy for me to present well. And I knew what kind of people I was looking for; more than that, I knew that I’d know instantly once I’d found them. I am awfully picky about who I hire, particularly at this critical, early stage.

Net net… recruiting is NOT rocket science, but it is a process. This carefully cultivated guide below assumes you are a founder of a startup, you are bootstrapping as best you can, you don’t have unlimited resources to pay 25% recruiting fees, you will not settle for B players, and you know what you’re looking for. If so, read on.

How to hire an allstar team…

  1. Have a clear vision for what your company will look like once you’ve filled out all the early positions you’ve identified as absolutely essential.
  2. Know EXACTLY what you’re looking for. Have an unmistakable sense for what each of these positions require. Not a general idea… but a crystal clear sense.
  3. Clear your desk. Once you’ve decided you’re ready to hire for a given position, clear your desk of everything else you think you have to take on… so that you are free to commit 90% of your waking hours to searching, networking and recruiting for that position. You cannot recruit key early positions in your “free time.” First of all, you have no free time. Secondly, it will take every ounce of your being to persist through this process from now ‘til a given allstar is hired.
  4. Accept that the search will be all-consuming because it will be. So allow yourself to be fully consumed. Accept it. Embrace it. You’re going to find your allstar. You’re going to make it happen. It will suck along the way. It often feels impossible. Just. Simply. Impossible. At times it will feel like you will NEVER find the right person. And the thought of settling for B players, or even an A-minus player is so disheartening and deflating that you eliminate that option the moment it enters your mind.
  5. Well-written Job Description. Write an EXCEPTIONALLY articulate, unique, and distinguishing Job Description. Here’s a sample of my most recent one. I cannot overstate the importance of a well-written job description. Be as specific as you can about the kind of person and talent you are looking for. The more specific you are, the more likely that you (a) will attract top candidates who feel they are a fit for your unique startup, and (b) will disincentivize ill-fitting candidates from applying and thereby wasting their and your time. Remember, even if a candidate is great, experienced, and god’s gift to the world, if your opportunity doesn't suit their style, location, desired culture, or desired role, then he or she is not a “great”candidate for YOUR startup. So a job description with decent specificity will help to disincentivize these “great” candidates from applying as well. The more details you include about what the position will be responsible for, the more likely you’ll be to rule out vagrants who submit their resume to every job posting they see with a matching word (ie. “marketing”) in their job search. If I’m hiring a marketing cat for my tech startup, do you think I want 25 people who’ve done marketing for Verizon Wireless to submit resumes to me?? Hell no! Now, I’m not saying you won’t get tons of resumes that aren’t up to snuff. I’m just saying you want to do everything possible to “write out” ill-matched candidates in your job description. This will effectively reduce the number of crappy resumes coming in, and save you boatloads of time.
  6. Cover Emails. Require that submitting candidates write a personalized cover email to you explaining why your startup interests them and why they are the best candidate for the job. If they don’t take the time to write this personalized cover email, don’t even look at their resume. They’re not serious. And they probably can’t write. And if they do write a cover email, you’ll instantly see if they can write. (For me, if you can’t write a well-written, concise cover email, then you’re probably not the right cat for my company.)
  7. LinkedIn Profiles. Review candidates’ LinkedIn profiles before looking at their resumes. Hell, instead of looking at their resumes. Resumes are dry, non-dynamic, dead documents. A good LinkedIn profile contains everything a resume does, and then some… and the “some” is more important than whatever’s on the resume. The “some” includes written references from past/current colleagues. The “some” includes a candidates’ number of LinkedIn connections. (So someone applies to your company who considers himself a tech startup marketing person, but has just 41 connections on LinkedIn? Out! ) Do they not have a photo? Out! (Not because I want to see what they look like, but because in this day and age, if you have a LinkedIn profile without a photo or caricature of yourself, then you’re just not serious. Or worse, if you chose to use as your LinkedIn photo one of yourself with a backwards baseball hat pal’ing around with your college buddies in a bar, you’re not my cat.) Do you see grammatical errors in their LinkedIn self-descriptions? Out! As a plus, on LinkedIn, many top candidates will include links to their personal websites…. always a trove of “color” on a candidate. And on and on and on. I tell candidates to only send me LinkedIn profile URL’s and NO resumes.
  8. Networking on LinkedIn. Network your ass off on LinkedIn, search extensively on LinkedIn, send LinkedIn InMails to candidates that seem exceptional from their profiles alone, regardless whether you have a personal connection to them, and regardless whether these candidates claim they’re “looking” for new opportunities or not. Successful outreach INMAILS include short notes that tease the opportunity, tell a little about yourself, and link to that well-written job description! A well-written short INMAIL gets them interested… and then the kickass job description — and your gorgeous website — grabs them by their lapels. Here’s a response from an A+ candidate whom I cold-emailed based on nothing more than his exceptional LinkedIn profile: “Paul, let me start by saying that I will typically politely decline these requests because I am with a well-funded, and fast growing startup already and not really looking to move on. However, your job description for UpdateZen was so well-written, and the product (and pain it solves) that you describe is so exciting that I cannot help but want to speak to you. Seriously, that is a brilliant document. And if that’s how you manage/lead this business, I’m interested.”
  9. Use Recruiters Intelligently. Recruiters can be your best friend. Or they can suck up your time and take all the money you don’t have. Find a good one — as I have — and they are one of your best assets. But you can’t afford 25% fees. No bootstrapping startup can afford 25% fees. So what do I do? Having hired dozens of great people over the years, I’ve built up a stable of top recruiters who are willing to work with me for a much-reduced fee. Why would they? Because they want to be part of your startup as you grow. I have a handful of superb recruiters that I send JD’s to. I tell them to do minimal screening (saving them time), and just send me LinkedIn profiles. I quickly review the profiles. If interested, I connect with the candidates. You can’t work with just ONE recruiter. Find 3-5 great ones who will work for a reduced fee. They’ll make more money with you in the long run because you’ll send them way more job postings, and eventually you will be able to pay their 25% fees. But not just yet.
  10. Ask friends to broadcast your job opening. Ask friends in your industry to post a link to your Job Description on their LinkedIn status, Twitter feeds, and across their own networks. Again, you never know who is going to read some post, some tweet, some blog, some email, some job posting, and think of their friend or colleague who is just perfect for the gig.
  11. Flood the Market. This is the key. Flood the market with outreach. I post job descriptions everywhere that is even remotely relevant… wherever a great candidate might go. Angel List. LinkedIn. Monster. Dice. Hired.com. Employment Crossing. Craigslist. StartupHire.com. Dribbble. Behance. You NEVER know where your eventual candidate might be… so plant your seeds in many places. Remember, all you need is that ONE great candidate. Just one. In fact, to drive home the point, let me quote the one great pioneer of the market-flooding philosophy, Mike Damone, because his insight is so perfectly relevant. (Apologies to those of you who aren't fans of Fast Times at Ridgemont High).

Mike Damone: “I mean I just send out this vibe and I have personally found that women do respond. I mean, something happens.”

Mark Ratner: “Well, naturally something happens. I mean, you put the vibe out to 30 million chicks, something is gonna happen.”

Mike Damone: “That’s the idea, Rat. That’s the attitude.”

Notwithstanding the completely inappropriate lines that follow this exchange — which I’ve purposely refrained from including, and which I don’t condone — Damone has it about right. He’d be a great recruiter for his own startup. You put the feelers out there. You flood the market with outreach. You post in the most likely and unlikely places where you just might find that special person. I found one of my brilliant developers through StartupHire.com, a tiny site that really gets very little traffic relative to the big boys. I got a handful of clickthrus and applications on StartupHire.com in the first couple weeks. Nobody interesting. And then, guess what? One of the next applications was from Stefan, my exceptional web developer who happened to be looking for a startup just like UpdateZen. He was a perfect fit for us. So a nominal posting fee on StartupHire.com turned out to do the trick. Had I not taken a wild chance and posted on this site I’d never heard of, I wouldn’t be working with Stefan today.

Ok, so I found some great candidates, now what?

Work quickly. Review each resume or LinkedIn profile as instantly and expeditiously as you can. The great people get snatched up quickly. They have their choice of jobs and companies.

Refine your pitch. You need to SELL these allstars. Just like you’re going to sell your early customers. And just like selling early customers, recruiting doesn’t scale! You need to individually sell each great candidate that you’re fortunate enough to hop on a call with. If you believe in your product, your vision, your team, and yourself, then this part should be a breeze. I LOVE selling the UpdateZen opportunity because I know it’s going to be a huge success, a ton of fun making it a huge success, and quite honestly there’s nothing I’d rather do.

Conduct your initial interview via Skype video or Google Hangouts video. No audio calls. Schedule a 30 minute video call with each seemingly great candidate. Conducting the initial interview via a video call will give you a much quicker and more accurate sense of the candidate, and them of you. You’ll know if your energies match or clash. You’ll know — usually within 5 minutes — whether the candidate is a possibility. And on the flipside, you’ll know almost instantly if your candidate is an absolute NO. If a no, you can try to end the call early, but that’s not always the right thing to do. You asked them for the call. Give them the time. Plus, even if you don’t end up working together, you’re each making a new contact. Never a bad thing.

Conduct second interviews in person. Now, if the video call goes well, either extend it beyond 30 minutes, or set up a second video call right there and then. Or better yet, if you feel it just may be a great fit, invite the candidate to your office for a visit promptly. Then we get back to normal recruiting processes. They come in, they meet your team, and if it’s a fit after the meeting, tell them you’re making them an offer, make the offer quickly, and make a serious offer. Don’t lowball them. If you really want them, make them the most generous offer you can afford to make. If it fits their needs and they want to join you, great. If it doesn’t, then you both move on quickly.

Reference calls. Conduct a minimum of 2 reference calls. DO THIS! Not as a formality, but because if you’re good at making reference calls, you can obtain phenomenal “color” on the candidate — how they optimally work, what makes them tick, what challenges do they need to overcome, what are they better at than anyone else, how much did their colleagues like them, and most importantly… what kind of character and integrity does the candidate have? You can’t get this from a resume or a LinkedIn profile. In fact, you can’t always get this from an in-person interview, either. You can, however, get this from a great reference call. I find them invaluable.

It ain’t over ‘til the fat lady sings. You may get pretty deep into the process of finding, interviewing, recruiting, selling, offering, hiring and starting a new person… and then BAM, it just doesn’t work out. Expect this. It happens sometimes. Anywhere along the line, the thing can fail. Everything seemed perfect, but then he wasn’t a great fit with your team. Or she turned out to not be what she represented herself to be. Or any other number of possibilities. Pull the plug quickly! And if you do, it will crush you. So how do you deal with it? You just deal with it. You’ll be mighty depressed that night. That’s fine. Take the night. Be depressed. Be pissed. Get frustrated. Stop recruiting for the night. Go home and watch a ridiculously mindless movie, go drinking, shoot hoops with your kids for 3 hours, whatever floats your boat. But commit to the next morning’s plan: You wake up, you drink strong coffee, and you start again. You flood the market. You network like a madman. You interview aggressively. And you keep it up until you have your cat!


And that’s it! No, hiring an early team of A players is not easy, and it ain’t for the faint of heart. But yes, it is possible and there’s even a method to the madness. I hope I’ve clearly articulated this method for you in this essay. Filling out your team with A players won’t happen overnight, but it will happen. And the most important thing… persist! Persist persist persist! Don’t give up.

Good luck!


P.S. The aforementioned notwithstanding, if I needed to hire another allstar right now, and you said, “Hey Paul, I’m gonna give you a choice. You can go through the process you’ve outlined above and probably have your ideal candidate in 3-4 weeks OR you can go through a 2-hour root canal right now without novocaine but I’ll guarantee you’ll have your ideal candidate at the end of the 2 hours… what would you choose?” I’d choose the novocaine-less root canal any day of the week. Recruiting is THAT hard! But since no dentist has ever offered me this magic deal with the devil, I’ll stick to recruiting!


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    Paul Ruderman

    Written by

    tech entrepreneur; creator of things from scratch… companies, songs, podcasts, blogs and bands; candidate for best dad ever, well maybe…

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