Why You Want to be the *Second* 1st PM

Wait, what??? What is a “second” first?

If you’ve been a first product manager (PM) at a company before you know what this means. For the rest, let’s take a look.

What is a first PM?

The first product manager (PM) is exactly what it sounds like: it’s the first product manager hired at a company.

Typically, that means you’re taking over for one of the founders who is now too busy to handle the responsibilities.

In other cases, the company has not really had anyone serve as product manager, and finally hits a point where they recognize the team needs stronger product direction and focus than a variety of people can figure out ad hoc.

In both cases, that usually happens somewhere between employee #8 and 20. So the team is small enough to be nimble, but big enough to make some serious progress.

So what’s a *second* first PM?

Joining a company as first PM is a big risk. The company usually has some traction but not a lot. They’ve likely raised some money (or have substantial revenue), but not tens of millions in the bank.

However, that’s not the greatest risk.

The greatest risk is that the founders that hired you don’t know what they really need.

Unfortunately, the first first PM often ends up being a sacrificial lamb so that the company can figure out what they really need in product leadership.

Today, we take a look at why it happens, and what product people considering being a first PM should think about before taking such a role.

 

The Unique Challenges of the 1st PM

The first PM is a special job. You’re coming in to bring order to chaos, and disciplined habits to a company with some (or a lot of) traction.

With that comes a lot of challenges starting on Day 1:

1) Metrics: You may or may not have *any* metrics, which makes decision making looking back hard. If there are some analytics implemented, you’ll likely be the first person to seriously look at them regularly and use them to make product decisions.

2) Resources: The team may or may not be fully staffed. Chances are you’ll be working with a mix of junior hustlers who were early and are “figuring it out as they go” and the first executives brought in to bring order and scale. In particular, you may not have a full time designer to work with.

3) Process: Unfortunately, what worked in the “Figure it out” mode of early days, doesn’t work so well with a dozen engineers and a growing roadmap. You have to work hard to get buy in so that a little process can help everyone’s work go more smoothly. Sometimes, founders can be the most resistant to this.

4) Founder Passion: Giving up their baby to let you run product can be really hard. A founder’s vision & gut for what is “right” has gotten them incredibly far, and now you need to work with them to chart the right course forward. There’s a fine line between executing their vision, and being stuck forced to build things they want that you know aren’t the most important thing.

5) Founder experience: If they’ve never worked with a PM before, they may not know what that really means. Given how vague product responsibilities and outputs often are, it’s not uncommon to hear “I like how this project/new feature is going, but I have no idea how you’re contributing to that.” 

Now, these challenges make the job uniquely difficult, but also can generally can be overcome as long as you don’t face too many of the above issues together.

Unfortunately, it’s their combination with the 2 biggest factors below that leads to a first PM’s departure, and a second 1st PM being hired.

 

Why the *first* 1st PM often ultimately fails

Most 1st PMs are experienced product leaders. Whether they’ve been a product manager for years, or started their own companies, they’re generally very T-shaped employees that know how to deal with a variety of challenges.

Despite this, being the first 1st PM still does not work out in a lot of cases. I’ve seen this firsthand and commiserated with fellow PMs who have been through it.

So what are they unable to overcome? Why do they ultimately fail?

1) The founders don’t know what they really want and need

The earlier a startup is, the more haphazard the hiring process is. At 10-20 employees, they often don’t have a recruiter (or often any HR) on staff, so they’re making it up as go as they hire people. This means many hires are directly from their network or referrals from there, without a lot of vetting.

With all the problems that have built up leading them to realize it’s finally time to hire a product manager, they start asking around for product people they know.

Eventually, someone gets introduced to them that understands this early stage startup world. In the interview they’ll be able to point out some obvious problems the product or product team has with plausible solutions.

This makes the founder think, “Yes. I need this person to solve these problems!”

Unfortunately, when they hire this person, they later realize that while those problems did need fixed, they weren’t *the most important thing* they needed in a PM.

Instead, these founders slowly discover that the skills of the PM they hired don’t align as well as they hoped:

  • Market: Are they well-suited for the nature of your market? Do they relate well to your target customer?
  • Stage: Are they comfortable with where your business is in finding product/market fit? Pre-P/M fit requires a level of experimentation and exploration some PMs can be very uncomfortable with, and is very different work than post P/M fit.
  • Non-Technical: Is it a very technical product? Then your UX issues may seem glaring now, but won’t matter when you’re trying to make core feature innovations quickly.
  • Too-Technical: Is technology not the most important differentiator in your market? Then, a technical PM may relate well to a technical founder, but not bring the customer empathy or design skills that are more important in your market.
  • Rapport: The PM and the founder they report to have to build a very close relationship. If they think too differently, or clash in personality, it won’t work.
  • Culture: How the company operates often follows the habits of the founders. If they’re disorganized it can be very hard for a process-driven PM to bring in process and get buy in from colleagues if the founder isn’t supportive of those changes.

Hiring a first PM is like the story of Goldilocks; you have to try a few to find the one that’s “just right.”

Unfortunately, first PMs often end up being like Goldilock’s first bowl of porridge; not quite right.

Given product management comes in many different flavors, it’s easy for founders to choose the wrong one for any of the above reasons, or similar ones.

Note: this post does a great job of grouping and explaining different types of PMs.

2) The company isn’t fully established

The other side of the coin is that this is still an early stage company. Even if at the time you hired them, the PM is the exact right fit technically, market-wise, and culturally, it still may not work.

Why? Because if your company makes a major change, so does the PM you need:

  • B2B vs. B2C: If you take the leap from consumer to being a B2B product, there’s a good chance that your first PM won’t be the right fit on the other side.
  • Moving Up or Down Market: Someone great at building for the enterprise with many stakeholders and permissions leveling may not be good at building for SMBs who are used to free trials, and a self-serve approach.
  • Solution format: If you were a consulting and services heavy business it’s great if they’re from that world as well, right until you want to build a product that stands on its own without any of that.
  • Industry passion: Just because the PM was excited by your original mission and industry does not mean they’ll still be in love with your business if you suddenly have a whole new customer base to work with that’s very different.

On top of all this, as other roles are hired, what the PM needs to do could change, too. For example, if you hire an amazing designer who loves usability research, then a PM strong in that is less important than another unfilled gap.

One person’s trash is another person’s treasure.

Due to all these factors we’ve explored, the first PM ends up being a very expensive learning experience for both the PM and the company.

The company learns all the things they really need in a PM, and the things they really don’t. They can now confidently write a much more specific job description, and will be more precise in how they source, filter, and evaluate candidates.

Meanwhile, the first PM is likely feeling pretty burned out and frustrated. They fought many unwinnable battles, and in the end saw that they were never in a position to succeed. They may have even raised concerns during the interview about issues that ended up being foreshadowing of exactly what would go wrong.

This first PM has a short, challenging stint at a company on their resume, and leaves either saying “What if?” or “Glad I’m outta there.”

The second first PM then reaps all the benefits.

The glory of being the *second* 1st PM

Being the second 1st PM has all the benefits of being the first PM, but few of the drawbacks.

There are many reasons it’s fun and tempting to be that first PM:

  1. Prestige: It’s really cool to be the first product person in the door. You call many of the shots, you get to bring in process *your way*, and put your stamp on a product with some momentum.
  2. Equity: A good first PM can get a sizeable stock grant (0.2 – 1%) depending on pedigree and need, so the upside can be high.
  3. Challenge: If you like rolling up your sleeves and making something from (almost) nothing, this is an amazing role, with other awesome, hungry, hard working people to go with it.
  4. Growth: If the company succeeds and grows (which you play a key role in), you get to build a product organization, growing into a management track.

And unlike the *first* 1st PM, you are being hired with a much clearer picture of what they need; they’ll have learned from their mistakes the first time around.

This is why being the second 1st PM is one of the rare times it’s *not* a red flag that you’re applying for a role that is being back-filled.

In fact, it’s better than hearing it’s a brand new role, because you get some extra things that were created thanks to the efforts of the now departed first first PM:

  • Buy in: After what the other PM started, there is more support by the whole team and especially founders to make changes. They likely hired you specifically for skills and changes they now know they need.
  • Momentum: Chances are the first PM laid a foundation that gives the second 1st PM things to work with; they’ll have some analytics tracking set up, some semblance of project management, etc so you have the basic tools you need to do your job from Day 1.
  • Potential: The company is now a bit further along, a bit more traction, a few more key hires. So while you get the title, equity, responsibility, and opportunity, there’s a bit more certainty in the business so you can be confident in the opportunity.

I was a second 1st PM.

I’ve had a few friends go through being the first 1st PM and run into the challenges outlined, and once I heard their stories, I realized how much I benefited in being the *second* 1st PM at KISSmetrics:

  • Foundation: The first 1st PM had gotten us started on a number of key things I could pick up with: processes, customer lists, habits, etc.
  • Buy in: The team was experiencing a bunch of challenges as the 1st PM had left a few months earlier. They knew exactly what they needed this time, and were supportive of what I wanted to do from Day 1.
  • Opportunity: An amazing VP Sales had just come on, the business had hundreds of paying customers, Series A was raised, and it was clear what they needed and that I could run with it. I couldn’t ask for more.

At the time, I didn’t appreciate the battles that had already been won, and the buy in that I inherited.  Now, I do.

To all the first 1st PMs, who often don’t vest any equity, and found a huge difference between promises during recruiting versus reality, we salute you. It’s not a job for the faint of heart, but there’s another PM who greatly benefited from your hard work.

What if I’m interviewing to be a first PM?

If you’re interviewing at a company that is hiring their first product manager, be sure to ask if they’ve already had a 1st PM before.

Their answer will be very revealing, and helps dictate what you do next…

If you’re the second 1st PM

Dig into what the founders learned from the first PM. Find out why they think the other PM didn’t work out.

Look for signs that what they need is what you can do, and that they’re accountable to their side of what went wrong (or you may be set up to fail, too). The more thoughtful and introspective they are, and the more what they describe are things that you’re great at, the better your chance of success.

You also likely would benefit from networking your way to that first 1st PM. They likely know the skeletons in the closet and can give you an alternate perspective on the company. Then, you can work to discern the truth that is somewhere between what they and the founders tell you.

Not all previous PMs will want to talk, so if they decline speaking with you, respect their privacy. Instead, look for other ways to learn about the company like Glassdoor, asking others you may know there, etc.

Meanwhile, if you’re the first 1st PM

Go in with eyes wide open. Proceed with caution!

Unfortunately, no matter your optimism, or pre-existing relationship, there is a high chance you won’t work out.  Make sure it’s the right time in your career for the risk, you’re confident in the founder you’ll report to, and you can work from day 1 to iterate to what they need.

Once you’re there (or if you’re already the first 1st PM) a few things that can help:

  • Understand why you’re there: One of the biggest challenges of the 1st PM is turning a vaguely defined role and need into a clear cut set of goals you can achieve. Spending time with the founders to clarify everything can help you start on the right foot.
    • How to do it: Take another look at the job description and what you learned while interviewing. Talk with the founders to confirm what they need most, then deliver on those things as best you can.
  • Over-communicate: Building trust and confidence with the founder you report to is essential. You need to calibrate with them so they understand what you do and why, while also understanding their vision and expectations.
    • How to do it: Use 1 on 1s, weekly emails, get their feedback pre-launch, and give them access to the tools you use so they can see what’s happening.
  • Create a clear plan: Make a 30-60-90 day plan of what you are going to do, why you chose those things, and mutually agreed upon success metrics. This helps them understand how you think, and make sure you’re heading in a direction they agree with.
    • How to do it: A Google doc with bullet points is often all you need, and allows them to comment and ask questions easily. Then keep updating and reviewing it as you pass those monthly milestones.

There are definitely times where the 1st PM has worked out the first time, so it is possible. However, whatever vetting you typically do for a role, triple it before taking such a role, or even consider consulting as a way to try before you buy if you’re unsure.

Is a 1st PM role right for you?

Being a first PM can be a great way to learn quickly, level up your career, and work with amazing people. It can also turn into a short stint on your resume, cause burnout, and create deep feelings of frustration over what could have been.

If you’re thinking about becoming a first PM, realize it’s very different than just about any other product role you can have. Take your time, talk to others who have been 1st PMs, and make sure it’s what you really want.

Have you been a first PM? Please share your story in the comments so others can learn from your experience.


>>> Are you passionate about building great products & live in New York City?

I just moved to NY and am looking to connect with other people that love building great products to share tactics, fresh ideas, and cool products.

Interested? Reach out on Twitter (I’m @Evanish) and let’s get coffee.

Not in NY? Follow me on Twitter and let’s keep in touch there.

To New Beginnings: TCN Acquires Greenhorn Connect

Dear Boston,

5 short years ago, Ashkan Afkhami and I were sitting on Northeastern’s campus talking about Boston’s startup community and what could be done to help better organize everything it had to offer.

Not long after that, I found myself at the unConference at Sun Microsystem in Burlington listening to Scott Kirsner and Tim Rowe’s “TurboCharging the Entrepreneurial Culture in Massachusetts” session where they talked about how there needed to be a central place for all the resources and events in Boston’s tech scene. On that day, I nervously raised my hand declaring I wanted to take on that challenge.

That was the day Greenhorn Connect was born.

These last 5 years have been amazing. We’ve seen so much growth in the ecosystem and played a small part in making it better. We’ve helped many find jobs, connected thousands with the resources they need, and been a voice for the community.  I’m proud to have been part of making that a reality and honored to have had a great team and community partners help Greenhorn Connect thrive over the years.

From the beginning, I had the goal of Greenhorn Connect helping organize the Boston tech community and making it easier for newcomers 10 years after its start. Now, after 5 successful years of Greenhorn’s life, I realize that fresh ideas and new, local leadership can take Greenhorn Connect to places in the next 5 years I never could.

That’s why I’m excited to announce that TCN, The Capital Network, is acquiring Greenhorn Connect. Of all the organizations I spoke to about Greenhorn Connect, TCN had the best combination of resources and a shared vision for serving the Boston startup community. I am excited they’re taking the reigns to lead us into the second half of that goal.

Greenhorn Connect has always been resource constrained with our small, passionate team, and TCN will be able to alleviate some of that by mixing our team with theirs. Our teams have complementary skills and established relationships, which will enhance and grow both missions.

TCN is committed to continuing our current programming and building on what we’ve created. Expect to see our Student Dinners starting this fall and the Greenhorn Summit is very far along in planning for our annual fall event.

I want to thank Paul, Ariel, and Eric for being awesome throughout this process and I’m excited to see what they can do with TCN as the next chapter in Greenhorn’s history is written.

As for me, Tim Rowe told me once, “it takes as much effort to start something small as it does something big.” I’m excited to put that to the test as I set out on the next steps in my startup career.  I’m currently applying all that I learned in building, managing, and ultimately selling Greenhorn Connect to my next venture already in progress: Lighthouse, an app to help you be a better manager.

Thanks to everyone that has helped Greenhorn Connect along the way. This day would never have come without you.

Thanks,

Jason


 

PS: I’d like to call out in particular a handful of people that have been instrumental in Greenhorn Connect’s history.

To key supporters, Thank YOU

  • Scott Kirsner for giving us so much press and support over the years.
  • Tim Rowe for helpful advice and helping spark Greenhorn Connect with the MassTLC session with Scott.
  • Gus Weber for being the first sponsor of Greenhorn Connect. We wouldn’t be here today without the ongoing support we’ve received from Microsoft and it’s people like Walter Somol, Abby Fichtner, Sara Spalding, Betsy Aoki, and Cathy Wissink.
  • Greg Hoffmeister and Jon Frisch of T3 Advisors for being amazing supporters since our early days.
  • Microsoft has been an amazing host and sponsor to so many events including almost every event we’ve ever put on. The tech ecosystem is much stronger due to them.
  • David Ekelund for being Greenhorn’s startup lawyer who understood our needs and was always helpful.
  • Our many partners & sponsors along the way including: NEVCA, thoughtbot, Acquia, Grasshopper, the City of Boston and their 1in3 program, Cort & Jake for helping in the early days as they hustled on DartBoston, Wayfair, Carbonite, Sonos, Yesware, and so many others.

…and the team, THANK YOU

  • Ashkan Afkhami for being crazy enough to cofound with me on starting this business.
  • Pardees Safizadeh for being the first person to join our team and give us a real voice on social media for Greenhorn.
  • Ian Stanzyk for helping with our job board which was a key revenue stream during our history.
  • Paul Hlatky for rising to the occasion and doing a great job taking the reigns when I moved.
  • Angela Lei and Will Cox for being awesome team members as Paul took the reigns.
  • Ariel Winton and Eric Pasinski for being great team members today and going forward as we transition with TCN.

And finally, thank you to the community.

You all are awesome. It’s always been a blast serving this community and I appreciate all your support. I hope you’ll do the same for Sam and the TCN team.

The 2 Most Important Skills to Start Your Career

There is nothing harder than starting out or starting over. When you are new, it can be difficult to get your foot in the door and make a good impression. It can be hard to tell the difference between incompetence and a simple lack of experience.

Therefore, if you’re just starting out, there are two skills that are essential and will carry you farther than any others:

1) A Fierce Attention to Detail.

Any manager with a new hire has in the back of their mind the questions of, “Can they handle this?” and “How much do I need to keep an eye on their work?” If your manager knows you have an excellent eye for the details, they will be much more trusting in your abilities, knowing that you’ve taken good notes of their instructions, will triple check your work for careless mistakes and won’t do anything to make them look bad.  Building this trust can be the difference between a fast accelerating career with new responsibilities and languishing as an entry-level hire for years.

The longer I’ve been a manager and worked on product teams, the more I appreciate this trait. Over and over again we see the evidence of how the little details are what people notice and love (A great example is how Crashlytics built for Tweets which led to their viral growth). This is at the heart of great craftsmanship.

2) A Hunger to Learn.

Unfortunately, minding the details is not enough to succeed. You must also be eager to learn new skills. The faster you level up, the more likely you are to advance in your career whether always at the same company or at new ones. You need to learn from others and seek out sources of information on your own, which are skills in and of themselves to develop.

Many people in other careers have asked me how to get into product management, which isn’t always easy. However, one of the easiest ways to change your role is to work at a growing company and show how fast you can learn and grow.  This gives a company the confidence to give you more and new responsibilities.

The Combination is the Key.

When you combine an attention to detail with a hunger to learn, you will be unstoppable. Watching for the little details will make you more inquisitive and help you find the hidden gems and little secrets others gloss over. The little details are where life’s curiosities and greatest lessons lie.

As you grow the confidence of others and use curiosity to drive your learning, you will open new doors and build great relationships with others in your field. You are likely to attract great mentors who enjoy watching your development and love sharing stories and lessons to further your learning. They will also become your strongest advocates, either as great references, or the kinds of people that hire you again and again.

What do you think are the most important skills for those starting out?

Get Lighthouse
Want help developing great young talent? Managing new people for the first time and want to feed their hunger to learn and keep your own attention to detail?

Then sign up for Lighthouse, the app to help you be a better manager.

Building a network is about playing the long game

When I moved to San Francisco, in many ways I was totally starting over. After 8 years in Boston including 3 in its tech scene, I had built many great friendships and connections. I still keep in touch with many of them today, but being across the country is definitely not the same as having beers, dinners and coffees regularly.

I find nothing more fascinating than the challenges and struggles in building a company and how some succeed where so many others fail. I greatly value the insights into how companies are run and the tough decisions leaders face, so it was really disappointing to suddenly miss out on all those conversations I was often privy to in Boston. As I’ve worked to rebuild what I had in Boston, I’ve come to realize an important lesson:

Building a network is about playing the long game.

A number of my friends in Boston are now successful founders and C level leaders. Many are raising B and C rounds right now and two even sold to Twitter for a substantial sum. I’ve learned an immense amount in conversations with them and found their first hand accounts inspiring.

As much as I would love to know the same caliber of successful founders in the Valley right away, it’s unlikely to happen. Instead, what I can do is the same thing I unintentionally did in Boston: get to know people before their startup success. Some of the aforementioned founders I knew when they had just raised an angel round, others before they even started working on their ideas and were instead employees at other startups.

You don’t know Jack.

I hear many people try to get to know the big names in town or even pretend they already do because they talked to Ev or Jack or Zuck once at an event. When you think about the odds of them remembering you or answering your email (if you even have their contact info) it’s pretty slim.

…but you could know the next Jack.

Instead, focus on getting to know the talented people around you that will be successful. Find ways to be helpful for them (much more likely than you being able to help Zuck) and keep it all in perspective; over time you will grow and develop and so will your friends. Like a fine wine you’ll find your network gets better with age. Those same people will happily return your emails and provide assistance no matter how successful they become. They may even work with you on your next venture.

Does Boston Have Too Many Startups? A response to Kirsner’s Sunday Globe Article

This post originally appeared on Greenhorn Connect and has a boatload of comments. See here: https://greenhornconnect.com/blog/does-boston-have-too-many-startups-response-kirsner-s-sunday-globe-article

In the Sunday Globe this week, Scott Kirsner posed the question, “Does Boston Have Too Many Startups?”  The article seemed to try to make the argument that all our little startups should just be employees at bigger startups (disregarding how bigger startups, start out…).

The article is really best summed up in the quote in the article by Craig Driscoll, “companies that hope to grow need to do more than complain about how tight the talent market is.” I find it fitting that coincidentally, Ryan Durkin, COO of CampusLive (and mentee of Mr. Driscoll as a Highland Capital portfolio company) writes about attracting talent today:  http://www.ryandurkin.com/blog/2011/10/how-to-hire-dudes-showers-kitchens/

I’ve spoken with a number of friends about the article and had some interesting Twitter conversations as well and wanted to highlight some of the key points that came from them.  (Note: Kirsner sought out some thoughts which you can see on his Globe blog here.)

1) We don’t talk about logical career paths enough

Quick: explain, with examples, a logical career path for someone to evolve to be a successful entrepreneur.  Stumped? I know I am. Most examples I think of fit in the “Zuckerberg” files of folks who didn’t have much of a startup pedigree before launching their monster success (think Matt Lauzon, the many TechStars companies, etc).  I look at the titans of our community like David Cancel, Dharmesh Shah, Jeff Bussgang and know very little about “how they got here.”

It’s easy to tell people “go work for a startup first,” but you need to show them examples of people that have succeeded in doing that, and if you didn’t as a founder, then you have to acknowledge you have some hypocrisy on your hands.

2) We don’t have enough serial entrepreneurs and mafias

We are all familiar with the Paypal Mafia and some of the many startups the former employees spawned, but where are Boston’s Mafia’s? There was a great Bostinnovation series covering some of them, but it seems like there are fewer and certainly less celebrated.

These mafias are exactly what would convince someone to *join* a startup instead of start their own: join a team and have a great exit and then have peers and valuable experience to start another.  Maybe an offshoot of Eric Paley‘s Founder Dialogues needs to be “Mafia Dialogues” and bring in a few people from a successful team to share their combined story. We also need to think about whether it’s good for a CEO of a billion dollar company to be proud that all of his first 10 employees are still working at his now billion dollar company.

I think Rob Go was also on the right track highlighting the power team of Brian Balfour, Aaron White and Ariel Diaz teaming up for Boundless Learning (and also happens to talk about the importance of “more shots on goal,” not less startups as Kirsner suggests).

3) We don’t take enough chances on Greenhorns

I am very lucky. What few of you remember is that no one was interested in hiring me when I came into the tech scene. John Prendergast was the first to give me a small shot doing some work for him, which then led to the opportunity to pitch Laura and the oneforty team on joining them (John was on their board).  That was a 6 month journey to get that full time offer from oneforty.  If I didn’t live as lean as possible and have the luxury of a little savings, I may have never made it.

Just like our investors are often criticized for wanting too much traction before they invest, many of our companies only want to hire people that have done a role before.  I know too many young, eager people who want to work at startups, and yet there doesn’t seem to be many roles available to them.  I get asked about Janet Aronica, who I hired at oneforty, a few times a month it seems and the irony is, I doubt anyone else would have taken a chance on a young, eager talent coming from the low rungs of a PR firm.  I also look at Kristin Dziadul, who once made videos trying to get HubSpot’s attention and was smartly hired by Rob May and Backupify.

This is not to lump everyone together. Matt Lauzon and the Gemvara folks have taken chances, and I know Diane Hessan has been an awesome advocate for some of the truly hungry Gen Y folks. Unfortunately, the rest of the community hasn’t caught on yet.

4) We don’t take recruiting seriously

It bears repeating via Craig Driscoll, “companies that hope to grow need to do more than complain about how tight the talent market is.”  Vinod Khosla went as far as to say “New CEOs should spend 50% of their time recruiting.”  I’ve seen the aggressiveness of Sequoia firsthand as they held an event the night before Startup Bootcamp for their founders who were speaking to tell a bit of their stories, answer questions and meet people. I know Dropbox has spoken at at least 3 Boston area schools in the last 6 months.  How many schools have you spoken at in your own back yard?

Maybe we need an event or two to talk more about recruiting talent (One of my favorite events ever was a fireside chat with Akhil of MassChallenge and Paul English talking about recruiting).  I think it’s a competitive advantage for some companies while others throw money at it, but it certainly seems like it might help.  More awesome posts on the subject like Brian Balfour’s and David Cancel’s would help too.

5) Complaining about funded startups is an insult to entrepreneurs

The funding climate in Boston has improved, but it’s still hard to raise money.  As the opening to the Bloomberg TV show states, TechStars is more selective than Harvard. If you manage to raise money, that’s quite an accomplishment, as David Friend says in his message to Kirsner.  If you have an idea that goes far enough to funding, you have an at bat and need to go try to execute. The amount you’ll learn with your small team will be tremendous and put you in a great position to contribute to another company.

Now, living off of savings, is obviously a big risk and so if someone is risking financial ruin to keep their fledgling startup alive, it most likely makes sense to go work somewhere. Then again, the Valley wouldn’t have Airbnb if those guys weren’t relentless.

6) We need to clarify what a startup is

Wayfair is a $350Mn+ company. HubSpot has over 300 employees.  Are both of them still startups? Neither? I worked at E Ink when they went from about 90 employees to 165.  From my experience, the Dunbar number is very real.  The culture really started to shift at that point and more HR rules and regulations hit, not by choice, but out of necessity.  Few companies are really like Google and provide the independence and opportunities similar to startups, and even there, I don’t think you get the same thing.

I’ve heard about HubSpot’s education classes that try to teach some business and entrepreneurial lessons, but I have a feeling they’re the exception, not the rule. I also wonder how they’ll be able to maintain it as they grow further.

7) What motivates an entrepreneur or early stage employee?

Another great quote from Craig Driscoll on advising companies was, “They need to figure out how to recruit and create jobs that are attractive for entrepreneurial people.”  An entrepreneurial person cares much more about working with other smart people, having flexibility and independence in their role and a feeling of true contribution and influence in the big picture of what they do.

When I worked at E Ink, everyone looked forward to their quarterly meetings where Russ Wilcox explained the state of the company.  It lifted the covers on how the company was doing and especially during the wild ride that was the exploding popularity of the Kindle, you could feel everyone having a renewed sense of purpose after work as they were a part of the amazing opportunity to replace paper books with E Ink technology.  I think that same sentiment is happening now with Gemvara as Matt hammers home the vision to change jewelry and e commerce on the web.  Entrepreneurial employees want to be a part of something bigger than themselves, while feeling like they’re really making a contribution.

—-

I’m glad Scott brought this conversation out for discussion, but feel like it missed the mark on what really matters in this ecosystem developing.

Why I’m Starting a Company Now

As I’ve been out on this journey to start a company for a couple of months now, I’ve had plenty of time to reflect on why I’m starting a company now.  From my perspective it’s really the only choice that makes sense for me. The last few years of my life have been filled with preparation for this. Here’s why:

1) I have a zen financial outlook

– I have a sizeable warchest saved up that means I don’t need a salary for quite some time (a year +).  An incremental salary increase is not appealing to me; I have few wants/needs in life and don’t see it changing for the foreseeable future. One day, I’ll probably have a wife, kids and mortgage. That day, it will be a lot harder to bet it all on starting a company.

2) Customer development, homes

– For over a year at oneforty, I was eating, sleeping and breathing customer development. Before that, I did some consulting for John Prendergast cutting my teeth and learning from one of our local experts. I’ve since mentored at Lean Startup Machine events in NYC and Boston and wrote numerous posts about the topic (nothing helps you understand what you know like teaching/helping others).  All this adds up to making me feel like I’m the Kathy Griffin of CustDev (aka- I’m on the D List : P).

– I’m ready to take this knowledge and understanding and use it to crush a startup.  I’ve already used it to kill 4 ideas that have come up and am continuing the learning process, leveraging the knowledge of the greats in custdev (like @hnshah, @brantcooper and @pv).

– Any company I launch will be forged in the pits of lean startup-dom, which is much easier than bringing it into an existing company.  A wise friend recently said, “Culture is like concrete in that it hardens and is hard to change later.” That includes being a customer-centric company.

3) I’m going to be a recruiting machine

– One of my favorite things about being Greenhorn is the opportunity to sit at the intersection of so much cool stuff in our ecosystem. As part of sitting at this intersection, I hear from people that are unhappy at their current jobs or just ready for a change, companies that are waffling and what companies are growing or shrinking. All of these are huge opportunities as we all know that often the best talent never goes officially “on the market.”  Thus far, I’ve mainly been referring those people to friends’s startups, but I’m looking forward to the day I can talk to them about my startup and bring them in for an interview as well.

– All of this doesn’t even consider the platform I have with GreenhornConnect.com and beyond to reach a wide audience, not unlike Dharmesh is able to use OnStartups (although obviously at a much, much smaller scale than him).

4) It’s who you know…

– To be clear, I have yet to accomplish anything significant.  However, as Mark Suster and many others talk about dots and lines in determining investment (which means showing progress over time to build confidence in others investing in you), I’ve already made a few lines thanks to Greenhorn Connect and other activities in our community. This makes me less of an unknown when I reach out for advice, introductions or investment. I’ll still need to prove it with the startup I work on, but it certainly helps.

– While I’ve been meeting and talking with many of the awesome people in our community, I’ve also been curating a list to understand what everyone is an expert in. When someone says, “Let me know how I can help,” I always come back now with, “Ok, what are you best at? What the best thing I should ask you for help with?” I’m noting what they say so I can leverage their offers the best way possible. I can’t wait to leverage this as my startup needs help in everything from leadership to technical questions, customer development to culture and beyond.

5) Greenhorn is a mini-startup

– Few investors see a lot of value in the experience I’ve had in building GHC or from similar side projects according to friends I know (they just respect the traffic and influence) but most entrepreneurs seem to understand the value of learning on the fly from it. Similar to how Dharmesh experiments with OnStartups, GHC is my little playground.

– I’ve hired and fired, managed a paper-thin budget, found 6 unique revenue streams and learned a little project management along the way.  All of this with only a fraction of my attention for the majority of the time Greenhorn Connect has existed.  I am anxious to leverage the learnings on a full scale startup and continue to use it as a low-risk avenue to perform experiments.

6) The skills I have are for a founder, not an employee

– Early employees and founders need to be athletes. They need to be able to handle any job and roll with the punches that come with an early startup struggling to find product-market fit.  It helps as an employee to have a specialty that you can then grow into as the company hires more people and everyone gets more specialized.

– In my case, customer development is what I developed as a specialized skill.  One of the things I learned at the startup I worked at was that a founder needs to own customer development; the person doing customer development is the line of sight to the customer and it’s impossible to relay that perfectly to a management team (although I tried with detailed notes, summaries, email wrap ups, meetings, etc).

It’s never been a better time to be a young entrepreneur and I’m not that young (26). I feel like I have a combination of plenty of chips to bet and a through-the-roof risk tolerance right now. You are who you surround yourself with and most of my friends are founders or really early employees, so it only makes me more excited to be a founder as well.


Technical and working on something cool that you’d like some business help with? Drop me an email at evanish.j[at]gmail[dot]com and let’s talk. 

Fall Accelerator in Boston?

I’ve been helping a friend with his startup recently who shows a lot of promise: early (paying) customers, solid key elements of a product and a logical business model he’s validating.  He’s in a perfect position to join an accelerator and take his company to the next level. The combination of great mentors, a structured program to plan and move the business forward and modest financing represent the things he needs most right now.

Unfortunately, every accelerator program is done this year or currently going on. In fact, unless he had applied by May, he’d have been out of luck for all of 2011.

We have a number of great programs already in place, but they’re all in the spring and summer:

Spring: TechStars

Summer: MassChallenge, Summer at Highland, BetaSpring (Providence)

…but nothing for the Fall or Winter.

This leads me to a few questions:

What would you tell someone in his situation?

Can Boston add another accelerator?

Would TechStars go twice a year like it has in NYC?

Competition and Inspiration: Environmental Effects of Nantucket and Beyond

When I was a freshman in high school, my father and I attended the Cumberland Valley High School Track and Field banquet. It was an annual event to celebrate the end of another track season by looking back on the season, recognizing great contributors to the team and providing the coaches an opportunity to send off seniors and talk about plans for the future.

My freshman year, I was far from good. I barely made the team that traveled to away meets (they only took the top 5 for each event).  I only ran track that season because soccer hadn’t worked out in the fall and my parents wanted me to try another sport.  It helped that my father ran track when he was in college, which made me think I’d automatically be good at it. I was wrong.

It was a good enough season for a freshman as I enjoyed personal victories fending off challenges for that last spot for away meets and taking 25 seconds off my time (2:40 to 2:15).  However, in the grand scheme of things, no one but my parents and I noticed these “victories.”

At the banquet, our coach reflected on the conference championship we had won and the top athletes on the team that were returning the following year.  I watched from my seat as I felt envy for the high regard the top runners were given. I realized that for all the accomplishments I thought I’d had that season, they were really empty; I hadn’t scored a single point for the team and wasn’t even on the coaches radar as an “up and coming” runner.

As I was leaving the banquet, my long distance coach asked me if I would run cross country in the fall. He told me it would help make me a better runner for the next track season.  I agreed.

As I got in the car with my father to head home, I told him I was going to train all summer and do whatever it took to make varsity for Cross Country.  My father was supportive, but reminded that varsity meant one of the top 7 runners at the school. I had just finished a season where I was barely the 7th best runner on the team in one of a dozen different race lengths.

That summer, I ran over 620 miles in 3 months.  I built up to running 10 miles a day. Every day, my father would wake me up when he went to work and I would run 7.5 miles. An hour after dinner at night, I’d run 2.5 miles more.  During those 3 months, my mile pace went from 8:30 per mile for the 7.5 mile run down to 6:30 per mile for the 7.5 mile run.

To everyone’s surprise, I showed up in great shape at the start of the season and made the last varsity spot.  The hard work had paid off and now I was mentioned as an “up and coming” runner and had the respect of my peers. From there the work was just beginning, but I had made the leap necessary to work alongside the top athletes and take the steps necessary to eventually captain the Cross Country team my senior year.

Going to the Nantucket Conference last weekend felt like the Track and Field Banquet all over again.  Greenhorn Connect got me in the door, but it felt similar to just making the away squad to run the 800 meters; I’m as much a rookie (if not more so) as the other sponsored young entrepreneurs that attended.

Sitting here at the genesis stage of my next startup, I can’t help but feel the pressure to do something big and find a way to raise my game to hopefully work to one day be an equal of the more distinguished Nantucket attendees.  I have every intention of working just as hard on my next venture as I did that summer to make the varsity cross country team.

My thoughts on #BetterMA: How to Retain Gen Y

Yesterday was the “Cultivating Talent: A Building a Better Commonwealth Forum” at the beautifully restored Paramount Center. The goal of the event was to discuss how Massachusetts can better engage and retain Generation Y. While I was expecting a lot of rhetoric and empty conversation, I was pleasantly surprised that the majority of the event had very productive discussion and moved past stereotypes and un-actionable obstacles (sorry, the weather isn’t changing and neither are T hours).

Attendees were encouraged to share their ideas after the event via their blogs, so I’d like to share a few of my thoughts:

Give the “Stay Here” program a facelift.

During audience Q&A, I asked Governor Patrick about the program and suggested they get a better name ASAP.  As a Gen Y’er there are few things less appealing than the command, “Stay.”  We’re an aspirational group and like to think that we’re all blazing our own trails.   Phrases like “Stay Here” run counter to that as it feels like our parents asking us not to go or just a group begging us to do something we’re not interested in (one tongue-in-cheek audience member proposed the change, “baby, don’t go!”).

So what’s the solution? (as the Governor rightly put me on the spot for my suggestion)

I like “Grow Here”, but “Develop Here”, “Be Here” and “Build Here” all work too (note: because of the overarching Mass, It’s All Here program, it has to end in “Here”). The key to me is that the phrase should be inviting and encouraging; I want to know there’s a great party going on and I’d be a fool to miss it. I would also like to know that you understand Gen Y and know that graduating college is just the first step in a career filled with growth and opportunity.  “Stay here” feels like that needy girlfriend you dumped when you went to college. “Grow here” and “Be here” feels like that experience you had at that awesome party you found on the second day in college and never seemed to truly leave.

The Simplest Solution – Give Us Fulfilling Jobs.

Diane did a great job in pulling the panel back from a downward spiral into the same, unlikely-to-be-fixed issues that have plagued many similar events – T and bar hours, cultural complaints and high cost of housing.  She reminded everyone that young people regularly happily cram themselves like sardines into tiny, overpriced apartments in NYC.  If we’re happy with our work and our immediate environment, we’ll happily make sacrifices in other areas.

As reported recently in the New York Times, “the unemployment rate for 16- to 24-year-olds is a whopping 17.6 percent.” If you included the number of people who have jobs unrelated to their majors, but are waiting tables or doing temp work, the number would grow even larger.  I refuse to believe that 1 in 5 (or more) of my fellow Gen Y members is a total unemployable loser.  The fastest way to retain our local graduates is to give them challenging, interesting jobs.

We have to find a way for these better opportunities to be as visible to students as those stuffy, entry level, soul-sucking jobs at finance companies and other conglomo-corp type companies. As I wrote in my contribution to Kirsner’s Globe piece…we need to Go to Them!

Smaller, more interesting companies obviously have less bandwidth, but that just means you need to get creative.  Leverage your existing staff to start with the schools they went to; they’re likely to know how to get around some of the dead ends in the schools career services department; even Northaestern, (where I went) #1 in job placement after graduation, has an ineffective career services department…it’s the co-op program that gets everyone their jobs. So also think about getting an intern or two. They’ll be cheap and a great way to test a young person’s talent before you invest in a full time offer.

There is great complexity in the challenge of motivating and retaining an entire generation. These are just 2 areas I think we can immediately improve.

How would you improve things for Gen Y in Massachusetts?

Leadership Lessons First Time Entrepreneurs Forget

While building Greenhorn Connect, I’ve spent a great deal of my time with young and first time entrepreneurs.  If there’s one thing I’ve come to appreciate, it’s the absurd odds stacked against any of us succeeding; there’s just so much that you have no idea about and need to quickly learn.

You could spend years learning just one small subsection of your duties like SEO, analytics, customer development, copywriting, design, fundraising, product development, development architecture or simply great coding, but the demands of startups says you need to become competent and relatively adept at all of those and more.  Amongst all those hard skills, I didn’t even mention leadership, which I think is the most underrated skill to develop as a young entrepreneur.

Leadership is a bit different, because it’s a soft skill; it’s not as easy to measure as the success of your marketing campaign or the elegance and functionality of your code.  However, it’s an immensely important skill and one with more long term value than becoming an expert in any one of the aforementioned hard skill areas; if your goal is to build a company with more than yourself as an employee, then you’re going to be leading others.  As you grow, you’ll be leading more people and spending less time on any of the individual skills you used in the early days and much more on communication, vision and goal setting and coordination across teams.

As I’ve learned through my own errors and in talking to other young entrepreneurs, I’ve noticed there are 2 major concepts most of us don’t recognize that are absolutely critical to leading your team even when you only have one or two employees:

1) Your employees don’t work for you; You serve them.

Having employees means that you’ve been able to convince others to work with you on your idea.  Appreciate the incredible feat that it is.

However, do not think that because they work for you that they are now enlisted to your dictatorship. You need to involve them in core discussions, listen to their ideas and feedback and cultivate a culture of appreciation and shared passion.   A happy, engaged employee is 5x as productive as a frustrated, stymied or sad employee.  This ebbs and flows, so you really need to watch for it on a daily basis.

Showing appreciation for those that work for with you is not optional; you cannot over-recognize their best efforts.  At the same time, it is a balancing act.  There are times for the carrot and other times it is best to lead them with a stick.  Each employee will respond differently, so it’s a skill that requires fine tuning for everyone you work with.   Personally, as much as I love a good reward, I value constructive criticism significantly more; I’d much rather hear how I can do even better next time than dwell on what went right. Unfortunately, what I, you, or anyone else prefer is completely different than the next person you hire.

I constantly feel humbled by the fact that I have a team helping me make Greenhorn Connect a success today.  I do everything I can to make sure Pardees and Ian know that and have learned well the power of having excited, motivated people helping you fulfill your vision. An hour spent cultivating your employees will pay you back exponentially.

2) Uncover and fix problems when they’re small.

With all the hustle and constant activity buzzing around a startup, it’s easy to overlook small problems. Don’t.

When problems are small, solutions are small as well. When problems grow up, then it takes big, dramatic solutions to overcome them. If it’s an interpersonal issue or a major team issue, then suddenly that small issue can lead to someone having to be let go.

Catch problems when they’re small by reading your employees;  look at their face and posture, and if an employee seems down or upset…asking them if something is up and if you can help has huge immediate and long term benefits.

Conflicts and small issues are often simple misunderstandings or honest mistakes. Tackling them head on breeds a culture of accountability and openness to healthy criticism.  When you get your team in this habit, it becomes much easier to avoid major problems, because they never get that big.  Having a discussion about firing someone is a much more dramatic discussion than talking to an employee about a minor issue that may have caused conflict or hurt the company.  Nip problems in the bud and encourage your employees to do so as well.

This post may seem like stating the obvious, but theory and practice are two very different things.  Just like hard skills require practice and active use to become sharper, leadership skills like the issues above require active diligence to become adept at them. Ask yourself how your team is doing at managing these issues; I bet there’s times you’ve noticed your team’s mood affected productivity or a problem grew larger than it should have and caused trouble.

Have you learned these lessons the hard way? What key leadership skills do you think first time entrepreneurs need most?