Tag Archives: startups

Introducing the Practical Product Podcast

30 September 2022

Being a product manager is tough. No one majors in it, every company seems to want something different, and most learning comes by a combination of on the job trial & error, and reading blog posts.

Over the years, I’ve tried to share the most practical, actionable lessons I’ve learned from mentors and my own experiences. I hope a few of them have helped you along the way.

It’s also why I’m excited to share I’m starting a podcast with the same mission: teach others how to be great product managers.

The Practical Product Podcast

In the coming weeks and months, you’ll be hearing from many of the experts that helped me learn some of the most important skills I’ve written about here and tweeted. You’ll also hear from guests I’ve coached and gotten to know.

Each episode we’ll focus on a key challenge product managers face, or a skill they must master including topics like:

  • How to write a product spec your team members actually want to read.
  • What it’s like being a 1st Product Manager and pitfalls to avoid both as a CEO hiring them, and the Product Manager considering such a role.
  • How do you get your first 10 customers for a new product?
  • The broken hiring process for product management
  • Why feature voting apps are terrible and what to do instead.

…and much more.

Most importantly, we’re going to help you know exactly what to do, because what would “Practical Product” be if not all about putting what you hear into practice?

You can listen to our first, teaser episode here, and click the Subscribe button to find us on your favorite podcast platform so you never miss an episode:

Hear every episode as soon as they drop when you subscribe to the show on your favorite podcast platform here:

And for other podcasting platforms, you can find more links here: https://practicalproduct.transistor.fm/

Why you should read 100 books

26 January 2014

12 Comments

When I was fresh out of college with a internship at E Ink (maker’s of the display screen for the Amazon Kindle) I emailed the founder and then CEO, Russ Wilcox, to see if he would meet with me to give me some advice on entrepreneurship. Lucky for me, he was willing to schedule a meeting before my internship ended. You can read the full story here, but one of the best pieces of advice he gave me during our meeting was simple, yet powerful: Read 100 Books.

At the time it almost didn’t make sense and led to more questions than answers. What books? Why that many? How fast? By when?

I remember frantically writing down a bunch of book titles he started mentioning and then he stopped me and said the important thing was that they were on a diverse set of topics with different viewpoints instead of any specific books. He suggested trying to read 5-10 on categories like sales, marketing, leadership, negotiation, etc.

Mission Accomplished.

5 Years and 4 months after that conversation, I’ve finally hit the number and now looking back, I realize it’s one of the most important pieces of advice I ever received. I would not be where I am today if I hadn’t read as much as I have. Reading 100 books has done all the following for me:

  • Helped me better understand the responsibilities of coworkers (especially important as a product manager and startup founder).
  • Being comfortable in a conversation on just about any subject due to what I’ve read.
  • Rapidly improved my skills in key work responsibilities helping me accelerate my career and avoid costly mistakes.
  • Met other great people who also read regularly.
  • Given me the confidence and framework to help me learn anything.

If you’re reading this, I encourage you to also read 100 books. But realize it’s not about the number, but a routine of reading regularly that will serve you well throughout life.

Here’s my quick advice on how to make it happen and make the most of it:

1) Read what you can apply immediately.

I’ve managed to read a wide variety of books that have helped in my career and I’ve always chosen books based on what my current challenges and interests are. This has helped me apply concepts I pick up as I read a book, usually over the span of 2-4 weeks, depending on the length.

When I was moving to SF to run product at KISSmetrics, I started out with a great book on Product Management, then dove into a few books on design, before finding myself diving into sales, marketing, leadership and strategy books depending on what was happening at work and my personal life. Every time, I found great ways to build on what I read in my life around me which has helped tremendously with retention and understanding.

2) Get good recommendations.

Not all books are created equal. In fact, most books are pretty terrible, especially business books. There are gems out there though, so it really pays off to ask others who read what the *best* books are they’ve read on a subject. This has saved me tons of time on books that aren’t worth my time. This is why I made a list reviewing of all the books I’ve read  and some of my all time favorite books for entrepreneurs here. You’ll also occasionally find posts about books that CEOs like Jeff Bezos has his leaders read, which are usually great.

3) Build a routine of reading.

I read on public transportation. First it was riding the T in Boston and now MUNI around SF. I love this for so many reasons:

  • It gives you something to look forward to even when a bus commute might be lengthy.
  • A book won’t get stolen like your cell phone might be when you have it out as you play Angry Birds/check Facebook, etc.
  • It gives you bite size chunks of reading as most rides are 10-30 minutes…just enough for a chapter or two.
  • A book is a great way to get just a little bit more personal space on a crowded bus.
  • It’s a great warm up and cool down to your work day if you read during your commute.

If that’s not an option for you, build a routine around it in some other way. Maybe it’s 20 minutes before you go to bed, while you eat breakfast or perhaps audio books while you drive to work. It is the routine of always reading something that will carry you through that many books over the years.

4) Carry your book around with you.

Nothing sparks a conversation like someone noticing what you’re reading. Often those that notice read a lot too, which is a great way to make friends and you can get more recommendations for books from them. This also means that if a friend is running late, you always have a productive way to fill the time.  I brought Dale Carnegie’s “How to Win Friends and Influence People” with me to Bootstrap Live and ended up talking with Andrew Warner and the guy next to me about how much we all loved it.

5) Write all over your books.

Despite working in technology, I still prefer physical books in my hand. I underline, I highlight and dog ear all my books. Something about it helps me with retention of what I read. Even if you prefer to read on a tablet or Kindle, be sure to take notes and challenge yourself to think about how to apply what you’re reading. It helps a lot to review books you’ve read before when you have that subject come up. It’s amazing to me how often past events line up as examples (or counter-examples) of something I’m reading. I’m always sure to take a moment to consider it and write it down in the book.

6) Always make progress.

Life doesn’t always go as hoped or planned. There are times of frustration and stagnancy both personally and professionally in all our lives.  I’ve found one of the best things for me is knowing that no matter what is happening in my life I’m always learning because of what I’m reading. I can always look back and see progress there.

It has also helped that when I’ve had down times, if I read something related to it like a book on happiness or successfully navigating your 20s, I’m actually being proactive about the problem and getting advice from someone great who took the time to research and write a book about the subject.
—

Remember, this is not a race. The point of reading all these books is to absorb all the ideas and skills shared in the books, not race to the end.

I’ve heard some people like to skim books and think that doing things like reading the opening and closing paragraphs of a chapter and reading headlines in the chapter is enough. They’re either reading the wrong books or missing out on some deep lessons.

As a wise man once said, “Anything worth doing is worth doing well.” It is the journey to 100 books that I both enjoyed and grew tremendously from…not the milestone of specifically 100 that matters to me; I haven’t stopped reading and won’t anytime soon. My Amazon Wishlist is longer than ever (please suggest the best books you’ve read in the comments!) and I can’t wait to learn through more great books for the rest of my life.

Why the Mayday button is another genius move by Bezos and Amazon

14 November 2013

Amazon recently launched the Mayday feature with a television ad campaign showing a one button press for help from a live person who can control and guide you through the use of your Kindle Fire HDX. If you haven’t seen the ads, here are a few of them:

At first my techie self said “why would anyone want that?!?” Then I realized Bezos’s genius.

Mayday isn’t for you.

If you’re reading this, you probably work in startups or technology. Since we are already well served by the iPad and various full-Android tablets, Bezos is targeting the technology laggards of the tablet adoption curve. These are people that want a proven product and only buy once the market is commoditized and discounted. They don’t care about the millions of apps that Apple has as they will only use it for a handful of key applications. They also don’t see the need to pay the Apple premium price either, so a sub-$300 Kindle Fire fits well.

Instead, these users are more like some of my older relatives who use their tablets for email, Facebook, browsing the web and watching videos, often as a second screen. These users sometimes struggle learning new technology and can be sensitive to asking for help as they are worried about feeling dumb.

Mayday is the perfect name.

Do you know what “Mayday” means? If you’re under 25 I wouldn’t expect you to. Anyone in the Baby Boomer or older generation will distinctly recognize it and understand its meaning as a universal call for help. It’s also way catchier than just another “Help” button and probably even trademark-able. Given the target of helping those less tech savvy who have likely not adopted a technology yet, it should immediately click with them.

Amazon isn’t in the tablet business.

I wondered: how could Amazon afford to do this on such a commoditized device where their margins must be slim? Then I remember this is Amazon. They’re not in the tablet business; they’re in the e-commerce business.

We know that e-reader Kindle owners dramatically increase their purchasing with Amazon (50-100%). I bet by now they know the LTV of Fire owners and realized they could afford the support because of all the ancillary spending they would get from those owners and opportunities to redirect users to Amazon solutions when they ask questions. Add to this the data they get on Fire owners knowing all of their activity and the optional ads special offers people can accept, and there’s a lot of value in getting a new Fire owner.

Amazon had to shake things up.

Amazon’s tablet market share is reportedly down significantly (21% in July 2012 vs 10% in July 2013). They needed to use a Blue Ocean Strategy to differentiate and find a unique part of the market they could win. Combining the Mayday button (to attract the hard to attract laggards) with some very obvious use cases (the family accounts with ability to limit access and a child’s time spent on the device) very specifically tries to carve out a strong niche for Amazon. If it works, the difference in cost structure for Amazon, the e-commerce company, versus other tablet makers will make it hard for others to duplicate the Mayday button.

Bezos continues to show he is one of the best strategist CEOs on the planet. Mayday is just one more move to capture value from an under served group and move them into the world of Amazon purchases.

The Unscientific Causes and Cure to Burnout

11 July 2013

12 Comments

Having recently burned myself out, it feels like it’s the unspoken condition plaguing those working in startups. It’s as debilitating to us as a torn ACL to a pro athlete, but is hard to recognize on the surface and not something you go to the doctor for. My hope is to help you and your team either avoid getting burnt out like I am, or if you are burnt out, help you understand the causes and how to bounce back.

Burnout != Tired

For starters, it’s important to understand this distinction. I’ve been plenty tired before. The kind of tired where you sleep all weekend or you skip an early morning class or meeting because sleep seems more important. In college, I would go with only 20 hours of sleep in a week during midterms or finals where I would be known to duck out of a classroom to do pushups to stay awake (yes, in retrospect, stupid). I continued similar behavior after college when working on my own startups or on the job, but after a good night or two’s sleep I was always ready for more.

Unlike those times, over the past couple of months I fell off the cliff into burnout. I managed to both physically and mentally exhaust myself in a way I never experienced before. So what was the difference? 

What causes burnout?

Simply put, it’s all about Passion.

When you do things you love and are passionate about, they actually renew you instead of taking energy. The problem emerges when that passion you feed on declines and work starts actually feeling like work. This quickly starts a death spiral as you need more and more energy to perform at the same level you’re accustomed. When you use up all of your reserves, you will find yourself burnt out.

As I was on the way down to burnout, this quote from Steve Jobs’s commencement speech really started to hit home:

“If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.

It’s important to understand why you would wake up and feel that way. The things most likely to make you feel that way include: (See more on this MayoClinc article on burnout)

  • Your work not feeling important
  • Lack of recognition for your efforts
  • Not seeing the results of your efforts
  • Not working on things you’re excited about
  • Lack of real progress being made on your projects
  • Repeatedly clashing with a coworker, manager or leader
  • A shift in your company’s culture that is unappealing to you
  • Misalignment between your values and the ones exhibited by your employer
  • Feeling like you have no control over your work (i.e.- lack of independence/decision making ability)

If you’re an employer/founder, take a good look at that list. Anyone who you think would answer Yes to more than one of those items is at risk for burnout or leaving your company.

How do you overcome burnout?

After admitting that I was really burnt out, I started talking to a lot of people about it and found that a surprising number of people had experienced it. Thanks to their advice, I learned a lot about how to recover (an ongoing process for me now):

  • Travel: Getting out of your current environment and just enjoying a place you visit can do a lot to recharge you. One friend told me the founder he worked for spent a month on a secluded island in the Caribbean after a stressful acquisition process and “never felt more revitalized” when he returned. The location doesn’t matter as much as the removal of stress and normal day-to-day duties and triggers.
  • Turn off technology: All our apps, social media accounts and email draw energy from us one small bite at a time. Every person I talked to mentioned the importance of turning off push notifications and rationing exposure to these attention-demanding items to really rest the mind.
  • Write down things that really matter to you: It’s easy to never make time to think about big ideas that matter to you. When I spent a week in Santa Monica, I spent a day each on questions like, “What are my personal values?”, “What’s most important to me personally?” and “What do I want professionally?” These can often reveal mismatches in your life that may have led to your burnout and reveal what you should do next.
  • Be ok doing *nothing*: As a confessed workaholic, this was really hard. I love feeling productive and that I accomplished a lot every day. To recover though, you need to let your brain rest, which means doing things like going for a walk or sitting in nature with no purpose in mind. (Joel of Buffer’s nightly walk is a great example of a way to maintain your energy levels)
  • Be honest with yourself and others: For about a month at my job I was in denial of what was happening. I actually pushed myself harder at first and then thought if I eased up a little it would be ok. Both only made it worse. Having now had a few weeks to truly recover and been honest with people has helped tremendously; people are much more understanding of slow responses and postponed meetings when they know why (and can sometimes even help).
  • Confront the problem(s): Often, the trigger for all those feelings that send you on your way to burnout are related to a person or a part of your environment. You absolutely have to bring change to things that are causing the stress or no amount of travel and rest will matter. One of my friends who helped with this post was able to save a strained relationship by finally having a tough conversation on how he and one of his cofounders communicated.
  • Don’t be afraid to move on: If you are unable to confront and resolve the causes of your stressful environment that caused the burnout in the first place, it is best to move on. Lingering will only burn you out further, lengthening the necessary recovery time. It can be scary to consider doing anything but what you’re currently doing, but admitting it’s an option and thinking about what you’d do instead may very well be the push you need to make a choice that’s best for everyone.
  • Realize it’s a marathon: Unfortunately, you don’t wake up one morning and you’re no longer burnt out. Instead, you feel a little better or worse every day depending on how well you’ve taken care of yourself. Use the recovery process as a way to build healthier ongoing habits and watch for the triggers that got you there in the first place so you never return. Most people told me recovery is measured in months not days or weeks.

Why do people let themselves get burnt out?

If you’ve never burnt yourself out, consider yourself lucky. You may wonder why people didn’t do something about this before fully burning out. There are a lot of reasons, but the ones I heard most commonly were:

  • Pride: “I’ll be fine. I always come through.”
  • Money: “The money’s so good, how can I quit this job even if I don’t *love* it?”
  • Loyalty: “I can’t quit. I’d let down [investors, cofounder, manager, teammates].”
  • Denial: “This is nothing. It will pass and I’ll be fine. I just need a good night’s sleep.”
  • Fear: “What would I do if I left?”

This is where you, the manager, founder or friend comes in; sometimes people need help realizing (or admitting) what’s going on. Recognize this and help them resolve it whether they need a vacation, a different role in the company or it’s time for them to move on.

—-

Why did I write this?

There’s been a lot written on burnout, but I felt like no one really boiled it down to its common, core elements. Hopefully some aspect of this is helpful for you, a friend, a coworker or your team whether you’re avoiding burnout or dealing with it already.

There’s a lot more to be said about burnout, so I hope you can share your experiences and great links to more on the subject in the comments.

Further Reading:

In my process of researching burnout, I came across some helpful links that are worth reading if you have additional interest in the subject (I’ll add any others you share in the comments):

Founders: You don’t own your employees

14 April 2013

12 Comments

[Ed. note: This is in response to a post by David Hauser entitled, “The Startup Side Project Bubble” which you can read here: http://buff.ly/10Lw9ek]

So many founders forget something simple: You do not own your employees.

They are human beings with their own passions, interests and lives. You have a vision of a reality you want to create. After much labor and hard work to get it off the ground, either funding or your own revenue allows you to hire help. Those people are choosing to devote a significant portion of their lives to your cause to help make it possible. Take a moment to appreciate that. 

In David’s post he argues that employees having side projects is bad for them and his business. This is so backwards.

First, telling someone what they should and shouldn’t do in their free time is a tremendous insult to them and their personal judgment.  It’s also incredibly short-sighted.

You want employees with side projects.

Especially for the creators at a startup (ie- the people that design and build your product), there is tremendous benefit to them having side projects. A few of those benefits are:

  • Experimentation. An outlet to experiment with new technologies before suggesting the company use them; no amount of research compares to having used a new framework and being able to provide first person accounts of the tradeoffs.
  • Independence. A place where they can make all the decisions (for better and worse) versus the negotiations that often happen in a company. You can also call this their creative release.
  • Mastery. The ability to further hone skills in a self-directed fashion, getting them to the 10,000 hours to mastery faster than standard work hours alone would provide.
  • Relief. Providing some variety in their life’s work can help avoid the burnout that comes from only working on one thing for too long.
  • Focus. Motivating them to get their work done efficiently because they don’t have every hour of the day to work on it. The saying goes, “If you want something done, ask a busy person” for a reason.
  • Contribute. The ability to help the greater tech community through contributions to open source projects, which wouldn’t exist without many people having side projects.
  • Network. They’ll often work with people outside their day job on these side projects, which will grow their learning and network. It might even provide the next recruit when you need more help at your startup.

And I’m sure there are others.

Great employees are a package deal.

In the early days of a startup, you want athletes, which are often entrepreneurs themselves.  Later, you want specialists who have deep expertise in their skills. By their nature the same skills you value each day in either group’s work for you also lends itself to having these side projects: In early employees that means a breadth of knowledge, while later, the depth of knowledge that comes from side projects is what makes many great later stage startup employees.

I would not be running product at KISSmetrics if I had only put my head down and worked on my past jobs (I wouldn’t even be in tech now most likely…I have a degree in Electrical Engineering). The skills that are core to my job came from side projects like Greenhorn Connect, taking the time to learn new skills in my free time and reading voraciously. Every founder wants to hire people with passion for their craft and a wide range or depth of skills.  This is a package deal.

“Why don’t you quit your job already?”

Taking a step back and looking at David’s argument, it seems centered around the idea that if an employee has a side project, they should quit their job immediately and start a company. While they should definitely quit their job if they’re ready to make a run at it as a business, they may not do that right away because of a few reasons:

  • Funding. They lack the personal funds and see the foolishness in fundraising when they don’t even know whether an idea has legs whatsoever.  Not all side projects have clear paths to revenue/bootstrapping either.
  • Motivation. Many side projects are for fun and passion. Sometimes those become businesses worthy of full time attention, but usually they are just an enjoyable thing to do with only part of their time.
  • Stability. Depending on what else is happening in their life, it may not be the time to start a company. If they’re getting married, just moved to a new city or a close family member is on their deathbed, they may not want the upheaval of launching a startup on top of that.

None of these reasons prevent a person from being a valuable contributor to your startup. In fact, someone may work for your company and add tremendous value you’d otherwise never receive.

This is a seller’s market.

If you have hard to find skills like design, product management or engineering, it’s a great time to be a startup employee. Companies must compete for you. With salaries skyrocketing, it takes more than money to attract talent. Having a good culture, treating people well and supporting them as individuals become important factors as well.

David’s views may work for him, but I caution other founders from adopting his cynical attitude towards those with side projects. The potential gains far outweigh any losses in hours David seems so concerned with and run the risk of turning off potential great team members.

How to Become a Better Leader Instantly

28 February 2013

2 Comments

Whether building a career at a large company or starting your own, if you want to advance and grow, soft skills like leadership are just as important to develop as hard skills like programming languages and sales tactics. Despite being a species evolved to live and work in groups, most of us struggle to effectively communicate with and motivate others. This is unfortunate, given how important and helpful a skill it is to master.

I’ve been studying leadership for a while and there are many techniques for motivating and effectively working with others. Many take some practice and skill. Fortunately, there are a few things you can do to very quickly develop your skills, which I was reminded of as I was recently reading the excellent book, “Fierce Conversations: Achieving Success in Work and Life One Conversation at a Time.”

One tip in particular stood out as something I’d heard many times before and I realized it’s the single easiest, yet important tactic to learn:

Give specific praise regularly

Animal trainers around the world know the best way to train animals is through rewarding good behavior. Just think about the last time you were at Sea World and the seals and dolphins got fish and other treats after each trick they did.

While humans are much more complex creatures, we still like rewards, just often in a different form: praise. Because this praise is written or verbal, the key is to be specific.  Don’t just say, “Good Job.” Instead, you’ll want to pull out exactly what was good so they know to do it again. Some simple examples could be:

  • “Great work on the folder feature, Susan. I really like how you made your code clean and easy to follow with comments explaining each section of the code.”
  • “Your report on quarterly earnings was great, Tom. Your graphics were perfect for explaining to the board how we recovered from the rough month.”

After praise like that, I guarantee you that Susan will continue to comment her code and keep it clean and Tom is much more likely to keep investing time to make great graphics for his reports.

This type of praise is powerful for a few reasons:

1) People want to feel appreciated.

Assuming you like your job even a little bit, you want to do good work. There are parts where you’ll put in extra effort. People just want to be recognized for that hard work and that will motivate them to do more of it. Think back to a time someone thanked you for a great job on a project you slaved over for weeks. Give others that feeling.

2) The absence of praise will be felt.

When someone does subpar work and you give no praise, they will notice and want to work harder to seek your praise they previously enjoyed. On the other hand, if you don’t praise people regularly, they are less likely to continue to put in the extra effort on projects. We have all had those moments where we went the extra mile on something and were disappointed when no one noticed. Chances are, you didn’t do it again for that boss or coworker. Don’t be that kind of manager.

3) People want to be noticed.

Especially in the startup world, it’s easy to take great work from your team for granted. Everyone just ships feature after feature, marketing content over more content and keeps grinding. This is also why celebrating wins as a team matters; it’s an opportunity to recognize both the collective efforts of the team and specifically who made major efforts to help the team get there. This is the key to making people feel like they’re “part of something bigger” that draws so many to the lower pay and longer hours of startup life.

Can you remember the last time you praised each member of your team? Were you specific with them or just a vague, “Good job”?

—

This is just one of the awesome tactics you’ll learn in the book, Fierce Conversations. It covers many excellent topics and will help you understand how to have productive and often difficult conversations effectively with others in both your personal and professional life. I scored it a 9 out of 10 on my ratings scale and highly recommend it.

The Fallacy of Chasing Startup Ideas

3 October 2012

3 Comments

Over the past week, I’ve caught up with a few friends that are in the process of searching for their next startup idea. One is an EIR, another a founder looking for a new idea for their startup. Less than a year ago, I was on a similar quest.  As much as the passion to build a company is a noble cause and one I deeply relate to, I don’t think you can find it by broadly searching for the right idea.

I believe there are only 2 ways to find a great startup idea: Experience and Passion

1) Experience

You’ve worked in an industry for years. You know all the inefficiencies in the market and how terrible the existing solutions are. You are the target customer or you know them because of regular interactions.  Because of your experience you have the connections to land your first customers with relative ease and likely already know what the Minimum Viable Product would be.

2) Passion

You may not know the industry well, but you’re so fired up about the idea you can’t sleep at night. You want this solution to exist, you know the world is not complete without it and you’ll run through walls to make it happen. This fire also is likely to give you a level of understanding of the end user that will translate to a great product you want to use.

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So which is more important?

If you’re starting a B2B startup, Experience is more important as it will help with those key early sales. For consumer startups, Passion is more important, since often new tactics are needed that industry experience would not help as they’d be outdated.  Ideally, you’ll have both as it will help get your venture off on the right foot and have the wherewithal to survive the trough of sorrow.

The problem I found in searching for a startup idea for 9 months and what I think my friends will struggle with is that without Passion for an industry nor Experience within it, you’ll be unlikely to magically come up with an idea on your own. If you’re really determined to start a company despite this, then your best bet is to find a founder to co-found with who has Passion or Experience (the best startups have both) or join a company you can learn a lot from in a high impact position(what I did by joining KISSmetrics to run product).

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

18 October 2011

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.

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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.

Fall Accelerator in Boston?

13 July 2011

3 Comments

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?

Leadership Lessons First Time Entrepreneurs Forget

7 June 2011

1 Comment

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.

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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?