It Started with Eight

Along with our friends at Alpha Edison, Flybridge and XFactor are excited to have helped create the #StartWithEight initiative.  #StartWithEight is a simple commitment – take meetings with 8 women from outside your networks in the month of March – with an ambitious goal – to build parity across the venture ecosystem.  

On some dimensions the idea that meeting with eight women outside your network could change the diversity of the venture ecosystem seems crazy, but my personal story would suggest it’s not.  For me, Eight led to 25,000 which led back to Eight, which led to more than 60% and over 700, which has resulted to date in 17.

I #StartedWithEight in November of 2016 when I joined up with Anna Palmer, the Co-Founder and CEO of Fashion Project, and more recently, Wondermile, my partner Kate Castle and 6 other women to launch SuitUp, a grassroots organization focused on identifying concrete solutions to issues women confront in their communities.  We built a network of over 25,000 women and those conversations resulted in a 100 Day Plan for Women, but also brought into sharp relief for me just how screwed up the funding dynamics are in the venture ecosystem.  

So those 25,000 led to another Eight, when Anna, Kate and I, in partnership with the entire Flybridge team, took an idea from the 100 Day Plan for Women and created XFactor Ventures with an amazing team of eight other partners, all of whom are female founders of venture backed companies.  Notably – more than half of the XFactor team were not women “in our network” prior to starting XFactor.   

One of the questions I somewhat naively wondered about prior to launching XFactor was would we see enough investment opportunities, as prior to the launch female founders made up only 10% of my personal “opportunity flow”, a fact I typically rationalized to being a result of my primary investment focus on B2B software companies.  But as we noted in our #StartWithEight medium post, “Startup land is a network-driven place”, and changing your network can have powerful results.  

For me the powerful results of #StartingWithEight are an “opportunity flow” that has transformed from 90/10 male/female to more than 60% female, well over 700 new investment opportunities I would not likely have seen otherwise, and 17 new investments.  

For everyone joining #StartWithEight this month, thank you for your support and commitment.  It has been amazing to see our friends in the venture community sign onto this initiative including 8VC, Accomplice, Bain Capital Ventures, Cosimo Ventures, First Star Ventures, G20 Ventures, Material Impact, New England Venture Capital Association, Pillar, Rethink Education, Rethink Impact, TenOneTen, Tectonic Ventures, Canaan Partners, Fika Ventures, Foundry Group , Genuine VC, Glasswing Ventures, Brilliant Ventures and The Engine.  You never know where it will take you, but it will be someplace good, someplace more diverse, and through that diversity, more effective.  If you are interested in adding your firm or company’s voice as a committed signatory to #StartWithEight, contact us at

As for us, we are #NotStoppingWithEight and feel like we are just getting started.  So we welcome more suggestions for amazing founders, joiners, advisors, board members, investors and potential investment partners from your networks with whom we should meet.  


From DIY to DIFM — Getting the Help You Need, When You Need It

I’ll be the first to admit, there’s nothing better than taking on a do-it-yourself (DIY) project.  I love a challenge and figuring out how to build or fix something can be exhilarating.  The reality of DIY, however, is that at some point you get stuck and the project switches from fun to frustrating.  Stuck and frustrated, I often find myself desperately looking for the “phone a friend” lifeline.  Sound familiar?

Over the past 15+ years, we’ve seen a boom in the number of companies focused on providing DIY technology platforms.  Constant Contact led the movement and has been followed by hundreds of companies that allow people to quickly, easily and cost-effectively deploy web-based products, services and marketing programs without having to spend thousands of dollars and months of development time. And while platforms like WordPress, Squarespace and HubSpot have enabled millions of small and medium sized companies to start and grow their businesses, the reality is that expertise cannot be 100% automated away and even the easiest to use DIY web platforms often leave end users stuck and looking for a DIFM (do-it-for-me) lifeline.

This is why I am so excited to be working with the Lorem team.  I first met Sam and Charlie during Mentor Madness week at the beginning of the most recent TechStars Boston program.  They were two young, smart, scrappy entrepreneurs who had identified and were tackling a problem where there were surprisingly few solutions.  In today’s “on-demand’ world you can get food, car rides, groceries, dog walking and most anything else instantaneously, getting true real-time help when your web platform fails is not really an option.


I left that initial meeting excited, instinctively feeling that Sam and Charlie were onto something and so, along with the rest of the Flybridge team, we dug in.  

First, we used the product and became a customer.  It was not supposed to happen this way, but one day all the content on a WordPress website we run to provide students with funding to attend industry events ( disappeared.  Kate, our exceptional Marketing Partner, spent an entire day banging her head against a wall trying to fix the site herself.  Not her area of expertise and time far better spent working with our portfolio companies or generating visibility for the firm.  This coincided with the visit from the Lorem team, so off we went.  One plugin download and a click of a button and she was connected to a Lorem expert.  The expert took a look at the problem, found multiple issues on the site caused by using out of date versions of WordPress and various plug ins, quoted $40 to fix it and within an hour, we were back up and running.  Kate became the first convert on the Flybridge team, calling Lorem her new “secret weapon” for website fixes.

Second, we scoped and sized the market.  The trend towards DIY platforms was not the question (WordPress alone powers 75 million sites), but competing alternative solutions were.  Simply, we saw two options for customers:

  1. Keep doing it yourself: This has the lowest perceived cost, but that is deceptive as trying and failing, hitting up Google searches and accessing the online support provided by the platforms is wildly time intensive.  This is what Kate first tried and it takes a business owner’s time away from running their business, it is frustrating and leads to a high-rate of dissatisfaction with the DIY platforms (read churn!) and it increases the cost of customer support for the DIY platforms.
  2. Find someone to do it for you.  The logical alternative and there are obviously lots of design and development firms and freelancers with the right expertise.  But none of them are easily accessible for small projects as on existing freelance marketplaces it can take days or weeks to define and execute a project and often with less trusted resources and design and development firms are expensive, charging rates of up to $300 an hour, and not geared up to handle small projects.

None of these options provide instant help when a company needs it and we agreed with the Lorem team that there is an opportunity to provide businesses with trusted, on-demand, in context, quick solutions at an affordable price.  

And then I did the math.  Who wouldn’t pay between $10 to $100 for real-time quick fixes on their website or other DIY tools? With nearly 30 million small businesses in the U.S. alone and Lorem quickly seeing these companies use the platform for multiple jobs and spending $400 a year on average, the market suddenly got much bigger than you would think.

The more I thought about the opportunity and met with Sam and Charlie, the more I fell in love.  As TechStars demo day approached, we knew we wanted to be a lead investor with the company.  At 6:00 a.m. on the morning of demo day, I emailed the team what was their first of several term sheets and we ultimately led a $1.1M seed round in the company along with our friends at Founder Collective (David Frankel) and a few angels including Randy Parker (Founder of Constant Contact) and Fred Townes (author of one of the most popular WordPress plugins called W3 Total Cache).

I could not be more thrilled to be in business with this talented team and look forward to being part of their success.  

Fired Up By a Flybridge Family Reunion


Last week there was an interesting piece of news in the tech world when Firebase/Google acquired the Fabric product line and team from Twitter. Over 20+ years in the venture industry and hundreds of companies, this was a first for me: two companies we had invested in merged post their respective acquisitions by larger players. While it was unusual, nothing could make me happier than to see Crashlytics, which was acquired by Twitter in 2013, and Firebase, which was acquired by Google in 2014, join forces and continue the missions they held from their founding, and our original seed investments, of improving the lives and effectiveness of mobile developers. Huge congrats to Andrew, James, Jeff and Wayne and many thanks to both Twitter and Google for their support of both companies and allowing them to deliver on their common goals.

Rewind the clock to 2011. At the time my core investment focus was on developer-driven cloud platforms and an insight that companies that went to market with products that delighted developers could achieve significant adoption and break down many of the barriers seen by companies that focused on more traditional enterprise sales models. Within this broader theme (that also led to our investments in companies such as MongoDB, Stormpath and Apiary), it was clear at that time that the mobile developer was the new rock-star and thought leader and that most new application development spend was for mobile apps. But while mobile developers were leading the way, it was still too hard and technically challenging to quickly and easily get high quality apps into the market. Over the next year, this thesis led us to make seed investments behind two phenomenal teams. Both companies started out focused on very different markets – Crashlytics on crash reporting and Firebase on a platform to allow developers to easily build serverless back-end platforms. But both had a common goal of creating innovative technologies to help developers create amazing apps.

It’s always interesting to look back on your investment successes to see what if any common traits they shared. For Firebase and Crashlytics, there were many:

  • Founded by young, passionate entrepreneurs[i] who had strong technology backgrounds, startup experience and an innate understanding of their target customer who were
  • Creating platforms that addressed large and expanding markets with a
  • Special “developer first” approach to working with the developer community that led to rapid adoption of their platforms which led them to
  • Blow away their seed round metrics within less than a year and in turn raise Series A Rounds led by their initial investors and ultimately to being
  • Acquired by leading technology companies less than a year after Series A rounds and these
  • Acquirers provided significant incremental resources, let the teams run independently and continue to innovate under their own brands post the acquisitions

I could not be more proud of both of these teams. With millions of apps and hundreds of thousands of developers now using their technologies, what each has built is exceptional and I am 100% sure, will only get better as they join forces.

[i] It should also be noted in this time of anti-immigrant sentiment that in each company one of founders was born outside the US

Post Election Advice

img_0404Flybridge held our CEO UnSummit earlier today for all the leaders of our portfolio companies.  It was a fabulous day and full of energy, and we will be posting more on some of the many insights these phenomenal leaders had about their companies and best practices.

But today is about a more timely issue, namely the election.  It was obviously the elephant in the room at the CEO UnSummit and I spoke to that directly in my introductory remarks. I have pasted in below what I said in the event it is of interest more broadly.

My intro remarks certainly took a different turn early Wednesday morning around 3am, so before we talk further about today I thought I would take a few moments to talk about the elephant in the room, especially as many of you have asked for thoughts on what the election means for all of us.

While I am no means a political expert, I have lived through many cycles in my 22 years as a venture capitalist and have a few thoughts on managing a company through uncertain times. The first and most important observation is not to panic. If you were excited about your market opportunity and the strategy you and your team are executing on Monday, you should be excited about it today. The big technology and macro market shifts that drive the markets we are all participating in tend to meaningfully outweigh any increases or decreases in GDP, fluctuations in currency markets or what party controls what branch of government. Remember, this is a long game we are all playing and that short or even medium term periods of uncertainty generally don’t have a lot of impact on the likelihood of success or failure. That said, periods of uncertainty do have an impact on short term results, as customers who may be ready to invest with you may find it equally easy to put that decision off for a quarter or two until the dust settles. Thus, I would encourage you to, on the margin, be cautious and conservative with your incremental spending decisions. Further, short term fear and uncertainty can have a real impact on the capital markets, and while we did not see the large drop in the S&P it looked like we might see late Tuesday night, I would guess that the fund raising markets for each of your companies will be more challenging than not in the coming 6-12 months, so if you have an opportunity to raise money now, take it but don’t spend it, and if you need to raise money in that window, think about ways to defer, or at least minimize, that need.

More difficult, and I am treading on more tenuous and potentially emotionally charged ground now – but I will do so as there are certain values we hold strongly as a firm – is what this election says about our society and what we can collectively do as both company leaders and leaders in our community on a go forward basis. A few thoughts come to mind on this front. First, is to remember we live in a fabulous country and our political system has been remarkably resilient over 200+ years and we should respect the democratic process even if we may disagree with the outcome of this particular election. Second, is to take the high road and focus on what we can all do moving forward. If the divisive rhetoric of the campaign, with its anti-immigrant, misogynistic and racist overtones made you sick to your stomach, let’s address that in ways we can control and actively seek to model a culture of inclusivity in our companies and create opportunities for people who were born outside this country, people of color, women, different sexual orientation and generally embrace diversity in all of its forms. It will not only set an example for others in our communities, it will make for stronger companies. Finally, it became clear with the surprising nature of this election that those of us in the tech community living in our coastal bubbles, have potentially lost touch with the impact that the rapid pace of change has had on the American workforce, so I would encourage all of you to think about ways we can improve our communities and our country, not only by building great companies, as entrepreneurs are indeed the engine of economic growth in this country, but also by thinking creatively about whether there are ways to hire team members outside our mainstream cities, or to get involved in educational opportunities for those less fortunate, or to think how our innovative approaches to business can be channeled to address issues with a social objective in addition to a profit objective. And with that, I will get off my soapbox.

Listen Up!

I spent a lot of time over the holidays catching up with my family and friends. It seems forever ago, but as I reflect on how enjoyable as it was, and it was enjoyable, I was struck by how few people in the world would be considered “good” listeners. This led me to reflect on how many of founders I meet who are so busy being in in “pitch mode” when speaking with investors, customers, or potential employees, that they forget to listen actively.

Before relating this back to the start-up world, what are the common habits of bad listeners?  

  • Talking about themselves… excessively. Most people are too busy talking about themselves that they are incapable of taking a genuine interest in someone else. This leads to elongated, agonizing monologues that removes the opportunity for any genuine exchange of ideas.
  • Relating what you say back to their life.  Also known as “one-uppers,” these people immediately interrupt what you’re saying to somehow relate it back to themselves, implying that they have a better or more interesting experience with the subject at hand. While their experiences may indeed be more interesting, as they do this they are constantly thinking ways they could chime in with a personal anecdote rather than actually processing what the other person is saying.
  • Changing the subject. If someone changes the subject while you’re talking, they either have no idea what you’re talking about, or simply have no interest in what you’re saying. In both case scenarios, the person is not listening actively. This also makes the person seem careless, and unable to connect emotionally or cognitively with another human being.
  • Saying “yeah” or “uh-huh” to hurry you along. A nod or yeah can be a helpful social cue to say you are listening, but when over used it is a clear sign that the person is not absorbing any of the information you’re sharing. Along with the other bad listening habits, rushing someone along when they’re speaking hinders their willingness to listen to you when you speak. Bad listeners wait impatiently for their turn to speak, and still expect undivided attention.

With that said, it isn’t easy to be a good listener. Research says we talk at 130 wpm, listen at 400 wpm, and think at 1000 wpm. So even if there is genuine interest in what one is saying, it’s extremely easy for the mind to wander.

Active listening takes effort, patience, and understanding. In this Wall Street Journal article, Graham D. Bodie, a communications professor at LSU, states that “active listening starts with the real desire to help another person think through their feelings. Don’t try to fix the problem right out of the gate, and don’t rush things.”  It all starts with being genuinely curious about what the other person has to say and asking open-ended questions, but having good body language, maintaining eye contact and giving well-timed verbal cues also helps signify that you are engaged in a conversation and gives the speaker encouragement to continue confidently.

So… why is this important in regards to founders?

In so many pitches I receive, the meeting starts with a conversation, but then out come the slides and the founder moves into “pitch mode” and the listening and exchange of ideas stops.  No matter how well honed a pitch it is, this represents a lost opportunity as I believe how founders listen and take in feedback is a meaningful indicator of whether or not their company will succeed. Point 5 in this article is right on.  People who are naturally curious see conversations as learning opportunities.  And founders who are naturally curious are going to be more successful.  Too many founders are not open to criticism and potential change, which could help them shape and sharpen their idea, and many resist open-ended questions and conversations as they feel they won’t like the answers or that they can’t control the conversation.  [As a side note, I also see the reverse where founders take everything a potential investor says as gospel and they agree with everything.  This is even worse.]

Active listening, and the genuine conversation it begets, on the other hand is is not only a sign of respect, but a sign of intellect and it shows you are a learning machine with an ability to accept and consider input and be open-minded, all of which demonstrates strength, not weakness or vulnerability.  Further, particularly for early stage companies in a fund raising setting, a genuine conversation builds relationships and deepens a connection, which is ultimately the basis upon which many investment decisions are made.  The converse also applies.  A potential investor who is not a good listener will be a terrible board member and advisor as they will never have taken the time to truly understand the issues you are facing and even if they do, they will be too busy promoting their world view for their advice to be meaningful.

Outside of the investor setting, good listening skills are even more important when recruiting or speaking with potential customers.  If you take an active interest in a potential employee and listen carefully you will come away with a much better sense for how they think, what is important to them and whether they will culturally fit your company.  With customers, if you immediately go into pitch mode you lose a valuable opportunity to let the customer articulate their issues, priorities, and organizational processes (including how they buy) and miss, as a result, valuable opportunities to shape and modify your approach to best fit their needs.  

If founders took a step back and listened more often, it would benefit them greatly, not only as the founder of a company, but as a person as well.  Listening actively will help all of us build our relationships, our businesses, and our knowledge. It would also make for a more enjoyable holiday break.

Leading high performers

In my #ifiwereafounder tweets, I had a few comments related to hiring high performers and team building, not only for finding a co-founder, but also more generally.  What I did not cover, as the CEO of one of my portfolio companies recently so correctly pointed out, is what it takes to manage and lead a team of high performers.  This post will attempt to shed some light on this topic.

Developing, managing, retaining and leading high performing team members, whether they are right out of school or seasoned executives, is obviously critical to the success of any start-up venture.  But these folks, by the nature of their intelligence, curiosity and drive, can also at times be a handful to manage.  They also know they are great and have plenty of other opportunities, so keeping them engaged, focused and happy is important.

In my experience, and from observing many successful CEOs over the years, the following are critical points to focus on in leading a team of high performers:

  1. Create a sense of ownership and identity by connecting what they are working on with with the broader goals of the organization.  This is critical across the board, but with A players there is a constant need to feel like their ample skills are being applied to issues that move the needle for the company.  Sometime this is obvious (i.e. closing a key account from a sales perspective), but when it is not, make sure you have clearly articulated short and long terms goals and connect the dots for people.
  2. Ensure the goals are expressed in terms of ambition, not just dollars.  As you connect the specific activities and tasks to broader goals, ensure these goals have meaning beyond just numbers.  Yes, growing revenues, hitting budget and creating shareholder value are important, but high performers are motivated by feeling like they are part of something truly important that will create an impact on the world.
  3. Delegate and provide autonomy, but take an active interest in what they are doing.  With a clear linkage between their team's focus and broader goals, strong leaders know that the best approach is to step out of the way and let their high performers execute fairly autonomously. That said, this should not be translated into a perception that you don't care about how they are doing what they are doing as high performers will be proud of the approach they have taken. If you take the time to understand this, they will reward you with further creativity.  
  4. Find the right scope for their activities with a balance between stretching them, but not stretching them so much they feel like they are set up to fail.  In a resource constrained early-stage company this is hard, as there is a tendency to keep putting more and more onto the plate of your high performers.  This is great, but know their limitations, listen carefully to when they feel like they are getting stuck and intervene before this becomes demoralizing.  
  5. Look for opportunities to let them stretch their wings outside of their core domain.  If you have a high performer in a specific domain, seek out opportunities to get them exposure to other parts of the organization.  This helps align their interests with that of the company more broadly, allows them to keep learning and facilitates cross functional cooperation across your team.  Special projects, critical sales situations or thorny customer service issues can often be good situations to involve others in developing creative solutions.
  6. Recognize success and achievement.  This is perhaps obvious, but as one of my CEOs observed, high performers all have a little diva in them.  Acknowledge this diva publicly and privately, but also in a demandingly honestly way as false praise for easy accomplishments is seen through pretty quickly.  
  7. Take pride in their development.  Our best CEOs view their job as grooming the next generation of leaders, and they revel in the success when people step up.  If seeing these unexpected accomplishments and this growth and development does not get you jazzed, it maybe you are not in the right role.
  8. Take an active interest in their life outside of work. Early stage companies can be all consuming and it is easy to lose sight of the fact that your high performers will have a life outside of the office.  Recognize this, know what is important to them and understand if there are extenuating circumstances outside of work that may impact their abilities inside work. 

I am sure I have missed some points, so let me know what works well for you!  I would also like to give a special thanks to several CEOs of Flybridge portfolio companies who provided invaluable advice on this post.  They are the real rock stars, and I would like to publicly acknowledge their inner divas.

On Being Scared Shitless



Of all my #ifiwereafounder tweets, this comment resonated with the most people.  Profanity aside, as that always sells, this is because I acknowledged what every founder feels and almost never publicly admits: the day to day building of a company from scratch is scary.  These fears range from those that are inwardly focused (I am doing things every day I have no experience doing), team focused (how on earth did I become responsible for the livelihood and development of all these people), customer focused (we are at risk of screwing up our largest account), market based (will enough people buy what we are selling or if there are, will our large competitor react quickly enough to crush us ) to financial concerns (we run out of money in 8 weeks and I have no idea where the next slug of cash is coming from).  

The path through these fears is the second part of the tweet: be action-oriented around things you can control.  Don't fret about things outside of your control.  For example from the list above, what you do today has very little to do with whether your large competitor decides to try to crush you.  Every cycle you spend on things you can not impact distracts and bogs you down.  Instead, focus relentlessly on what you can do to keep pushing forward every day.  Break down big scary tasks down into manageable and achievable chunks.  Celebrate small successes and develop a culture of getting shit done.  Figure out quick data driven approaches to research your concerns and react accordingly.  Recognize you don't and can't know everything and reach out for input on your path forward from your team or advisors when you are outside of your comfort zone.  If you are confronted with a WFIO moment, read Scott Weiss's excellent post on leading from the front, getting the best brains around the table and realizing it is never as bad as it seems.  Speed, desire and unique insights are why start-ups win.

In a subsequent tweet I said "I would have one person to share my deepest fears and worries with" and this too is critical.  Generally I am a fan of leaders that are more open with their team than not, but I also recognize you can not share everything broadly.  But internalizing all these fears is also counter-productive and will lead to even more sleepless nights, and there are enough as it is.  So have someone you can be completely honest with as talking through your concerns, issues and worries makes them easier to address and overcome.  Ideally this person is your co-founder, but could also be a key mentor, other CEOs in a group you regularly meet with, your significant other or, heaven forbid, an investor you trust.  If you can find that unique combination of 100% supportive married with honest objectivity you will have found the right mix.

Finally, if the reactions I had to the tweet are any indication, recognize you are not alone.  This in and of itself is helpful.