All That Wander…

I speak to a bunch of founders every week.  They generally begin the conversation full of confidence as they describe their plans and results-producing execution. At the end of the preamble I usually say, “great, guess you don’t need anything from me.”  This is often met with a stare that begs me to ask, “how are you REALLY doing?”  Founders get caught in the always-be-pitching fallacy.  The one which states that anyone could be a potential investor, customer or partner.  But pitching people that are there to help; advisors, board members, or peers minimizes the value they can add.

Founders need to remember that despite what they see coming from a conference stage or tech publication they are not alone when it comes to “not knowing.” And all of us need to ensure that founders know that being in that place is OK.

I have been doing some research on polymaths for a client.  These are the folks that flit from domain to domain or try out crazy ideas only to fail or think that learning to play an instrument is a business investment.  They are the wanderers. Jeff Bezos in the AMZN 2018 Annual Report puts it this way.

“Sometimes (often actually) in business, you do know where you’re going, and when you do, you can be efficient. Put in place a plan and execute. In contrast, wandering in business is not efficient … but it’s also not random. It’s guided – by hunch, gut, intuition, curiosity, and powered by a deep conviction that the prize for customers is big enough that it’s worth being a little messy and tangential to find our way there. Wandering is an essential counter-balance to efficiency. You need to employ both. The outsized discoveries – the “non-linear” ones – are highly likely to require wandering.”

Read the first 8 pages of the report to get a full dose of Bezos, including his inclusion of the 1997 letter to shareholders, which he includes in all annual reports.  And while thoughts of being a fraud, being lost, and fear swirl around your head this weekend putting you at the bottom of the founders’ well, look around, and know you are not alone.  And say hi to Jeff while you are there too.

The Next Frontier for Startup Optimization?

Last week I had the opportunity for a long overdue catch up with Kate Yoo McCrery, Director at Loyola university New Orleans. My conversations with Kate covered a wide range of topics from the recently released report on the New Orleans startup ecosystem  to how an English degree can teach you systems thinking (she makes a solid case). One topic that we discussed is one that has been rattling around in my head for a while, what’s next for the startup toolkit.  With concepts like lean, agile and the business model canvas becoming almost a 101 curriculum what concepts, tools, or methodologies are on emerging for high performing startups?

My answer to this question comes from a personal bias created from experience as well as an observance of the trends and discussions in startup land.  I believe the next area of focus for startups, and specifically founders, is inward.  While the prior years have focused externally on product, market, customer, competition, business model and value proposition, I think the upcoming years will be defined by founder focused “inner-preneurship”. Better founders build better businesses.

When Hank Torbert and I co-led our cohort at Idea Village there was one thing we were clear on. The quality and ultimate success of a company was not our primary goal, most were led by first time founders who statistically don’t hit home runs. Rather success for us was defined by improved founders.  Founders who were better prepared to launch and grow ventures.  This was consistent with investors’ priorities of banking on the founding team more than the business in its nascent stage.

The broader startup universe seems to be moving this way as well.  Several years ago there was much discussion about “imposter syndrome.”  Combined with the suicides of a couple high profile founders, metal health started its climb to the forefront.  Recent years have also featured the growing awareness of “bro-culture” and most recently the fall from grace of once-unicorn darling WeWork.  These examples bring into focus the potential limiting power of the founder.

During this same time period we have also witnessed the ascendancy of meditation apps and the increased use of coaches for founders. Once viewed as powerful forces of disruption, founders and the culture they either consciously or unconsciously foster are increasingly seen as an asset to be optimized. Authors such as Jason Fried, Ryan Holiday, and Jerry Colonna are finding huge audiences for their messages of a sane workplace, stoic principles and self inquiry.

My personal bias for inner-preneurship stems from my own battles with anxiety and depression.  For the last couple of years, despite releasing a open sourced book, advising a number of amazing startups and completing some exciting client work for leading companies, I felt empty. Crippling anxiety attacks and bouts of depression that left me bed ridden culminated this past summer in a clear signal that my problem was not “out there”, but rather “in here.”  My inner work, supported by the authors cited above and others, has allowed me to find my joy again and reconfirmed, with a new confidence, my work.

In retrospect I believe that many of the founders I have worked with could and can benefit from inner work of their own. What Colonna terms “radical self-inquiry” has led me to improved communications, stronger relationships and improved clarity of vision. I am a better advisor, consultant, collaborator, boss and friend. I encourage all founders and leaders to explore the value driver that is them.  No longer viewed as a weakness, developing one’s inner capital may be the best investment in your company you can make.



The Final Piece of the Puzzle?


The announcement this morning of Louisiana startup Waitr’s acquisition was a welcome addition the startup story long  emerging here on the Gulf Coast. Exit’s are a key piece of of a startup ecosystem for two reasons.  First they raise the profile of the ecosystem, making it a legitimate hub for investors and other startups.  The second is that it creates smart angels. In the beginning of a startup ecosystem’s life it often has to rely on investment dollars from individuals that have made their money from corporate careers or inheritance. No disrespect meant, those checks still cash the same.  But when the angels have made their bankroll in the entrepreneurial trenches things change.

Deals get done faster as newly minted angels understand the pace that startups have to work at.  The unknowns associated with a startup’s journey are most easily grasped and weighted as former founders have been through it before. Finally, post funding, these new angels add more than just cash to the startup.  You only need to Chicago’s ecosystem, long active, pre and post Groupon when a whole new group of investors sat across the tables with founders with the knowledge of having sat in their seat prior.

While the $308 million dollar price tag doesn’t make Waitr a unicorn the article states that $50 million of the proceeds will be paid out in cash. Let’s hope some of the equity holders put their hard won experience and cash to work.


You can read the Silicon Bayou article here.

What’s Next


For the last two years I have been leading the great team at VL Group.  It has been both a challenge and a joy.  I have written before about how mentors’ and advisors’ value comes from doing not just coaching. And the last 17 years have seen me frequently going back into doing roles.  I like to think this has made me a more valuable advisor, but it is also fueled by my own desire to actually build stuff.

Over the past 24 months, the VL team has added clients, strengthened and grown existing client relationships, released new products, pivoted the company to a pure SaaS model, and dramatically reduced the company’s burn rate. I am confident that VL Group will continue to innovate in a world of ever increasing streaming. But it is time for me to move on.

One of the reasons I have been blogging for much of the past decade is that blogging, for me, is a way of locking in learnings (you can see my thoughts here). Also, as I discovered this summer, it is about helping you remember what you may have forgotten.  As I was looking at past posts I came across two I wrote 7 years ago, Put Your iPod on Shuffle and Pattern Recognition, that got me thinking about what was next. They both capture my thoughts on cross-pollination of ideas and patterns from one domain to another.

While I have been an entrepreneur my entire life, prior to joining a VC as head of strategy during dot com 1.0 I was what I would now call a product manager for a company called The Forum Corporation.  My time there was almost entirely spent building, and executing an assessment process which looked at the efficiency and effectiveness of learning and development departments (called training back then) in large corporations.  In this role I had the pleasure of seeing the operations for upskilling employees in organizations like Oracle, Microsoft and Goldman Sachs.

For the last several years, on and off, I have been talking with the author of Running Training Like a Business, the book that was the foundation for the assessment capability I headed up, about how startup techniques could add significant value to the organizations in charge of upskilling our workforce. I even wrote a few posts about it on a site I called Learning Hacks. The cross-pollination of ideas like, lean, product management, and agile could be powerful drivers of value for organizations at a time when people and the skills they need are rapidly changing.

“I am taking my skills to L&D”

Ash Muraya and Jason Cohen talk about how startups need to seek out their “unfair advantage.” Something that cannot easily be bought or copied. I applied this to myself and decided that my experience in two domains, early stage companies and learning & development, was my unfair advantage. I can think of only a few people, one of which is my former boss at Forum Diane Hessan, that have the depth of experience that I now hold in both domains. I also believe strongly in learning as a powerful weapon against the inequalities in today’s world and as any entrepreneur knows, without passion you won’t succeed.

So I am off to start a discussion, share ideas and write a book about how the techniques of startups can create unmistakable value in the organizations that drive learning in large companies. Ed Trolley, the author of Running Training Like a Business, and I have already started sharing ideas on our new RTLABv2 blog.  I will also be sharing my thoughts on my personal blog where you can read more about my personal manifesto and mission in this new adventure.

I will continue to write here about startup related issues and ideas.  I will also continue to advise and work with startups.  I know that in a world moving as fast as we are, maintaining my unfair advantage will require continued involvement in this domain. Plus, it is my way of making sure I don’t forget shit.

The Need For Speed

Today’s business world is moving faster than ever. With companies changing strategies, modifying business models and releasing new products designed to improve customer value at a rapid pace, the speed with which startups must operate is increasingly challenged. Execution, not ideas, are the competitive advantage for early-stage companies.

I think startups need look at three dimensions of speed. First, there is speed to product. This is the amount of time it takes from the identification of need to the release of a solution. Second, there is speed to user. How quickly can your product reach the audience that needs it. Third, there is speed to value. This represents how quickly a user receives value from the product. In order to keep pace startups must focus on and continually improve on all three.

The two main components of “speed to product” are needs identification and product development. While agile development has made great strides in addressing the latter, the former, needs identification, is too frequently the result of an inbound request. Startups must use its key business metrics to be drivers of new needs. This information, often known much earlier than a request can keep a startup ahead of the curve.

Startups also need to drive to increase “speed to user”. How can they get more people to experience the product?  Key areas for focus here are your customer acquisition funnel.  How are your channels to market working?  How are your messaging and activities driving conversion through that funnel? Getting users to recognize and “buy” the solution quickly is critical.

The last dimension of speed is “speed to value”. While this dimension is greatly impacted by the other two, by keeping it front of mind, it can also help to inform both product and user positioning. Startups frequently focus on onboarding. In the startup world this means getting a user up and running.  But running isn’t enough the time from running to value is critical. Why is this critical? The average app, for example, loses 77% of its active users within the first 3 days post install. This attrition can be mitigated by delivering value quickly to users. Perhaps not the full value of the solution but enough.  We are and instant gratification society.  What is your startup doing to get its users hooked?

What are you doing to drive speed in your organization?

The Bro Problem


This Sunday’s New York Times contained an article by Claire Cain Miller about the “Tech’s Myth of the Nerd”  discussing the Google memo’s assertions amongst other false assumptions floating around the tech startup community. The ideas surrounding the power of diversity, how to best advocate for it, the pros and cons of gender specific awards (ie. best female founder) and culture have been a topic of discussion amongst my friends for years.  These same topics are now front of mind for many more with all the recent news coming out of SV.

After reminding us that computer programming was originally considered a woman’s job (Eniac, NASA), one of the points made by Miller is that programming for some becomes a way to express masculinity.  That many males who aren’t playing sports or doing physical labor come to see programming prowess as the field of battle. Perhaps this point stuck out to me because of my own youth.  I was reminded of that kid last night, as the world stopped to watch Game of Thrones and I recalled how much taunting I had received for rolling polyhedral dice and imagining worlds of dragons and warriors. No girls allowed.

I don’t code, although I hear my COBOL skills are in demand again. I like to think that the teams I have been part of have been inclusive.  Regardless, awareness of self is a powerful elixir and I try to get my dose on a regular basis.

UPDATE: Rob Usdin (@robusdin) called me out on twitter for using the graphic I chose for this topic.  The graphic is simply a reflection of my own personal experience, cited above, and in no way is meant to lump all RPGers into the “bro” problem.  Apologies to anyone who was offended.


I asked Rick Harris and Gloria Bell to give me their thoughts on bro-culture.

Q: With all the current talk about Bro-culture and diversity in Silicon Valley what role can women play in improving the culture for the women that will come behind them?

Gloria Bell: The best advice I can give women in this industry is – Be brave. Be strong. Know your own limits and be willing to stand up for them. Be open and honest. Speak up.

When women share their stories and stand their ground, action happens. It is hard, but it is necessary. Bonus, you will be amazed at the army of women (and men) who will surround you and support you when you do.

Don’t play into the “us vs them” mentality of men and women in tech. There are many more amazing, thoughtful men in this industry than there are “bros”. Find them and encourage their attempts at being our allies.  There are even more men who want to help but don’t know how to. Or worse yet, feel that their efforts are not wanted or appreciated just because they happen to male. Listen to them, engage them, show and tell them how they can help. Men still out number women in this industry (at least for now!), we need to use that to our advantage whenever possible.

Women need to stop waiting or expecting to be asked and they need to start asking and demanding – equal pay, respect, better positions, board seats, opportunities, etc… Even with our conference we occasionally receive feedback about not having asked someone to speak or a perceived lack of diversity in our speakers. We work very hard to identify speakers and to promote diversity, but we need more women to help us by raising their hands and submitting to our, and other conference, calls for speaking proposals. Don’t buy into the “if I just work hard and keep my head down, I’ll be recognized” mentality. That is not how it works. Work hard yes, but also work to be recognized. Own the responsibility for that. And be willing to make a change if a particular environment is not working for you. There are more tech jobs than there are technologists so take a stand for your worth.

The changes and the ripple effects these actions will make are some of the biggest contributions the current crop of women in tech can make for future generations.

Q: With all the current talk about the “bro-culture” in Silicon Valley, what role does leadership play?

Rick Harris: Any time something bad happens inside an organization, you can usually trace the cause back to the leadership. I’m sure that holds true for the emergence of the bro culture. However, in my experience most co-founders do not set out to create a culture where some people are bullied by others or where people with more power feel they have the right to extract sexual favors from people with lesser power.

Q: So what can you do about it?

Rick Harris:

  1. Look in the mirror. Some CEOs (and partners in venture firms) actually are misusing their power. Are you?
  2. Unintended consequences. Let’s say that you and a co-founder are male. You already know who your next five hires will be. You’re just waiting for funding. Are they also male? If so, you’re sowing the seeds of a bro culture. That is, you develop a bro culture when you only have bros…even if you don’t want to.
  3. Reward systems. Do your reward systems set up internal competition that can get pretty fierce? Bros like to compete. Is it turning ugly? What are you doing to reward teamwork?
  4. What do your values say and are you living them?
  5. Keep in mind that a bro culture with its emphasis on win/lose arguments is not a team culture. A bro culture directs energy toward achieving power internally and in the process losing the focus on customers and product/market fit…where the real winning needs to take place.

If you sense a bro culture starting to emerge, be aware that tolerance for bro behavior is waning in the business environment. Negative press could result in lost customers and investors before you have a chance to defend yourself (or apologize). And then there are the courts. Reputation is hard to rebuild, but a lawsuit could drive you right out of business.

And, one more thing: Just as a founding team of two technical co-founders does not reflect the discipline diversity that will be needed to become a growth company, a bro culture is too narrow a culture to help your company thrive in the complex marketplace where you will need to compete.

In 2017 we have seen several examples of the toxic effects of a bro culture. Think Uber. Knowing what we know from recent experience, it would be beyond too bad for bro cultures to continue to emerge. It would be fiscally irresponsible. Perhaps criminal.

Women In Tech

I first met Gloria while working in the East Coast startup community. We were both mentors for a Lean Startup Machine weekend. I was immediately struck by her positivity and her action-oriented approach (which left my strategic mind in the dust). Her work that weekend helping ideas get validated by social media channels and IRL interviews taught me a thing or two.

Since that time we have both left the East Coast. She, moving from Philadelphia to Texas and me, Delaware to New Orleans.  Watching her work founding and growing the Women in Tech Summit has been inspiring. After far too long we recently reconnected face-to-face in New Orleans.  Our discussion was wide-ranging but expectedly ended up focused on the current issues challenges facing women in technology. As follow-up, I sent her some questions. I think you will find her answers insightful and authentic.

Who is Gloria?

Gloria Bell brings 35+ years of experience, to her roles as Co-Founder and Operations Director of The Women In Tech Summit and as the Marketing Advisor for TechGirlz. In addition to these roles, Gloria provides social media consulting services and is an Adjunct Professor at Drexel University. Gloria has also shared her experience and expertise as a volunteer organizer of PodCamp Philly, PodCamp East and Content Camp, as the former Events Director for Philly Startup Leaders, and as a mentor for Lean Startup Machine and Startup Weekend.

Q1. The current level of diversity in the technology community is a fairly Downstream metric and is a reflection of lack of diversity in technology training years earlier. The current efforts to attract and retain more than just white males in STEM related fields should lead to greater diversification in years to come. Where should we be focusing our efforts in order to deliver results in the short-term as we wait for the Upstream efforts to pay off?

There is no one answer to resolving the lack of diversity in tech. Equalizing gender and ethnicity in tech requires a multi pronged approach – building the traditional pipeline, current recruitment and retention. Many people look at building the pipeline as only a long-term solution and they are primarily correct. It can also be a short-term solution if hiring managers and diversity/inclusion specialists begin to look beyond the stereo-typical “perfect candidate”. Technologists who may have pursued degrees other than computer science or who have received their training through dev bootcamps or internships or self-education can be beneficial members of a team and often be outside of the stereo-typical, young, white, male generally seen in tech.  This melding of the more traditional long-term pipeline with less traditional short-term pipeline is one solution.

Companies also need to be looking at the issues of culture, pay and inclusion when they consider recruitment and, as important, if not more so, retention, especially when it comes to women. Many qualified, experienced women are leaving the tech industry to take positions in other industries or on other career paths. There must be dedicated efforts to retain women in tech because these women are not only the role models for the women in the Upstream efforts, but they are also the women who will attract additional women to a company. In general, women, and minorities, will not bring another woman or minority into a company where they feel uncomfortable, unwelcome, not a fit for the culture, harassed or that they are not on equal pay footing.  If we are not working as hard at retaining women and minorities, as we are at developing a pipeline, the pipeline will not be filling projected empty positions, but will only be refilling current positions.

Q2. The diversity issue in the Tech Community has existed for a long time why do you think it is finally receiving the attention it deserves?

I think the primary reason is that there are finally women willing to speak up. Each woman or minority who speaks up about the issue gives permission for others to do so. With each voice that is raised, the issue gets more attention and more action is demanded. While tech likes to think it lives in a bubble and are the leaders of everything that happens in the world, the reality is that sociological, political and economic factors outside the tech “bubble” are bringing pressure to bear on diversity and inclusion within the industry. In addition, the stark reality of the number of current and future positions that cannot be filled with trained technologists is making people realize that they have to be more inclusive or they will never fill critical positions. Failure to fill those positions could spell economic disaster for some companies.  Diversity and inclusion is no longer just a social imperative. It is an economic one.

Q3. Diversity is often pitched as the right thing to do but there are also solid business reasons for an inclusive team. Why don’t we hear more about that?

Great unintentional segue from my last answer! Because emotional or social imperative messaging is often easier than getting people to pay attention to business statistics. The few published studies get lost in the large number of stories of harassment, pay gaps and bias. We need to be talking more about the business reasons for inclusive teams. It has been repeatedly proven that diverse and inclusive teams produce better products and services. Companies would do well to pay attention to that research and take action accordingly.

Q4. The Women in Tech Summit you founded takes a different approach from the standard conference full of “talk at you” presentations. Why did you feel it was important to offer a something different for the summit?

Action does not happen when someone just “talks at you”. Action evolves from conversations and connections. When we founded the Women in Tech Summit, we had two overarching objectives:

  1. Provide a place where women working on both the technical and the business sides of technology and at all levels in their careers could come together and build stronger and broader networks as they inspired and educated one another,
  2. Demonstrate, through our programming, that working in tech is more than writing code.

It was important to us that we provide an environment and programming that fosters positive action – whether it was someone learning a new skill, hearing about a trend in technology, making a connection to help them find a new job or building relationships with more like-minded women.  We work diligently to ensure that attendees walk away from our conferences with positive, actionable items they can implement to further their careers and that inspire them to stay in tech and bring more women into tech.

Q5. One cause cited for the lack of diversity is unconscious bias. What can Founders do to become more conscious?

Be more conscious. It seems like a simplified answer, but it really is the only true answer. Making a concerted effort to be more conscious and to implement programs and processes that help recognize and eliminate bias is imperative. It is also a necessity that founders create a culture that does not allow bias, harassment, intimidation or other negative traits to exist within a company. They have to be explicitly clear that those things are not acceptable. They have to create a comfortable space where people can speak up when it does occur and that is quickly addressed.

Founders also have to be willing to be open and transparent about their efforts and, especially, about their mistakes dealing with this issue.  One of the most forward-thinking and successful founders I know is Wil Reynolds of Seer Interactive. He has created an amazing company culture. Everyone who knows him will tell you that Wil is one of the most fair and self-aware leaders they know. Yet, even he makes mistakes. He was brutally open and honest in a recent post about his own struggles with bias. This is how more Founders need to be. The more openness and transparency and communication they have with each other and the industry as a whole, the more we will move toward true diversity and inclusion.


Q6. If people want to get in touch with you or learn more about the Women in Tech Summit, how can they do that?

People can learn more about the Women in Tech Summit through our website and by signing up for our email list (the link is on the website home page).  They can also follow us on Twitter – @WomenTechSummit  on Facebook – The Women in Tech Summit  and on Instagram – WomeninTechSummit or they can email me at

Speaking of TechGirlz, I would also encourage everyone to take a look at  All of the post expense proceeds from the Women in Tech Summit support TechGirlz ongoing mission to provide free programming that inspires girls to explore the possibilities of technology.



The 4 Legged Co-Founder


Last November a dog adopted me. This is not some cute word play but rather an accurate description how Charlie came into my life. I have told our “founding story” many times so suffice it to say that a dog, abandoned to the streets of New Orleans, rescued me. Charlie is not my first dog.  There was a family dog for a short time when I was very young and for several years early in my career, I shared the companionship of a Beagle named Cassady.

Because of Cassady, what Charlie has taught me over the last 9 months is more remembering than new, but no less valuable. I have worked for myself for over 15 years. During that time I have had numerous ups, downs and way downs. Such is the life of an entrepreneur.  What Charlie has reminded me is that entrepreneurs can really benefit from a four-legged co-founder. Charlie is mine.

While I play many roles for a variety of startups, my primary one for the last 2 years has been acting CEO for a music technology company. Going from coach back to player is something I have periodically done throughout my career. I frequently say that a lot of an advisor’s “been there/done that” value, in the fast moving world of startups, has the shelf life of milk. Occasionally returning to the role of doer is something that I believe has made me more valuable to the startups and investors that I work with. Doing versus coaching also reminds me of the challenges, both personal and professional, facing founders. Stress, depression, feeling alone and an unhealthy lifestyle are all too common among founders. Having a four-legged co-founder has personally helped me to better handle these challenges.

“It does good also to take walks out of doors, that our spirits may be raised and refreshed by the open air and fresh breeze.”


My day typically starts early and can occasionally run very late. There have been times that I have found myself sitting down at the computer with my cup of coffee in the morning only to rise again after lunch. There has been plenty written about how sitting is the new smoking. That makes my chair habits the equivalent of chain-smoking. I do however walk a great deal. Whether it is to meetings around the city or from my home into the co-working space a few days a week. But on those days with no meetings? Not so good. Now, regardless of the day, Charlie will have none of my sedentary ways. With Charlie by my side, my day begins with a walk through the park and I end each night with a long walk through my neighborhood.  Combined with several walks during the day, sometimes at Charlie’s request and sometimes triggered by frustrating conference calls, my step goal is always met.

In addition to being my fitness coach, Charlie also frequently functions has my emotional support animal. She is more than happy to play an endless game of catch while I try to work out some problem in my head by mindlessly throwing a ball. She also has the intuition to lay on my feet or with her head in my lap when she knows I’m struggling. Her empathy is a great mirror for showing me the mood I am in. The list of emotional benefits provided by pets is long and animals have been used to treat individuals with all types of challenges. “Founder” may not be a clinical diagnosis but it is shorthand for a big bundle of challenges from depression to imposter syndrome. There is a good reason the top co-working space here in New Orleans is dog friendly.

Being a founder is a hard but I believe that there is a four-legged hack that can help. Are you a founder with a dog? How has it helped you? Charlie and I would love to hear about it.

People Powered Startups

I’ve known Rick for 2 decades. It was his research, when we were at The Forum Corporation, that showed me the power that people have to impact a company’s performance.  When we spoke recently, it was no surprise to find out that he had brought this knowledge into his angel investing approach. Following our conversation, I sent Rick a few follow-up questions. I thought you would be interested in his responses. I am interested in your thoughts.

Who is Rick?

For more than 25 years Rick Harris has been a consultant to business leaders and their teams, helping them create more strategic focus and better results. His clients have ranged from executives in the Fortune 50 to early stage start ups. But they all have shared one thing: as their teamwork improved, their performance improved.

Rick is currently an angel investor with Launchpad Venture Group in Boston helping portfolio companies to use teamwork as a strategic weapon. Launchpad consistently ranks as one of the top five angel groups in the country by the Angel Resource Institute’s annual HALO poll of deals done and dollars invested. He is currently working on a project to help better match the needs of portfolio company CEOs with the human capital that angel investors bring to the table. The ideas expressed in this post are his own.

Q1. As an angel investor, part of your focus in diligence is not just looking at the team’s credentials but looking at the team dynamics.  Why is this important to you as an investor?

Credentials are the price of entry. You want to be able to invest in people with the strongest track records. After you’ve established that you have people worth investing in, the question becomes can they work together? If the company has some history, the question is, “Are they working well together?” You want enough difference of perspective in the team that conflict can surface, but not so much that drama takes the place of real work. I look for three things to give me a clue about their dynamics:

  1. Are they aligned around a common direction?
  2. Are the roles clear?
  3. Who talks most/least and does it affect decisions?

By listening to answers to the first two questions and watching the behavior of the team in group discussions, I have a pretty good sense of whether the proceeds of a funding round will go to the purposes outlined in the investor deck, or whether the proceeds will be gobbled up by a muddled team.

Recently I was in a scouting meeting with two co-founders. After several minutes of discussion, one of my colleagues said, “So which one of you is the CEO?” They both said, “I am.” My rule of thumb is that you don’t want to invest unless you feel really good about the answers to these three questions

Q2. What do you look for that indicates a positive team dynamic?

In a seed stage round you’re typically looking at the dynamics between co-founders. And the first thing I look for here is discipline diversity. Ideally co-founders should come from different disciplines—a technical person paired with a marketing person, for example. If that’s the case then I’ll ask one person to tell me why they need the other person’s knowledge at this stage of the company’s development. If they can’t give me a coherent answer, red flag. What I’m looking for is the ability of each founder to talk knowledgeably about the other’s contribution, not necessarily to have the same depth of knowledge. Occasionally co-founders are both technical. If this is the case, I’m reluctant to invest because they haven’t proven they can create a positive team dynamic with other disciplines—something that will be needed to support the company’s growth.

 For an A round the team dynamic tends to get more complex because there are not just co-founders involved. I’m still looking for appreciation of other disciplines. In addition, I’ll also have a chance to see the team in action at an investor presentation. My preference is for the CEO to make the pitch and hand off questions to the right team members. That gives some insight into the extent to which the CEO will leverage her team on other issues and it gives the team member a chance to show their stuff. Series A diligence will also include interviews with individual team members where I ask them to describe how other team members’ efforts contribute to theirs. I’m looking for an indication of interdependence.

Another thing I’ll ask about is conflict: what is an example of a conflict that was handled well and one that wasn’t. I’m looking for insight into how they manage their differences. If they have trouble answering this question, I’m suspicious that people are avoiding conflict. Maybe somebody told them that they should be a “team player”. Good team players hold each other accountable. I don’t want them making nice to each other if they are not in sync with key decisions. That’s how you burn capital without getting anything done.

Q3. What suggestions do you have for founders that are looking to create a positive dynamic?

  1. Step back from the day to day and ask yourself “Why is what we’re doing important?” People love to work for a winning team, but in a start up the wins can be a long time coming and the work required to get there can wear on people. It helps to remind them that what they are working on is part of something bigger than the next line of code or the next market test.
  2. When talking about the importance of what you’re building, be sure that you’re saying something that is truly inspiring to you. Genuine feeling is way more important than rhetoric. If your team can get inspired then the chances are good that your customers will be inspired…and that’s the real goal.
  3. Create a set of values that have meaning for people. Start with the question: “How do we want to treat each other as we work together each day?” Then branch out to asking the same question about customers, and perhaps other stakeholders. You can start with the co-founders or open a discussion with the entire team.
  4. Acknowledge people publicly when they act on the values.
  5. Ask for feedback on how you can do your job better. People love to give advice. Let them feel part of the team by giving the founders some helpful suggestions.
  6. When going through a rough patch (they happen), increase your contact with the team. People can disengage during hard times. The team will perform better if they don’t.

Follow up note: With all the controversy swirling recently over the toxic effects of a bro-culture, I’ve asked Rick to weigh in with his perspective on the role leaders play in feeding such a culture and what they can do to keep their company focused where it ought to be…on customers and growth. Look for his response in an upcoming post.


Adding More Fuel to the Fire

I am fortunate to be able to have coffees, happy hours, phone calls and walks with some really smart people. Having spent the last 15+ years working in and around the startup world my network contains investors, founders and supporters of all kinds. I started this blog as a way for me to capture the learnings I have had so that others may benefit from it (and I don’t forget them). As I move forward with this blog I also want to give readers the opportunity to hear it right from the mouths of the smart people who teach me.

So, in the coming months I will be posting a variety voices in addition to mine. the format is simple, a small handful of questions to provide my friends, colleagues, mentors and others the opportunity to share directly with you.  Sorry you will have to provide your own coffee.Bonfire night fire

Don’t worry there will be continue to be plenty of my own crazy ramblings Half Baked ideas and posts of me just thinking out loud. the goal of adding these additional voices is to make sure that they’re smart messages don’t get lost in translation. I thank in advance all of the people in my network that have and will be contributing. I’m grateful for all that I’ve learned from you and hopefully I’ve been able to give a little bit in return.