The Right Time + The Right Team + The Right Technology

Team Time Technology


I have been working with a number of early stage teams going through various stages of fundraising and using this diagram to help explain my thoughts on some of the questions they will come up against.  This is certainly not all inclusive, but it helps me outline the key points that I think must be overcome by an early stage team to convince an outside party to invest their capital in their company.  Many of the questions and comments I have seen happen in pitches fit into this venn diagram.  The best example I have of this is looking at what happened with YouTube; it came about at the right time, with the right team, and the right technology. However one of the only things they could control was the team – assembling the right people to take advantage of market conditions.

The Right Time
Starting a business at the right time is almost completely outside of someones control.  There are multiple macro/micro economic factors that can contribute to success or failure.  However, I say almost as there are indicators that can be used to see if an idea has a shot at working – either something that has failed in the past, or something completely novel whose time has come.  In the case of YouTube there were countless other examples of online video providers, some during the dot com boom, that didn’t quite make it.  Why not?  Well, for starters I don’t believe there was the ubiquity of broadband that existed in 2004-2005.  If you had a video site in years past with a dial-up service there was no video compression system in place yet that would bring quality and convenience that people needed to actually use and browse a site effectively.  There was also no hardware to make small videos at the same pace as the mid 2000’s.  Think about the explosion of digital video recorders (remember Flip cams?) that happened right around the time of YouTube launch.  Using the Flip example (launched in 2006) there was suddenly a very affordable digital video camera that you could instantly connect via USB.  The next logical progression of this video content explosion was a place to put it – enter YouTube.

The questions associated with this circle for me are;

  1. Why is now the time this Company will succeed? (vs. 5 years ago or 5 years from now)
  2. Is the market ready?
  3. Are customers ready?
  4. Are there enough buyers/sellers today?
  5. Is there some special moment happening that makes this the right time to exist?
  6. What external factors could help/kill/affect what your roadmap looks like for the next 6 months?

The Right Team
I believe that the first 10 people at any startup will make or break the Company.  I know this is a strong statement as people change roles all the time, and I need to get my thoughts fully written down on it, but it has been my experience thus far.  The first set of folks usually set the culture and cadence of the entire operation.  If you look at most early stage companies there are usually a few people that make a 10X difference in the early days and end up leading the teams and departments later on.  This is not always the case but when a core founding team departs an organization it is hard to understand how the heart and soul of a company isn’t gone too.  If this happens years later and there are new leaders in place, this can be the right time for them to leave and its actually a good thing for a Company.

Digressing back to my example, YouTube was founded by 3 early PayPal founders that experienced a real existing pain; there was no place to share and view videos online for recent events.  Whether you believe the dinner party story or the news events story (more here) doesn’t matter – the reality is that there was no place to house and share video online and this team was well poised to find the solution.

The questions associated with this circle are things like;

  1. Why this team?
  2. If someone else got $XXM, could they assemble a better team? Do what you are doing faster/slower? why/why not?
  3. What makes this team well positioned to succeed in this market over competitor X, Y, Z?
  4. Who is missing from this lineup?
  5. Who are the next 5 hires you are going to make if this funding comes through?
  6. How are you going to compete for talent against X, Y, Z?
  7. How are you going to retain this group?

The Right Technology
This is a contentious circle for some as some investors rely on the tenacity and vision of the founders over technical abilities.  In my experience being brought up around a thesis of having strong technical co-founders its hard to get away from.  Aside from the abilities of the people, the real question here is around the state of the technology being used and many external factors.  Coming back to my YouTube example there were again strong external factors that were beyond the founders control that made its success possible.  The first is that there was an explosion browser based video players that were found in almost all computers – Adobe Flash.  Say what you will about the players today (they are on the severe decline), around the time of YouTube it was incredible.  With most systems having the player, YouTube was able ride on the coattails of a ubiquitous player that could handle and stream video on most big platforms.  Previously used for interactive and complicated websites, the Flash player for video was perfect.  People could get video buffering in the background with their broadband connection and see basically “live” video without the previous problems of downloading and dealing with codecs and corrupted files.  The technology used here matters as there are tons of carcasses of online video companies from the dot com boom that didn’t survive as they didn’t have the right technology in place.

The questions associated with this circle are things like;

  1. Is this Company using the right technology to solve this problem?
  2. Is the world well equipped for this technology to be brought to market? (Flash/YouTube example)
  3. Do you have in house technical talent, or is the technology somewhere else?
  4. What is the defensibility of this technology?
  5. What breakthroughs are you waiting for? Holding you back? Are you driving?

This is certainly not meant as an all encompassing series of VC questions, but it helps me wrap my head around where a Company is based on their answers.  The center of this venn diagram defines for me that this is something worth taking a look at.

Contact your own customer service system

Things get done when the people who can affect change experience pain. What I mean by that the people that are most able to fix problems are the people in an organization who probably have no idea that it is happening. Therefore I believe every Founder or CEO should contact their customer service centers, as if they were a customer, immediately.

call-us-1049266_640I recognize that a call to have CEOs dial their support lines may not happen by the likes of the Fortune 500, but my hope that one person who reads this will go through their support channels today and make improvements.

Almost all call centers can be improved but the metrics, dashboards, anecdotes and discussions in conference rooms are blocking progress. If a company leader spends time on the first point of contact, or perhaps the point where a customer is most in need, they will find a place to spend cycles that will help their business. There is so much energy spent on all the customer touch points; phone, email, txt, live chats, and more – but it feels most are spread too thin.

You don’t have to look far to find companies with customer services woes. Comcast and Time Warner are notorious for having bad customer service. The first line of defense here is the phone support system. This is a power law in action that is not being fixed. If they spent cycles on the single point of contact people hate the most, would it have halo affects on the rest of the business? My answer is yes.

I have a had my fair share of customer service woes and I am usually pretty good at solving them. So much so that people that know this about me get me involved when they can’t make progress. It’s not always just about “talking to a supervisor” but goes into how you communicate and why.  I believe in the halo affect that a good product or a good customer interaction can have and this feels like an easy way to make customers happy.

So whether its by phone, email, livechat, or other means – contact your customer service team to see what the experience is like.  If its perfect that you can scratch one more thing off your todo list 🙂

Goal setting and tracking

I have read in countless books and blog posts that you can’t change what you don’t measure. This is especially true in fitness and weight loss but also the workplace. Measuring things holds people accountable can backup actions with data to show what worked and what didn’t.  This is true of individuals as well, and why I am trying something new this year.  I am working off the Derek Sivers /Now movement (his Now page) and creating a public way of holding myself accountable and tracking things a little better.

It seems others agree with this method and there is now a growing number of people participating on the site.

I have created my own now site, which is a way of helping me prioritize – Eric Friedman Now

I have also outlined a set of 2016 goals, some public and some private that I am going to hold myself accountable to.  The added pressure this year is that I have shared the private goals with a set of close friends so that I am held accountable as well.

Accountability is important to me with teams and direct reports, and therefore I should hold myself to the same standard.  I have reviewed some of the best ways to track these things and I think putting them out publicly is a good way to do it.  I have also started using the Strides app, and making small tasks that I can check off each day and each week.  This builds momentum as you are less likely to break a chain once it is started.  I once read somewhere it takes a few weeks to start a habit for adults, and not a long time of missing them to fall off.  I hope that putting this out there helps me and I can refer back to see how I did.

So in summary I am doing 4 things to track goals and measure;

  1. Strides for daily/weekly things for habits
  2. Goodreads for books
  3. Public Now page
  4. Private group for 2016 goals

Looking forward to a great 2016 and reporting back to see if this works.

It’s the questions not the answers

Slack recently had an outage, which happens to every company, and people noticed on Twitter – wow what a reaction!

I was reminded a lesson I learned from Brad Burnham while I was at Union Square Ventures; it’s the questions and conversations that are important, not the answers. 

This came about from Brad as my colleague Andrew Parker and I were arguing over whether or not we should be checking in to a place on Foursquare.  We had gotten takeout/delivery (I can’t remember which). Following the “rules” you should check into places that you go (hey, this was before Swarm ok?). However we definitely purchased something from the restaurant, so didn’t that warrant letting them know? There were clear benefits; sharing on Twitter/Facebook, letting the business know, training the Foursquare system. There were also plenty of challenges; the location services may count this check in as “cheating” given we were so far away, we weren’t technically “there” if someone came looking (this happened a lot in the early days).

The list for both sides goes on. I think this is where Brad jumped in and stated that it didn’t really matter who was right or wrong – he was much more interested that the discussion was taking place. He said that many times it’s not about having clear rules for digital games, but rather the constructs make people think, and question – the discussion is the most important.

This brings me back to Slack; watching the reaction of people was fascinating. It didn’t matter if it was an outage, a hack, an AWS problem (I don’t even know if they are on Amazon) but rather that people noticed. Being in the zeitgeist vs having hype are two totally different things. This downtime brought companies to their knees, and people couldn’t work without it. That’s the most important thing to notice. I am sure we will get an explanation and post mortem, but people will still be using Slack. It reminds me also of the Twitter outages of the early days – only now there is a place to complain! (On Twitter – how meta)

As I look at companies both through my operator and investor lens, this discussion is the strongest signal to Slack dominance and usage across organizations and companies.   

Many see the valuation and argue, I see the discussion and see value.

Amazon Dash Buttons

I recently got around to ordering and trying out an Amazon Dash button, and have been thinking a lot about what they mean for customers and homes.

For $4.99 you get a wifi enabled device that uses your Amazon Prime account to reorder items you pre program to get from the brand. In my case I got a Cottonelle button and could choose between a few order sizes. There is no difference between the buttons and I have heard varying accounts of how much brands have paid to have themselves included.

In the future, our homes will certainly be more connected and “smart” than they are today. The question is; what does the bridge to the fully connected home look like? I believe that the Amazon Dash buttons are a stepping stone to wiring up your home with a series of IoT devices and appliances.  What is the difference between having a Tide button stuck to your washer and having a built in button with a GE washer? What if your bathroom mirror had a touchscreen selection of Amazon prime items to reorder? What if your coffee maker had a re-order Amazon button built in?  These questions and more will be answered, but the hyperbole of previous commercials and hype showing futuristic homes never really got us there.  Since nobody appears ready for this future, Amazon is building a novelty approach to something we will look back on as obvious (and most will also be oblivious).

Switching costs and trials for CPG manufacturers are so high that getting into the production of products and buttons makes a ton of sense. Preprogrammed buttons make the technology easy and accessible, but I could imagine a future of programmable buttons to your own liking are possible.

Here is the device with human hand and my dog for scale:


Many laugh today at the buttons, citing that a phone order is easier and faster but I believe that is short sighted. Instrumenting your home with wifi connected devices and beacons is a boon for Amazon and CPGs as this playful approach makes this encroachment all the more powerful. Reorder habits and brand affinity models are set to be influenced by branded buttons and so much data can be gleaned from this consumer usuage. I look at all this as step 1 of 1,000 in the fight to get IoT products and services into homes. Amazon is well positioned in this battle and I am excited to see where it goes.
Setup of my button was easy – a few quick steps and it was soon synched with my phone and confirmed to be ordering a specific product in question.  Obviously there is no difference in the hardware of the buttons to order another product, but things are locked down to Cottonelle for this one.  There are now also many examples cropping up of people hacking the Amazon Dash buttons for their own use; here is a great one tracking baby actions

Once setup I placed it in a pantry shelf (stuck on the wall, but with optional hook).  I believe that this is a path to getting many connected devices into your home, and in areas that do not typically have power going to them.  I certainly can’t imagine shelves of buttons from every brand, but I can see a path to getting something similar.


Having seen the rise of centrally connected devices, like the Amazon Echo, its clear that you can have a multi purpose device that gets things done.  The more beacons and signals that appear in a home from a ecommerce source, the higher the likelihood and affinity to that source will be. The Amazon Echo provides utility and convenience, and when you start to see the ordering capabilities of such a device its a powerful combination.  I can also imagine a future of IFTT type of controls for such buttons and controls.

The future of the connected home probably won’t be an AT&T commercial from the 80’s or the Back To The Future scenes we all know, but it will have themes from each that will seem as familiar as the technology in our homes today.



Tools I use: SizeUp

SizeUp bills itself as “the missing window manager” for Mac and I totally agree.  This nifty utility stays open on your desktop and allows you to quickly throw windows in different places very easily, and maximize them to full screen (without that annoying OSX version of full screen.)

Screenshot 2015-08-31 14.37.25The tool itself costs $12.99 but is well worth it. I use it every day first thing to maximize windows (CTRL+Command+ALT+M).  It even has a handy feature that shows you how much time you have saved since you started using it.  If you are thinking about the cost benefit, after a few weeks of saving time stretching and maximizing windows, it should pay for itself.

This great utility is by the folks at who make a number of great tools/services for OSX.

Packed with tons of options, I think SizeUp is critical for anyone that is trying to use a laptop + monitor combo on a desk, and definitely required for someone that is rocking 2+ monitors at the same time.

Sometimes it is the simple tools that make the biggest difference, but I was amazed to learn that there is no good solution for Mac for this problem.

A full lineup for what is available is below;

Screenshot 2015-08-31 14.33.26

If you are still unconvinced, there is basically a freeware option that lets you use the fully working version with a status box that requires you to click continue.

The yin and yang of the engineering team and the sales team

There is a balance between developers and sales people that allows them to get along. This is sometimes the result of one team pushing the other to its limits, often the sales team pushing the limits of the engineering system already in place.  Its a dance that happens within startups everday.yin and yang

Through planning, brainstorming, innovation, and sales – these groups have  to work together in companies to get things done.

The power of the ignorance on the business/sales team side provides a childlike imagination that creates scenarios nobody has thought of, are not relavent, are overly complicated, and my personal favorite “computationally expensive” on the product.  Engineering can have the same imagination, but it is usually tied to the work necessary to complete the task and operates within the realm of possibility of the app. Vetting the technical feasibility ideas is the job of a strong engineering team keeps things in check.  They are always making room for innovation, growth, scaling, and constant  looking at security concerns.

The balance comes from the “asks” from each group that are constantly in flux.

On the one hand, the business team assumes anything is possible. Although technically this is true, engineering teams think in binary terms and all requests have a cost to other projects and future support.

Product planning is never easy, and prioritization is even harder. When you work on a web/mobile application either of those can change at a moments notice and a team has to be able to pivot in another direction at a thousand miles per hour.

Turn to fast and things get out of control. Turn too slowly, and you miss the mark completely.

I believe both teams need each other to stay in check. The ignorance of the business team to dream big, and the reality of the engineering team to keep things on the ground – and vice versa. It is not always the same balance, but the constant struggle between both groups is what breeds amazing products.

I have learned that these skill sets that can only be learned in a live environment which results in a win for users, customers, and the Internet at large as a result of this never ending storm.

To build a network, first help a network

I was talking to a friend a couple of weeks ago who wanted to break into and meet people within a specific vertical of startup tech companies. His approach was to feign interest in their offering and take a pitch from a salesperson. The thinking being that although there was zero chance of him becoming a customer, he could get time with a rep, learn about the offering and “build a network”.  I told him this wasn’t a good use of his time, and certainly not a good use of their time. The founding premise of the interaction would tarnish the reason for getting together in the first place.networking

I then shared a lesson my mother taught me about friendship which is; “to have friends, you have to first be a friend”. My professional version of this is the title of this blog post; to build a network, you have to help a network. You see it’s less about getting on a persons calendar for coffee or a meeting and more about finding out what you can do to help them.

A lot of people reach out for “informational interviews” or to “pick your brain” on stuff and the value exchange is lopsided from the start.  I hear of many of my friends/colleagues/CEO’s who simply decline by not answering.  This doesn’t help either side as the people writing the emails just figure they have to send more, be more persistent, or add more people to the top of their funnel.  This is a mistake, and instead they should think about the what I call the coffee equation which is putting in more time/energy into the ask before asking for something in return. You should give more first if you ask someone to have coffee so they know the agenda and feel good about spending the time.

Going back to the macro point, many people want to build a strong network.  To do this first by helping others you will not only understand their pain and problems first, but be someone that the person doesn’t mind connecting with in the future – especially after knowing you understand their world view and potentially help solve some of their problems.

To build your network, first help a network.

The State of US Tech Funding

The folks at Andreesen Horowitz and Benedict Evans put together this great presentation on The State of US Tech Funding.  It is embedded below and a lot of it rings true for what I am seeing.


I also agree strongly with Slide 39, that more smaller rounds are happening
Smaller Rounds
With the companies I advise, I have seen more of them raising a higher quantity of rounds at the so called “seed” stage.  The synonyms and nomenclature behind these rounds are also changing.  What was before a seed round is now a friends and family round.  Some even call these activities genesys rounds, or pre-seed deals.  Whatever the language, they are happening more frequently at smaller amounts – to my knowledge.
I also agree that while creating and scaling a software business is getting cheaper, reaching a larger online market is a growing challenge.  There are more SaaS tools and mobile marketing programs to use to “make it easier” but these end up adding to the burn of these Companies.  I jokingly referred to this trend as a re-distribution of funding via expensed $20, $50, and $100+ monthly SaaS plans happening between each company (no, thats not really happening but it is on a very small scale).
Great presentation to dive into to get a nice comparison between now and then, and to form your own opinion.