Tuesday, December 23, 2014

The Pitchdeck Interview #39

The Pitchdeck Interview #39

Really enjoyed my interview for The Pitch Deck podcast with Gavin McCulley - now out on iTunes. Makes me Episode 39 of a series Gavin is doing for entrepreneurs where he talks with angel and VC investors as well as entrepreneurs themselves. 

You can listen to the interview HERE.

Gavin talks about The Pitchdeck in the video below. Subscribe on iTunes!

Happy Holidays and all he best for 2015!



Sunday, December 7, 2014

JFDI - Julia Shapiro and Jules Miller of Hire an Esquire

Six Habits of Highly Successful Founders


#6. JFDI - Julia Shapiro and Jules Miller of Hire an Esquire


One of the core values that the Hire and Esquire (HaE) co-founders Julia Shapiro (CEO) and Jules Miller (COO) have instilled at their company Hire and Esquire is proactivity. That is easy to say … but what does it mean in startup practice? 

At HaE it means “JFDI” (Just f-ing do it!”). In daily routine when you or I (definitely I) might say "we should schedule a meeting for x" or "we should email y" Julia and Jules pause and just do it at that very moment. So a procrastination embargo.

A specific example of how this works beyond the day to day of office life came about when they talked "legal tech collaboration" with another legal tech entrepreneur at a happy hour. In that dialog they and came up with the idea of a legal tech demo day to bring customers to HaE. What next? JFDI! So over the next few weeks they planned it and made it happen starting with EvolveLaw Demo Day at WeWork with 25 people. Next iteration working with Stanford CodeX to host an event with 150+ people. 

Julia and Jules believe that they have successfully instilled the JFDI approach in (most - it’s a never ending education process) of their team. And they are delighted to see how much team members get done when the co-founders aren’t bottlenecks! But for JFDI to work a) they have to trust your team and crucially b) they need to make sure that their team members have a clear sense of the company’s priorities to frame their independent decisions.

Lesson: JFDI - it’s as simple as that!

For a full list of the Six Habits - click HERE

Win the game of “whack a mole” - Kelsey Recht of Venuebook

Six Habits of Highly Successful Founders

#5. Win the game of “whack a mole” - Kelsey Recht of Venuebook


A startup up is a highly iterative journey. First working to product market fit then moving forwards to optimize your product/service and delivery to customers - so testing and learning to identify what works and does not work. Then you quickly fix things that are not working. 


As you scale you always encounter new obstacles. Kelsey Recht CEO of Venuebook noted that one of her board members calls it "whack a mole". ie you fix one bottleneck and another one is created someplace else. 

What I know Kelsey does very well is having an open dialogue where team members feel they can bring up growth pain points and then address them very quickly. Kelsey’s motto is “don't tell me who caused the problem, just tell me how to fix it.”  

Besides being a smart way to iterate, embedded in this approach is a strong message about the culture of the firm she is building - problems/issues happen all the time so surface them don’t hide them. The whole team benefits when things are more transparent and the focus is on solutions and ceaselessly improving the product and customer experience.

Lesson: There is always a new mole. Whacking it and moving on is a team sport.

For a full list of the Six Habits - click HERE

Build to scale, before you scale – Lisa Xu of NopSec

Six Habits of Highly Successful Founders


#4. Build to scale, before you scale – Lisa Xu of NopSec

I was fortunate to spend the first half of this year as interim CFO at NopSec working with co-founders Lisa Xu (CEO) and Michelangelo Sidagni (CTO) and saw first hand the value of building “repeatable processes” across a startup BEFORE they are needed … so that scaling the business in response to customer demand is much less painful. 

Lisa is a master at doing that … with huge benefits to the organization. We all know that cloud based services have made it cheaper and easier than ever to build scalable tech platforms – or at least an initial MVP version. Having used that to validate product-market fit doing the actual scaling of the businesses involves so much more than buying more compute or storage however. It involves developing and scaling many interlocking processes from customer acquisition, on-boarding, customer service, finances, HR etc. 

However for many startups the challenges of scaling across these other dimensions often are faced when, to use an old tech analogy, the rivets start popping out. This is because the processes that enable that broader scaling often feel like bureaucracy for a start up and hence are deemed toxic … until things derail. For example a key employee leaves and folks realize exactly what she/he did and how are not documented or processes that worked for single units just don’t work at 100s never mind 1000s. 

As Lisa demonstrates, proactively building processes to scale, before you scale, is a smart move.

Lesson: Don’t just be hands on, be hands ahead

For a full list of the Six Habits - click HERE

Pitch, pitch and pitch again – Erika Trautman of Rapt Media

Six Habits of Highly Successful Founders



#3. Pitch, pitch and pitch again – Erika Trautman of Rapt Media

Like many (most!?) start up CEOs Erika Trautman at Rapt Media has spent considerably more time than she ever thought likely or even possible talking to money. In the last three years, which have seen her go from multiple notes to and A and most recently a B round she estimates that fund raising has taken up 40% of her Rapt Media life. 

The statistics about the imbalance in funding of women led companies by angels and even more so VCs are well known and the issues of unconscious (mostly) bias that lie behind this are complex and subtle. However as Erika wrote in an article for Entrepreneur Magazine, after talking with 200 investors she learnt a lot. 

Obviously appreciating quickly, if not from the get go, that fundraising is a key part of the CEOs job description is one. But more so developing you story told by an authentic you and seeking the investors with whom that story will resonate. As she put it: “ultimately, shrewd tenacity may be even more important than selling the dream.”

Lesson: Pitching is a core function of the CEO - but only pitch as the real you

For a full list of the Six Habits - click HERE

Never, never, never give in – Allison Dorst of Pinks and Greens

Six Habits of Highly Successful Founders



#2. Never, never, never give in – Allison Dorst of Pinks and Greens

It is hard to single out any single entrepreneur for their grit and determination. Because, of course, it goes with the territory. However as an investor it is nonetheless impressive to see a founder who has bootstrapped themselves to $1mn/year+ in revenues learning the ins and outs of an entirely new business to along the way. This is especially so for Allison Dorst, a founder who was a banker for nine years and decided to learn ecommerce business from the bottom up ... and built Pinks and Greens in the process.

Needless to say I have a bias when it comes to the much maligned investment banker class having been one myself. Although, as I wrote last year, I genuinely believe that ibankers have an intensity of customer focus and timeliness that fits well in startup land. Quite rightly investors put a high premium on domain expertise and market knowledge. 

But in my view that expertise can be learnt and learn quickly especially by someone working it 24/7 who is in continuous learning mode and never gives up. A couple of years of that sort of domain expertise acquisition is a very powerful way to acquire the proverbial “unfair advantage”.

Lesson: Be super persistent and always be learning

For a full list of the Six Habits - click HERE

Be the Wizardess of Oz – Kathryn Minshew of The Muse

Six Habits of Highly Successful Founders

#1. Be the Wizardess of Oz – Kathryn Minshew of The Muse

As I explained to Ben Fischer as The New York Business Journal back in April, "As you're trying to start a company, in the normal course of events, a lot of very reasonable people wouldn't give you the time of day, so you have to find a way to make yourself the Wizard of Oz, in that you command more attention that is really justified by the substance." Or, as I put it in the context of Kathryn Minshew CEO of The Muse, The Wizardess of Oz. 

Hopefully Kathryn took that comment as a complement although frankly now it is looking dated. From the team of three co-founders hitting Y Combinator back in 2011 The Muse is now a team of over 20 and The Muse web site is approaching 2mn unique visitors/month. 

But I think the observation holds true … that in that early phase of a startup, especially when you are selling to skeptical enterprise customers, getting your own and the companies profile and credibility as high a possible is vital. Getting ahead of you startup skis so to speak. Then over time you can earn your way into that stature … and more.

Lesson: Smart startup promotion is a core skill, use it or lose it


For a full list of the Six Habits - click HERE

Six Habits of Highly Successful Founders


Six Habits of Highly Successful Founders


So what did I learn in 2014 from some on my start up investees? In this post I share are some of the things I have seen six companies I have invested in do especially well. 

Typically posts on what makes a great founder/entrepreneur expand on lists of keywords, most pretty self evident and also often contradictory when you compare different versions! 



Rather than repeat that exercise I tried to identify more concrete and actionable “habits” These are nitty gritty execution tactics and strategies that have taught me, as an investor and advisor, a lot of practical startup wisdom.

In no particular order here are my Six Habits of Highly Successful Founders:

1. Be the Wizardess of Oz – Kathryn Minshew of The Muse
Lesson: Smart startup promotion is a core skill, use it or lose it

2. Never, never, never give in – Allison Dorst of Pinks and Greens
Lesson: Be super persistent and always be learning

3. Pitch, pitch and pitch again – Erika Trautman of Rapt Media
Lesson: Pitching is a core function of the CEO - but only pitch as the real you

4. Build to scale, before you scale – Lisa Xu of NopSec
Lesson: Don’t just be hands on, be hands ahead

5. Win the game of “whack a mole” - Kelsey Recht of Venuebook
Lesson: There is always a new mole. Whacking it and moving on is a team sport.

6. JFDI - Julia Shapiro and Jules Miller of Hire an Esquire 
Lesson: JFDI - it’s as simple as that!