Starting a Company Is Hard But….

As a seed stage investor to young companies (and someone who has previously worked at a brand new startup), I know it’s hard. Really hard. The type of hard where you joke that if founders could properly calculate the odds of succeeding, no one would ever start a company!

Two recent blog posts have stuck in my head which focus on the exception focus, skill and luck you need to build a startup. The first was Jason Calacanis’ “You Don’t Have What it Takes,” which, as the title suggests, is a plea to the 99% of founders who Jason doesn’t think have what it takes to start a company. And there’s nothing wrong with making that choice. As Jason writes:

“You see, what I’ve learned after 25 years of doing this startup thing is that 99% of people simply don’t have what it takes to lead a startup — and thank God. Leading a startup is a brutal pursuit. Most days are a death march in which you work horrific hours under massive duress waiting for your chance … to join the 80% of startups that die off.”

The second was a reminder from an entrepreneur named Paul Smith that just because you raised funding, you can’t take it easy. In fact, you need to work harder. Also provocatively titled “Your Well-Funded Startup Is Already Dead,” Paul observes:

“This isn’t about working until you burn out. No investor wants to see a team implode. But as a founder, you must understand that your startup is your priority for the next five years. That means you won’t see your friends and family as often. It means relationships will suffer from time to time.”

Paul and Jason are speaking 100% truth and they both note that there’s no shame in not founding a company or needing to take a vacation to recharge. BUT…. these posts have been gnawing at me a bit and I can’t exactly put my finger on it. Starting a company – deciding to absorb that risk – should attract a self-selecting group of founders but I also suspect stressing nothing but the long odds, the sacrifices, creates a barrier to entry for entrepreneurs who don’t have role models or a support system around them.

I’d be really interested to understand how posts like these are understood by a white, male Stanford grad versus an equally qualified founder from a more underrepresented segment. How do we help potential entrepreneurs understand the long road ahead of them while letting them know there’s a support system to help them? Frankly, for the industry and for innovation, it’s better that 1% too many people start companies than 1% too few because you never know, you just never know. And maybe that first time doesn’t work but the second time does….

Ok, Here Are My Fall 2015 Calendar Experiments

Most of you will find this post boring so stop reading. Okay, for those still with me: while sharing a bunch of links around time management I offered to note some of the changes I’m making to my calendar, if anyone was interested. Well at least 12 of you said “yes,” so….

I do a twice-annual calendar refactoring, trying to break bad habits that I may have fallen into and also experimenting with a few changes that I believe could lead to a more productive and happier state. Here are a few examples of what I’m currently implementing across the three basic categories that I look to balance. These aren’t exhaustive statements about my 24/7 but rather tweaks, modifications and resolutions.

My Playbook: Get Better at What I Do at Homebrew

Problem: Projects which require 2-6 hours of work time never get done because there are no work blocks I’m setting aside of that length.

Solution: Every other Friday I’m going to try and set aside 12-5pm to work offsite on 1-2 projects

Problem: Homebrew events strategy was stagnating because the events I wanted to do were getting too big, expensive and complex

Solution: Going back to small, thematic, off-the-record dinners where 8-10 people (from portfolio and outside) get together to discuss a particular topic of interest. Do at same restaurant every time for logistical ease and price negotiation opportunity.

Grow the Pie (hw: my shorthand for being a good tech community member)

Problem: Value time in future lower than time today. Found myself agreeing to meetings 2-6 weeks out because calendar had space, only to be overwhelmed and out of priority when time came.

Solution: If I wouldn’t do it this week, say no. I’ll try other ways to help (over email, phone calls while I drive) but will need to decline more conversations which aren’t in service of our investments or potential investments. I still believe in paying it forward so will need to find other ways to scale. 

Problem: I commit to replying to any cold email at least once, but was increasingly replying just-in-time, which inappropriately raised the priority of these replies.

Solution: I now label and archives these and set aside 60m slots on Tuesday and Thursday nights to respond. So you’ll still hear back from me, just not always within 24 hrs, but hopefully always within three days or so.

Health, Energy & Sustainability

Basically some schedule changes to encourage me to start exercising again, pick up my kid from school more often and be a better husband :)

Yes, Let’s Ask Men in Tech About Being Dads


Every Once in a While, Shake Up Your Calendar

If your calendar accurately reflects how you spend your time then it’s a source of truth like no other. More than your words and more than your intentions, what you actually do each day is the ultimate statement of your priorities and values. Twice annually I make wholesale changes to how I approach scheduling my hours, days and weeks. It’s usually a combination of correcting bad habits or observations about mismatches between my goals and my effort. But I also throw in some experiments to test hypotheses, such as in 2014 making my default meeting time 30m instead of 45-60m.

If folks find it interesting, I’ll write up what I’m trying out now, but also wanted to share some resources to help you think about your own calendars and time.


Why My Kitchen Cabinets Could Solve Jet’s Cold Start Problem

receipts_2076021bI want to try Jet, the new commerce site which promises to be even cheaper than Amazon. What prevents me? The idea of having to rebuild my “list” – the things I order frequently from Amazon or pick from the shelves as I shop physical retail stores.

How could they solve this cold start problem? One way would be to let me submit a picture of my store receipt, or photos of my cabinets, freezer and refrigerator contents. Some OCR + Mechanical Turk and they’d be able to return me a digital list for my next order. Allow me to forward my Amazon Subscribe & Save email receipts (or just comb my inbox for Amazon receipts a la how Tripit can extract travel-related messages) and you’ve essentially got all the personal information you need.

Dropbox previously acquihired Endorse, a team that was working on receipt-based coupon redemption and market intelligence. Basically you could submit photos of your receipts and get rebates from CPG companies for buying their products. They were also obviously assembling a large taste graph for what consumers purchase, since that SKU level data is usually unavailable outside of the specific store’s databases. Having been part of the Endorse beta it was a bit too challenging to collect receipts every time and they were never able to reach the scale needed to prove to brands that it was a compelling channel to support.

Are my suggestions good ideas for Jet? Maybe, maybe not, but many types of businesses face cold start problems and you need to be creative in figuring out how to build new habits. There’s lots of information value in my cupboards and receipts (not to mention inbox) which today goes unused.

new story

What’s It Like Being a NonProfit in Y Combinator? Five Questions with New Story CEO Brett Hagler

new story

Y Combinator Demo Days are a unique event in Silicon Valley. 100 Startups and what feels like 1000 investors all chasing unicorn dreams. But what happens when you’re a startup that never plans to get acquired, IPO or even return money to your backers? A few years ago YC started admitting a small number of nonprofits each class who could benefit from the focus and momentum of startup thinking. Earlier this year I was impressed by, and donated to, Detroit Water Project, which helps pay off water bills for people who need assistance. This class New Story caught my eye – an organization building houses for those desperately in need. Now that Summer 2015 YC has finished, I caught up with New Story CEO Brett Hagler for a quick chat.

Hunter Walk: As a non-profit, how’d you decide YC was the right path for New Story?

Brett Hagler: We started New Story with a mindset to operate just like a for-profit tech startup. To us, there should be no difference in mentality. We built a disruptive model (just like all companies in the batch) and are using tech to scale. We wanted to learn from the best, therefore, YC was the perfect fit!

HW: Was there a particular bond between you and the other non-profits in the class? Between you and the non-profits from classes past? What lessons did they share?

BH: There wasn’t a bond that was unique between the nonprofits, at least in our experience. Since all of the YC companies are being guided by the same overarching principles like “do things that don’t scale” and finding product-market fit, the lessons we learned from companies weren’t differentiated by whether or not they were not for profit.

We have a big vision to turn tent slums into sustainable communities, and it’s encouraging to be surrounded by other companies with big visions that we can learn from and be inspired by.

HW: When you look at where New Story is today versus where you were before YC, what has changed the most?

BH: Our mindset has changed the most. We’ve funded 91 homes ($546,000) during YC, and the cause was the audacity to think bigger, along with the discipline to reverse engineer big goals into weekly and daily goals.

We originally told Kevin Hale that we wanted to fund 50 homes during YC (which would’ve been crazy growth for us), but he challenged us to do 100 homes. Our team was speechless (literally) when Kevin set this challenge, but it sparked the 100 Homes in 100 Days Campaign. We’re currently at 91 homes in 84 days.

HW: Do you see a shift in the culture of the tech community to want to donate time and dollars to causes that matter to them? Sometimes founders get accused of using SF as a playground, buzzing between hot bars in Ubers but ignoring the complexity of the city around them.

BH: The tech community needs nonprofits they can believe in. Nonprofits that are innovating, disrupting status quo models, using tech to grow efficiently, and focusing on building a great product with a formidable team.

We’ve had great support from the tech community because they believe in our transparent, tech-powered model. They can see EXACTLY who they help and know that 100% of their donation will directly build a new home.

HW: How can someone get involved in New Story and contribute?

Start a fundraising campaign. You can “donate your birthday” to help build a home.

Meet a family and help fund their home or fund a full home yourself ($6k/home)

Invest into our operations. This is a private group of donors known as “The Builders” that act as our angel investors. Brad Feld is an example of one of our Builders. Email me, brett@newstorycharity.org, for more info.



Bedford police creating saf (7)

Public Spaces: Towns Creating Safe Zones to Meet For Craigslist Transactions

You want to buy or sell on Craigslist but worried about meeting up to complete the transaction? Towns are creating safe “exchange zones” with ample lighting and video surveillance to facilitate peer-to-peer commerce. Often in concert with the local police, they’re a fascinating example of the physical world shifting to reflect the needs of the digital one. Are they an aberration while we solve for trust online (craigslist notably lags in this area since they don’t require any real identity in their listings)? Or should each municipality think more deeply about how town squares, libraries and other public institutions can evolve.

Bedford police creating saf (7)craigslist-crop