Tweet Disclaimer

There’s been a lot of discussion recently about when disclaimers should accompany blog posts, news articles, etc. Since I’m a totally above-the-board kind of guy, when reading my tweets, please be aware that one or more of the following disclaimers apply:

I invested in the company or am looking to invest in the company (or the company turned down my investment and thus they are morally corrupt liars who deserve to fail).

I am friends with the founder or multiple employees. Basis of friendship may include classmates, former colleagues, awkward social interactions but we’re in the same general friend circle so we need to pretend we’re buds, blood relatives (click here for 23&Me results to see if we’re relatives).

The brand mentioned has sent me something for free and while they didn’t ask for anything particular in return, I found it odd they included a hashtag in the note. Or I’m hoping the brand mentioned will send me something for free. #SellOut.

@HunterWalk is actually a pseudonymous account representing a much larger group of people. While this explains how I fav so often, it also makes this disclosure statement difficult because I’m one degree of separation from 75% of Twitter (and the other 25% are bots).

I may be trying to gain the attention of someone in hope they will retweet me and if they don’t, will deep fav several tweets from their timeline history. If they still don’t react I may simultaneously send them friend requests on the Top 100 social networks. After that, it’s Single White Female.

If I seem to be getting into a Twitter Fight, I may also be in a DM conversation with the same person strategizing how to gain attention. This doesn’t include @rabois. I mean, he and I DM all the time but it’s the only DM stream I have that’s actually nicer and kinder than our public back and forth.

I repeat, I am not Startup L Jackson.

When you see people link to a Techmeme headline in their tweet they’re obviously trying to get that tweet included on the site. I never rarely do that.

If I’m tweeting with journalists please be aware I classify reporters into three camps: those who I’m friends with and who also happen to be reporters, those who are reporters that I’m friendly with and those who I don’t trust. Always remember that middle bucket is looking for a story. And if you’re a reporter reading this, you’re totally in the first bucket (love ya, cover my companies please).

New Homebrew Investment: Q

Today Q publicly announced their seed financing which we were fortunate to lead. Excited to work with the Q team

Q: Running a Business is Hard. Running Your Office Shouldn’t Be

If you’re a small or medium-sized business, there are more tools than ever to help you manage virtual operations: from payroll and benefits administration to accounting to technical infrastructure. And increasingly, all of those services are available via the cloud, to be monitored and run via PCs or smartphones. Yet somehow managing the physical infrastructure of your office is still a mind-numbing, time-consuming chore. It no longer needs to be. Meet Q. Q provides office cleaning and other smart services to help your office operations run smoothly – all delivered via an iPad that’s installed for free in your office.  

The Most Difficult Question I Ask Founders

One of the things I like least about seed stage venture is the compressed amount of time to get to know a new founder during fundraising. “Solutions” include pre-emptive activities such as building long-term relationships with future founders or mentoring at incubators to meet teams pre-seed, plus getting really good at reference diligence, but we still rely upon accelerating the “would we work well together” discussion during fast-moving investments. So each seed investor comes up with their own “minimum viable relationship” threshold, usually a factor of their investment strategy/velocity, how quickly they can get comfortable with someone and their skill in asking questions which matter.

One question which matters to me is the “why” of your startups, especially as it relates to your longevity as a founder. The most difficult question for some founders is “why do you want to spend 10 years of your life working on solving this problem.” Whoa, 10 years? Who said anything about 10 years? I’m just trying to raise some money, hire a designer and find product market fit!!!

Yeah 10 years is a long time. And that’s the point. Most startups won’t make it 10 years and the question doesn’t necessarily assume the founders will be in the same roles the entire journey. But my bet is the stronger your flinch to the question, the shorter the roadmap you have in your head and the smaller, less urgent, less valuable the problem you’re trying to solve. And I want founders with long roadmaps solving large, urgent and valuable problems. I’m still iterating on this question’s phrasing. I sometimes say “why do you want to spend several years, and hopefully many more, of your life working on this problem.”

The answers which resonate most with me have some combination of:

  • I’ve been working on this already (ie everything I’ve done to this point makes me ready to win here – doesn’t mean industry expertise but means some combination of skills and assessment of why you’ll succeed)
  • A definition of success that can only exist at that scale, whether it’s the complexity of the problem, the business they want to build or the organization they imagine building
  • Acute awareness of what needs to be done in the next year to move forward at highest velocity. It’s the long and the short. The founders know what it looks like in the near term and in the longterm. The middle – the path – is what they figure out as they go.

I may not enjoy the compressed timeframes to get to know teams but figuring out how to use my time with them effectively and efficiently is a key component of being a good investor.

Oh, and here’s the Why of Homebrew.

triest hulk

Jonathon Triest of Ludlow Ventures: “VC Done Right” (and in Detroit)

triest hulk
You meet interesting people backstage at conferences and in 2013 that included Jonathon Triest who started Detroit-based Ludlow Ventures. Despite the seemingly not so humble tagline (“VC Done Right”), I found him to be a ‘grow the pie’ guy who excitedly looks for opportunities to help entrepreneurs and collaborate at the seed stage. In that spirit, asked him to share some background and perspectives.
Hunter: We met last year and i’ve been impressed by your eye for interesting companies but I’ve got no idea how Ludlow Ventures got started. What’s the origin story?
Jonathon: Oh man. I’m a fortunate guy. This is not your typical VC origin story. I was not an early employee of Google, nor did I exit a company for 6 zillion dollars. Let’s back up. I was the furthest thing from a good student. By some miracle I got into the University of Michigan, and soon started passing classes by developing strong relationships with my professors rather than living in the library. Although never medically confirmed, I’ve always been convinced that I have numerous learning disabilities, so I’ve never been able to sit and focus for long stretches. On a positive note, my inability to sit forced me to learn about people and building relationships. Josh Howie (@joshxhowie) just tweeted “It was only after Attention Deficit Hyperactivity Disorder was shortened to ADHD that its sufferers were able to focus on their condition.” That pretty much sums me up :)
I’ve always had a passion for photography, so while at U of M I joined the Michigan Daily (the campus student publication) as a photographer. I’m dating myself here, but this was during the transition to digital. In fact, most of my early work there was done by pushing and developing film manually. I fell in love with the post production work I was doing and my interest in photography started to subside. I taught myself the Adobe suite, and one thing led to another. I found myself doing a lot of design work. There was really a need for designers at the time, so I figured “hey, I’m ok at this. It holds my attention, and I can charge a boatload for a silly logo (long gone are those days.) I opened Triest Group a small design boutique and moved to NYC.
It was there that I started doing strange things to get in front of people I wanted to meet. My first client was a company that made really cool headwear for men. They ignored my emails, so I found out the CEO was leaving town to attend some fashion conference in Brazil. When I knew she was out of town I went to her offices as if I had a meeting planned. Chutzpah. After her assistant was done apologizing for the “miscommunication” I told her I’d leave my mockups in the CEO’s office. The CEO returned to my vision of her brand plastered to every wall in her office. I could have gotten a nastygram, but instead got hired… client numero uno was in the books. I continued to do more branding and design work for clients and over time found myself working for mostly cool tech startups. I was smitten. No turning back. Moved to Jerusalem, Israel, then Atlanta where my wife was in medical school, and finally moved back home to Detroit when we started having children, all the while building up a good book of design business for tech companies.
As the years progressed I found myself less interested in design and more interested in the business side of the startups I was working for. I made the decision that someone with the attention span of a gnat would do better on the investing side of the table rather than operations and began pitching friends and family on the idea of starting a small fund. It remained just that, an idea. No one had much faith that I could effectively invest their hard-earned capital (and rightfully so, I had no formal training, a pathetically small network, and half-baked strategy.) So then I did what any self-respecting, eager beaver would do… beg. I basically made myself so annoying that in an attempt to get me to leave them alone a few family members dedicated a modest amount of capital to help me get the first “fund” (no outside LP’s) running. I crowdsourced a logo, named the firm Ludlow after the street I grew up on as a kid, and made myself some business cards. Game on.
I went out west and started knocking down the doors of the most reputable investors that I had been reading about. Most of those doors were reinforced with steel and never budged, but a few opened. Brad Feld (Foundry Group) and Naval Ravikant (AngelList) were (semi) receptive to the idea of mentoring me, and I’ve made them regret that every day since.
There’s more… but that’s probably way more than you were interested in.
HW: You’re in a wide range of interesting companies – how do companies usually hit your radar?
JT: We seek out incredible people bringing BIG ideas into fruition. Our ears are always to the ground, and the second we hear of an impressive personality, we do everything in our power to meet with them. Hunt them. Make is so they have trouble going to sleep at night without taking our money. Sounds kind of creepy. But hey… we’re kind of creepy.
Our inbound deal flow looks like this in order of priority:
1) Companies we read/hear about and hunt down.
2) Warm intro’s from entrepreneurs we’ve previously funded.
3) Warm intro’s from VC friends (that’s you Hunter!)
4) Angel List (an awesome place to discover startups.)
5) Cold emails (should be noted that we’ve never invested in a cold intro… not to say it will never happen, but it hasn’t happened yet.
HW: Sooooo Detroit VC scene. What’s that like?
JT: It’s Growing. We moved our offices to Downtown Detroit nearly three years ago and the transformation has been spectacular. There’s LOTS of growth still needed to make it sustainable, but if the trends of the last three years are indicative of the future, we’re in a good spot.
It’s a small scene. Everyone knows everyone. More importantly, like true midwesterners, people are always willing to help each other. When a Michigan company wins, we all truly feel like winners. That’s not something I’ve seen outside of Detroit.
HW: Is it getting more competitive for early stage VCs like yourself? Are you finding sharp elbows working with larger VCs? Get screwed out of pro rata recently?
JT: No comment.
Screw that. Ya, we’ve gotten screwed out of some later rounds by larger VC’s. But, to be fair, of the 20+ companies we’ve funded that have gone on to raise larger rounds, it’s happened twice. While not the norm, it still stings. We made a bet on these teams when the fancy-pants VC’s weren’t ready to back them. Then they prove themselves and we get diluted. Still figuring out how to send them flaming bags of poop.
HW: What’s something you believe that might be contrarian or a less frequently held belief among other investors?
JT: That the most important qualities in a founder (or founding team) are not technical skills or business expertise, rather the ability to communicate clearly, passionately, and effectively. If someone can explain what they do clearly in the first 30 seconds, there’s a good bet I want to learn more. Most people are boring. It sounds rude to say, but it’s true. At Ludlow, we are always looking for the unique individuals that captivate and motivate those around them.
(thanks to TechCrunch from who I stole the Green Jonathon graphic)

Dear Twitter, I Want to Be Your Spam Sheriff But Need This One Feature

I love flagging spam on Twitter. And reporting ToS violations on Etsy. And spammy comments on WordPress blogs. Basically I’m the guy willing to help pull weeds and fix broken windows to maintain order in my community. Having worked on abuse tools at YouTube I know how vital user flagging is to enforcing community guidelines within these platforms. But the vast majority of these systems fail in one important way: they never close the feedback loop with the user who reported the issue.

No “Thanks Hunter. Because of your help, we’ve closed 124 spam Twitter accounts”

Never a “Hunter, the comment you flagged on 10/24/14 has been removed. Thanks for keeping YouTube a positive community!”

Somehow the gamification trend bypassed community support tools. The arguments against providing these type of responses usually come down to:

a) spammers will use this information to reverse engineer flagging algorithms

b) if a flagged piece of content isn’t removed, the person who reported will be pissed so why rub it in their face

Neither of these ring very true for me. Sophisticated spammers already have plenty of ways to test spam/abuse detection systems using bots, APIs, etc. And there are clearly ways to provide generalized feedback to the flagging user without reporting back decisions on an item by item basis. And for (b), I’m more pissed feeling like my flags are just being thrown into a black hole. Plus, feedback helps not just motivate but also trains the reporting user.

So my POV is the best community support systems include a feedback look for the users who proactively report violations. I believe Secret does something like this for flagging violating secrets. It’s time the larger platforms did similar.

Update: yup, here’s what Secret does



Hello, My Name Is… (or, What I’m Surprised is Missing on Square’s Receipts)

Square’s Order ahead app (and their deprecated Wallet) humanize transactions by supplying the merchant with my name and photo. Made me always feel like a regular when, with Wallet enabled, I could just order my coffee and have the person on register say “Thanks Hunter, you’re all taken care of!” Especially with smaller local merchants, the ability to create intimacy and relationship is a competitive advantage against chain stores and online retailers. Jack Dorsey has also spoken at length about redesigning the receipt to be something more useful, which you already see in play with the merchant feedback survey (smile or frown).

So I’ve always found it a bit surprising that Square focuses on the merchant identity but not the employee who actually helped me. Maybe it’s their roots as a tool for sole proprietorships where the two are one in the same, but with the example from Four Barrel below why doesn’t it tell me the Barista’s name? Get individual employees to create their own profile/bio and let me know that “Paul” hopes I had a great coffee. That Paul’s favorite band is NOFX. And that Paul’s appreciates my dollar tip because he’s currently working his way through a Master’s degree. A real chance to turn the employee into a person.

In general it’s my belief the PoS/electronic currency mediums of the future will do a better job of making it feel like people are transacting with one another. Not just two electronic machines exchanging currency for goods or services.

Any retail PoS systems doing this in interesting ways (Venmo’s social feed is an example in p2p)? Any downside for Square or others (besides just potential low prioritization among a long roadmap)?