So you’re thinking about a “things to do” app

AKA “events”, AKA “local discovery”, aka “help me find things to do in my free time”.

TL/DR. Just Don’t. Please, I’m begging you.

As one of the founders (and CEO) of goby, a local “recommendation engine for things to do”, I get approached fairly frequently (seems like every few weeks) by entrepreneurs who want to work on this problem. In the interests of saving both of us time, I decided to write down the high level reasons why this is a really bad idea. Read this first, then we can chat if you still want to try.

Before we get started, a few caveats. This advice assumes you’re trying to doa venture-backed unicorn, need to raise money to pay your salary, and hence need to scale. If you’re doing a bootstrapped personal project where you make a few bucks, much of this may not apply. Second, I don’t really even want to hear about your product. Even if your product is amazing, it doesn’t matter. You won’t make it. The problem in this market isn’t the product, it’s the market.

The challenge here is not to make a great product, it’s to get scale of users. If you’re doing a venture-backed startup, you need MILLIONS of users for this to work. Here’s why you won’t get them:

  1. It’s not a daily use case
  2. Most people don’t actually have free time
  3. You need to scale geographically as well as topically
  4. It’s hard to get good data
  5. Competition (I have a Graveyard of ~200 companies who’ve tried).
  6. No clear path to monetization

If you’re unconvinced, you can read a bit more detail below about these various factors. But trust me, I’m right.

Is this a real problem for people? Yes. Are experiences valuable? Yes. Is this problem worth solving? Yes. It just won’t be a startup.

In a previous generation, this problem was solved by Newspapers. They had a “metro” section that highlighted cool things going on. They already had an audience, they had local knowledge, they just delivered some extra value. The future version of this problem will be solved by a brand that already has an audience. Maybe a platform like Facebook (already the biggest events database on the planet), or a Yahoo/AOL/some other portal, or by a brand working in a bigger associated space (Foursquare? Twitter? AirBnB? Uber?).

OK, so you’re unconvinced. Keep reading.

It’s not a daily use case.

I’ve written about this at length elsewhere, but because of the way people discover, test, and re-use new apps, unless you have a near-daily use case, people just forget about you before they need you. A similar take from Ben Yoskowitz.

Most People don’t actually have free time

Who is your demographic for this? Young urban singles have free time, they like to go out at night. Married people with kids — their weekends are spoken for. Mow the grass. Go to the soccer game. Run errands. Get up Monday morning. It’s tempting to think there’s millions of people sitting around bored, because it happens to all of us at some point. But most of the time, most of the people don’t have this problem. It happens once a month if you’re lucky. And then, many people will just decide to stay in and watch Game of Thrones.

You need to scale geographically as well as topically.

In order to get millions of users, you can’t just do one city. Not enough audience. So, that means you need data for New York, Boston, LA, Raleigh-Durham, Atlanta, Moab, …. and you need to cover different topics for different demographics (nightclubs vs family-friendly events)…unless you have some serious tech (we had semantic web crawling from MIT @ goby and still struggled), you won’t be able to get this data easily. Which leads to:

It’s hard to get good data.

Unfortunately the data is distributed — Facebook events, Wine tastings on location restaurant websites, concerts on Ticketmaster,….it’s all really spread around. There’s no centralized place to get it. Not only do you have to cover lots of geographies, you have to cover lots of topics. Jazz, Hiking Trails, beaches, Comedy, Family Friendly book readings, the list goes on and on and on. If all you do is aggregate some events from Ticketmaster, nobody needs you — they already have Ticketmaster! Which leads to….


You started work on this because you think it’s a problem nobody’s working on or solved. Guess what: I keep a list. I call it The Graveyard. There’s HUNDREDS of startups who’ve tried and failed to solve this problem. Some really great services: goby, Sosh, SCVNGR, Diddit, Hotlist, Banjo, Sonar, Whrrl, Spindle, Schemer by Google, Eventful, Zvents, Upcoming (now returning, believe it or not!!). This runs everything from one person in his/her basement to apps from biggies like Google. Nobody lasts more than a few years. When that happens, it means something’s wrong with the market, not the companies. Can you explain why you’ll succeed when all these other good folks failed?

Now, in some specific big areas there’s players: Ticketmaster for music, EventBrite for professional events, and some others. But they are the exception, and worse, if your app is great at music, then you have to swim upstream against a brand like Ticketmaster.

(and, you’d better have a web site, an IOS app, an Android App, and soon, a chat bot interface :)


Finally, it’s very unclear how to monetize this space. Ads? Forget it. Until you have 2 or 3 million monthly uniques, you’re not getting anywhere with ads. Affiliate revenue? Most of the things that are purchasable are being sold by the Ticketmasters of the world — and people would rather buy from them than you.

A lot of big problems you have to solve.

Here’s some required reading of some post mortems and other folks’ thoughts on this:






Getting your startup’s first 500 users

There are many articles about growth hacking out there, but they tend to focus on startups that already have some level of traction. But what about those really early days when you have no idea where your users are going to come from? How do you get to your first 500 or 1000 users?

Paul Graham famously said you have to “do things that don’t scale” in the early days. Rather than adopt a strategy that works for tens of thousands or millions of people, do something that works for tens or hundreds of people.

My site, The Hawaii Project, is a personalized book discovery engine, created because existing solutions simply don’t work for finding great books to read and keeping track of your favorite authors. However, it violates one of my basic rules for B2C startups — it doesn’t have a daily use case. (Most people don’t look for new books to read every day ). I’m knowingly violating one of my rules because this project is near to my heart, but it makes for tricky customer acquisition!

I built my positioning hypothesis for the product early on, following the sage advice of Michael Troiano. (which goes something like, “For avid readers looking for great books to read, The Hawaii Project recommends high quality, personally relevant books you’d never find on your own because we track hundreds of hand-selected sources of great books and match our findings to your interests.”). Which is too long. But that’s where I started.

Because the books space is interesting and complicated, I build a stakeholder map — everyone who might be interested in what I’m up to. That includes Readers, Book Bloggers, Book Clubs, Authors, Publicists, Publishers, Bookstores, Libraries and Librarians, Literacy non-profits (we donate 10% to them), Journalists and the startup community. I crafted pitches for each of these communities.

I highly recommend Traction, which provides a well-thought out framework for thinking about customer acquisition channels.

Traction: A Startup Guide to Getting Customers

Most startups end in failure. Almost every failed startup has a product. What failed startups don’t have is traction — real customer growth. This book introduces startup founders and employees to the “Bullseye Framework,” a five-step process successful companies use to get traction.

With that in mind, here’s my path to 500 users — what tactics worked and what tactics didn’t. By users I mean people who signed up for an account on THP — I don’t count simple site visitors (of which there are many more).

First, let’s look at the chart of user acquisition by date, with the key milestones. As you can see, much of it is “slow and steady” growth — with some occasional spikes.

I started acquiring users before I launched, by running a private beta program. Most of those were people I knew — friends & family. For better or worse, from there I moved to doing a Kickstarter, pre-launch. The Kickstarter did not reach its goal so I didn’t get money, but it did generate a fair bit of early press and additional users.

In broad strokes, 15% of my first 500 users are friends and family. 5% are identifiable as “friends of friends” where the product spread without my involvement. 5% are people I didn’t know but networked to for business reasons, and who subsequently signed up. The remaining 75% are people I don’t know, who came in through various activities discussed below. About half of them came in as part of the broader Kickstarter initiative — press, social media posts and the like. Many of the people who signed up at launch were queued up from the Kickstarter campaign and waiting for entrance.

Some pre-launch, early tactics that worked:

  1. Friends and Family. No secret sauce here. These are the people who want you to succeed — all you need to do is ask.
  2. Your professional network. I shamelessly spammed my LinkedIn connections (about 1000 of them).
  3. Kickstarter & related Press outreach
  4. Social Media. A particular success for me was live-blogging my Kickstarter campaign on LinkedIn, which generated a large number of Kickstarter pledges and email list signups, who converted to registered users when we launched, and garnered me ~1500 followers on LinkedIn. I used LinkedIn because that’s where my biggest network was. Choose your biggest / best platform, but keep in mind you can’t just spam them — you have to produce content on a frequent basis, so consider what kind of content you’ll be making and where it most naturally resides. A bunch of posts about startup marketing don’t seem to fit on Facebook.

Those are classic jump-start techniques. Even though the Kickstarter was a lot of work, and didn’t raise funds, it provided a reason for press outreach and a framework for launch that people could embrace.

Since the Kickstarter, there’s been three major “events” that generated significant upticks in users:

  1. The Launch — having done a lot of work with press and email-list gathering, when I took The Hawaii Project out of private beta, and opened it up, I had a good email list I could blast to — many of those people signed up.
  2. I invested a lot in LinkedIn, where my network is strongest. As a result of live-blogging my Kickstarter on LinkedIn, a series of posts I wrote (mostly not directly about The Hawaii Project) got featured by LinkedIn editors. One post garnered 25,000 views, another 5,000 views — some of those readers turned into THP subscribers.
  3. HackerNews. I posted a “Show HN” post on HackerNews. I got some friends to bump it, it picked up steam and snowballed into 100+ users — 20% of my first 500! I don’t know what caused it to catch fire, but the community was really helpful and engaged— I got some great feedback in addition to signups. I am sure many of that community were “tire kickers” rather than just average book readers, but it was very helpful! (A similar attempt at Product Hunt sank without a trace — YMMV).

More along the lines of “doing things that don’t scale”, some other activities that yielded early results:

  1. Email “Spam” — I found mailing lists of librarians online, web-scraped them for the email addresses, and sent every librarian in Massachusetts an email about the campaign.
  2. Book Clubs — I visited a number of book club meetings and signed people up. One of them is using THP to source all their reading choices. While it doesn’t scale, it did generate users — I also realized my product wasn’t a complete solution for book clubs, a topic I plan to return to in future.
  3. Bookmarks — I printed up Bookmarks with attractive “book on a beach” imagery and THP website and contact details, and hand them out at a drop of a hat. (After the first version, I put a trackable URL on them so I can see visits if people type it in). Decent (not high end) bookmarks cost about $0.50 from VistaPrint, so after factoring in conversion rates, the Customer Acquisition Cost is high — but it’s great branding for events, and doubles as a unique business card.
  4. Partnerships. I partnered with the Nahant Library to embed The Hawaii Project in a frame in their website, which generated ~500 visits and a number of subscribers (plus some revenue!).
  5. A side project. As part of the CODEX hackathon, I built BookPlaylist (a bastardized THP where you can build Spotify music playlists to go with your favorite books) and cross-linked it to THP, which generated customers.
  6. Quora. Recently I have started answering books-related questions on Quora, and including links to The Hawaii Project for books I mention. So far, when I answer 2 or 3 questions a day for a week, I pick up 2 or 3 people a day for that time, pretty much a 1:1 ratio of answers to subscribers. Not super scalable but it seems to be reliable and repeatable. It’s now part of my day.

Longer term investments that may or may not pay off:

  1. Social Media Platforms and Content Marketing. I’ve been running a twitter account since I started work on the project, long before I even had a private beta (come follow us!). I tweet out interesting books every day, and have about 700 followers. Probably 50% of my followers appear to be authors, which is an interesting dynamic I hope to make use of some day. I run a Medium account which doesn’t seem to help much. I have a Facebook page which I don’t have time to manage — it gets views but I don’t think generates users. Most every blog post I write gets posted to LinkedIn, my personal blog, my personal Medium account, The Hawaii Project on Medium, and Twitter. The jury is still out on whether my Twitter time investment is really going to pay off.
  2. SEO. I saw the power of SEO with goby, where at peak we were pulling 1M+ monthly visitors from SEO. But SEO takes a LONG time to develop and so far my SEO traffic is a trickle, not a flood. But I’m a firm believer in getting this right and have invested a fair bit in SEO (probably worthy of a separate post).

I also tried some tactics that I thought would work very well. And they didn’t:

  1. Book Bloggers — I hypothesized that Book Bloggers, because they need things to write about, and love books and reading, would naturally want to write about The Hawaii Project. I wrote to about 20 of them, and heard absolutely nothing back. I believe there’s something there but early experiments weren’t encouraging — I haven’t found the right angle yet.
  2. Startup Events — I have a rule that I will talk to anyone who wants to listen, about THP, and I’ve been fortunate to speak at a number of startup pitch events. They’ve all been useful for various reasons, but none have led directly to significant signups.
  3. Author outreach — I hypothesized that Authors would want to help promote their books and would write about THP. Many of my twitter followers are authors. I’ve written to many (authors are surprisingly approachable, even famous ones). I’ve had many good conversations but it’s not turned into much in the way of users.
  4. Bookstore outreach — while it’s more of a stretch, I got in touch with a number of bookstores, in hopes of cross-promotion. Had a few interesting conversations, but in the end, we couldn’t connect the wires on their offline experience and my online experience. And most of them view themselves as being in the book recommendation business, interestingly, especially the “Indie” bookstores.

I also ran a variety of tests on paid acquisition, primarily Google and Facebook ads, so that I had data on cost of acquisition on those channels — they are scalable, if expensive. So far cost of acquisition significantly outpaces customer lifetime value, so I can’t just “arbitrage” my way to success, unless I find a way to reduce the ad costs.

In summary, there was no “one thing” that did it for me. I invested hard in “friends and family” and my personal network, and I tried many things, looking for things that showed promise. And kept at it. I invested hard in LinkedIn, because that is where my network was the largest, and it paid dividends. I followed my mantra of “Everything is Practice”, online and offline, kept trying things, and found a few hits and even more misses.

You should not wait for lightning to strike — invest in getting new customers every day, and plan for the long haul. I haven’t found the repeatable, reliable, scalable customer acquisition strategy, yet. Rome wasn’t built in a day.

The Travelers, by Chris Pavone

For a long time, I’ve wondered about how to characterize the difference between a spy novel and and a spy thriller. After reading a review copy of Chris Pavone’s The Travelers, I think I can now express it precisely. Both have secret agents, intelligence agencies, dead drops, tradecraft, double-crosses and other staples of the genre.

It’s all about the plausibility of the events. In a Le Carré novel, everything is completely plausible. No James Bond unrealistic derring-do. No jumping out of airplanes without a parachute. No complete civilians discovering crazy secrets and getting pursued by mysterious strangers. Just real people betraying something or someone, or trying not to.

The Travelers: A Novel

A pulse-racing international thriller from the New York Times bestselling author of The Expats and The Accident It’s 3:00am. Do you know where your husband is? Meet Will Rhodes: travel writer, recently married, barely solvent, his idealism rapidly giving way to disillusionment and the worry that he’s living the wrong life.

Which puts Chris Pavone’s thoroughly enjoyable The Travelers squarely in the Spy Thriller camp. It has many elements you’d find in Le Carre – skepticism about the nature and motives of Intelligence agencies, a morally grey world view where most everyone is a bad guy of some sort. But most of the book is an adventure, a fun but not very plausible one.

The Travelers’ is Pavone’s third novel, after The Expats and The Accident. He specializes in “normal” people (who often turn out to be not that normal), getting caught up in intrigues. Will Rhodes is a not-very-sympathetic character – a newly married travel writer with a wandering eye and questionable morals. He’s married to Chloe and working for Travelers magazine, with operations around the world and activities that might be more than just writing articles….and Chloe might not be who she seems either…before long Will’s made some bad choices, and events hurtle him from New York to Paris to cabins in the forest of Iceland to Ireland to Yachts in the Mediterranean to …well the book is so peripatetic that the section headers are location names.

If you’re looking for a great thriller, The Travelers will keep you entertained for hours. If you’re looking for deep insights into the human condition, you might want to head for Le Carré or Graham Greene.

I received a free copy of The Travelers through LibraryThing’s wonderful Early Reviewers program.

The Last days of Magic by Mark Tompkins

The Last Days of Magic is a quasi-historical fantasy set in Ireland. Drawn from the legends of Ireland and from (believe it or not!) the Dead Sea Scrolls, The Last Days of Magic tells the story of the Nephilim, the hybrid offspring of angels and humans, and the Sidhe (“shee”), the Irish faeries of whom much has been written.

The Last Days of Magic: A Novel

An epic novel of magic and mysticism, Celts and faeries, mad kings and Druids, stalwart warriors and the goddess struggling to reign over magic’s last outpost on the Earth Aisling is a goddess in a human form, born to rule medieval Ireland and reunite the earthly realm with the Middle Kingdom-home to powerful faeries.

I wanted to like this book. No, I wanted to love it. As someone with a lifelong interest in Druids, Faeries, and books like The King of Elfland’s Daughter, The Mabinogion and Thomas the Rhymer, I was looking forward to a magical tale of otherworldly beings. And this book tries so hard. The erudition of Mark Tompkins is beyond question, and his passion and love of this subject matter is evident on every page. Faeries, Nephilim, Sidhe, Gnomes, Brownies, Sluaghs, Pixies, Fire Sprites, Leprechauns, Dryads, Woodwoses, and other creatures drip from the pages.

That’s kind of the problem. Every time the story works up a bit of momentum, we stop for a diversion into another creature, another king, another tribe, another history, and by the time that’s done, you’ve forgotten what was happening. I’m surprised an editor didn’t rein this in.

If you are deeply interested in the history and lore of faeries, you will find this book interesting and informative. If you’re just looking for a good historical fantasy with Druids and Faeries, there are easier ways to get it.

(I received a free Advance Reader Copy from Edelweiss in return for an honest review).

Your first Oahu hike


Your first Oahu hike

So, you finally made to Hawaii. Magic. And you want to go hiking on Oahu. There’s a surprising number of options. As someone who’s been hiking the island for decades, here’s my guide to deciding on your first hike, whether you are a beginner or a seasoned mountain climber. It (somewhat) assumes you are a tourist or visitor, and you’re staying in Honolulu. And I’ve left out a lot of details, you can Google the details of any of these trails for directions and the like.

Easy/Kids: Lanikai Pillbox Trail, Diamond Head, or Makapu’u Lighthouse.
Intermediate: Lulumahu Falls, Aiea Loop Trail, or
Advanced: Kuli’ou’ou or Olomana.

Easy Trails

Are you a relative beginner as a hiker? Want some great views without too much work?


Get yourself to the Lanikai Pillbox Trail. A short, 30 minute climb to some WWII pillboxes, concrete bunkers used for lookouts.

If you’re not staying on the windward side (few do), then make a day of it, combine it with a trip to Kailua Beach and a meal in downtown Kailua.

Pros: Short (30 min), Views (out of this world), Safe (wear real shoes though, don’t hike in your flip-flops (or “slippas”, as the locals would say — a friend broke an ankle as the trail is very eroded in spots).
Cons: You will be on this trail with a hundred new friends. Seriously. About 1000 people a day hit this. Don’t go on a weekend.

2. Hit Diamond Head. Another short (but steep) climb. Much of the “trail” is really concrete stairs leading to the lookout. But the views of downtown Honolulu are hard to beat.


Pros: Easy access from Honolulu, Awesome views. Doesn’t take long.
Cons: Crowded. Lots of concrete and stairs.

3. Makapuu Lighthouse trail

The Makapu’u area is awesome. Makapu’u beach is one of our favorite beaches on the island. Mostly a locals beach, great waves for bodysurfing, and not too crowded. The Lighthouse hike is an easy stroll with amazing views. It’s easily accessible from Honolulu (30 minutes from downtown), or from the Windward side. The trail is mostly paved, and you’ll get a amazing views of the famous Lighthouse as well as the entire windward shore. Do yourself a favor and combine this with a stop at Makapu’u beach and lunch at Keneke’s, a local plate lunch shop.


Pros: Quick & easy, awesome views, only “moderately” crowded.
Cons: Mostly paved. Somewhat crowded.


  1. Lulumahu Falls

2016-02-15 17.59.52-1

Lulumahu falls are also easily accessed from both downtown Honolulu and and the Windward side.

Head up the Pali Highway, near the top you will see a bunch of cars parked in a dirt area, right where Nuuanu Pali Drive runs into the Pali Highway. There’s an entrance there to the trail. Just follow the people :). The trail to the falls will take you maybe 45 minutes (assuming no wrong turns — the trail is not extremely well marked). The trail is ok for smaller kids who like to hike. If you have a bit of extra time the bamboo forest and the ruins of Kamehameha III make for an Indiana Jones style experience. To find the path to the ruins, stay to the right as you come into the bamboo forest. There will be a side trail (looks a foot or two wide) that starts a gap in the bamboo. Just follow it west through the bamboo and you’ll find it eventually :)).

Pros: Indiana Jones. Waterfalls. Nuff Said.

Cons: Can be crowded. Not hard to get off the trail. Not a sanctioned state trail, but tons of people on it.

2. Aiea Loop Trail.

2014-06-16 15.38.12

Pros: An ancient Hawaiian heiau (religious temple built from rocks). Gorgeous hawaiian Ohia flowers. A commanding view of the H3 highway and Halawa valley. A lost WWII bomber (I’ve not found it —  yet — but it’s there). Relatively flat, 5m round trip hike.
Cons: It’s not much of a workout, pretty flat. But fun


  1. Kuli’ou-’ou Ridge Trail


This trail is a workout. You start in a Honolulu neighborhood and end at the top of the Koolau mountain range, looking down into Waimanalo, with commanding views in all directions. Along the way you’ll go through a number of different “zones” of differing vegetation.

Pros: Great workout, amazing views, high quality trail.
Cons: A stairmaster section at the end. But it’s worth it.

2. Olomana

IMG_8314 copy

Probably the best known Windward side hike. It’s not for the faint hearted. You’ll climb 1600 feet up a knife edge ridge, climbing with the assistance of ropes for 10–15′ in a few places. There are three peaks. The first is a workout but doable. The 2nd peak is not too much further, but you don’t get that much extra out of it, so I’d skip it. Don’t go to the 3rd peak. People die there. About once a year. Including experienced hikers. Just don’t.

Pros: Great workout, Amazing views, easily accessible.
Cons: Ropes. Mild danger. Extreme danger on 3rd peak. Just don’t.


  1. You will have heard of Stairway to Heaven, aka Haiku Stairs. I don’t advise it. The stairs have been heavily damaged by recent storms, and you’ll expose yourself to tresspassing charges and a fine. Not fun.
  2. The definitive guide to Oahu hiking is David Ball’s book, highly recommended.

The Hikers Guide to Oahu: Updated and Expanded (A Latitude 20 Book)

Experienced and novice hikers alike will benefit from the information in this updated and expanded edition of the best-selling The Hikers Guide to O’ahu. The author describes in detail 52 trails that will take you to O’ahu’s lush valleys, cascading waterfalls, windswept ridges, and remote seacoasts.

3. If you are a deeply experienced hiker and into extreme hiking, check out this site for (dangerous) adventures. (what I call “advanced” here, they call “easy” or “intermediate”. You have been warned.)


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