Featured Article

A Silver Bullet for Travel Planning [Part 2 of 4]


8 minute read


Travel planning consists of two big pieces. Searching for relevant information and creating an itinerary from what you find.
In the first of this four part series we talked about problems associated with search.
In this second part we’ll address what we believe the solution to this search problem is.
Parts 3 and 4, will likewise address the problems & solutions related to creating itineraries.

Everything you’ve been led to believe about what “travel search” means is wrong. PlanitWide is the first and only genuine travel search solution that doesn’t need you to know how to search and helps you find  ANYTHING travel related for ANYWHERE in the world. At the same time, it provides results that are far more useful and relevant than traditional search engines

It accomplishes this by:
1. Upending traditional search by doing away with the need to think of travel keywords
2. Offering fewer, targeted results
3. Providing a more useful result display and higher quality results
4. Enabling granular personalization of results
5. Providing results across all formats: websites, books and apps

Traveler Type: All travelers

Summarizing Part 1, we said that finding travel information is an inefficient and stressful experience because of:
1. The complicated makeup of the travel space
A sea of disconnected travel providers
The role of mental overload & habits

We also said that:
a. Search is at the heart of easier travel planning and is currently sub-standard
b. Only a holistic solution that provides for, and makes it easy to manage all the interrelated pieces, will make travel planning better

So picking up where we left off, its clear that for ANY travel planning solution to be truly effective it must offer travel search that encompasses the 1000 + interrelated factors in the travel space.
But that raises an important question…

What is Travel Search?
 [Continue Reading...]

A Silver Bullet for Travel Planning [Part 1 of 4]


Thanks to Jerome Shaw (Owner/Editor, TravelBoldly) and Nathaniel Boyle (Founder/Host, DailyTravel Podcast) for their time and invaluable feedback on this post prior to publishing it.

8 minute read

Travel planning consists of two big pieces: Searching for relevant information and creating an itinerary from what you find.
In this first of a four part series we’ll talk about problems associated with search.
Part 2 will address what we believe the solution to the search problem is.
Parts 3 and 4, will similarly address the problems & solutions related to creating itineraries.

There are three reasons why finding travel information is such an inefficient and stressful experience:

  1. The complicated makeup of the travel space: Any of 1000+ factors, many interlinked, may need consideration.
  2. A sea of disconnected travel providers:  No easy way to figure out who has the best information for any kind of trip
  3. The role of mental overload & habits: Our finite mental capacity can’t cope with the complexity of planning travel.

The result is often sub-optimal trips, or worse, not traveling at all to avoid the pain of finding information.

Traveler Type: All travelers


“Travel planning stinks! A lot!”
“Why can’t trip planning be less complicated?”
“Is this the best itinerary I could come up with?”
“Am I missing out on something cool?”
“Have I forgotten (to plan for) something?”

We’ve felt or heard these sentiments over and over again from friends, family and others.
New and old providers inundate the travel space promising all kinds of solutions. Yet, nothing seems to be improving. If anything, travel planning is getting more overwhelming with each passing day.
Why is that? And what will it take to make a difference? What will it take to create the best possible itinerary for every trip within hours instead of weeks? Or without having to pay a “boutique” agent an arm and a leg?

We believe the answer is PlanitWide.
But before we discuss any solution, let’s first look at what ails travel planning.
 [Continue Reading...]

2 Hugely Important Thought Starters For First-Time Entrepreneurs From Startup School NYC

startup_school5 minute read

Attending Startup School triggered two hugely important thought-starters for me which could be vital to the success of PlanitWide and many other startups:
i) Embed persistence and resilience into your startup’s culture because you are probably going to face a lot of rejection and resistance throughout your journey
ii) Should applying to Y Combinator be a first resort instead of a last resort?

Applies to: First time entrepreneurs

Y Combinator (YC) held its first ever Startup School in NYC on June 18th, 2014. Given YC’s stature in the startup community and the quality of speakers at past Startup School events held in the valley combined with the fact that I’m based in NYC, this was too good an opportunity to pass up. So I applied on behalf of PlanitWide and was fortunate to be invited to attend the event.
It had Alexis Ohanian as its MC and an awesome lineup of speakers:

In addition to the above, there was also a 25 minute YC Office Hours segment where YC partners, Sam Altman and Garry Tan asked questions and offered advice to three startups who were part of the audience.
As you would imagine, every session was engaging and full of practical tips and advice. The highlights of each session are here (hat tip: Jason Shen) and the full video of each session is here. I definitely recommend viewing both.

So what is this post about?
 [Continue Reading...]

OnTheRoadIn.Com’s Road Log Is Better Than Google Maps When It Comes To Mapping a Road Trip Through Baja California

Let the ups and downs begin6 minute read

‘s Road Log is the most comprehensive guide I’ve found on mapping a road trip through Baja, California.
It contains:
a) Distance Charts
b) Information on immigration and non-immigration documentation
c) Pictures & a listing of highway signs, all translated into English, and
d) The most detailed road log that includes mile markers, landmarks etc to ensure you never lose your bearings

Not only will you not find detailed information like this anywhere else, the $12.99 you invest in it will save you hours you’d have otherwise spent trying to:
i) (unsuccessfully) find such information, and
ii) put together a realistic plan for every day of your road trip

Applies to: All travelers

Planning a road trip takes significantly more effort that most other trips. This is simply because you are now directly responsible for getting from Point A to Point B. In that situation, a host of variables need consideration that otherwise wouldn’t, like the kind of vehicle you’re going to drive, fuel efficiency etc. I think it’s safe to say that that you can add a few more variables in the mix when planning a road trip through Baja California, like it not being advisable to drive at night, for example, or there not being cell phone signal for long stretches of road. Fortunately, OnTheRoadIn exists to make mapping this road trip a breeze.
 [Continue Reading...]

ProductCamp Boston: How Speaking At Local Entrepreneur Events Can Help Find Early Adopters For Your Startup

Pcamp6 min read                                                                                                                                     

Learnings from this experience:
i. When applying to speak at ProductCamp, always apply to lead multiple sessions on more than one topic
ii. Small events like ProductCamp are opportunities to leverage and re-purpose past efforts
. Some of  your early adopters may be in the audience. Take advantage of your session leader position to talk more about your offering

1. Applying to Lead Sessions:
ProductCamp is unlike most startup conferences. Anyone who thinks they can add value to the audience of this event can propose to speak. Speakers are then chosen based on votes by people attending the event. The number of votes determines how big a room you get.

I’d attended ProductCamp Boston a couple years ago and my biggest learning from that event was that I needed to be a speaker at as many events as possible. While I’m admittedly an applause junkie, I realized that public speaking is a great way to expose a startup’s brand. In the case of ProductCamp, that exposure is to very savvy members of the local tech community. I applied to run two sessions:

  • A workshop on Lean Six Sigma techniques to help narrow the focus
  • A live demo on how to use Trello to manage to-do’s, meetings etc

To my surprise, I got enough votes for both sessions to be accepted as part of the schedule. This meant that of the four 50 minute slots (each with multiple talks), I’d be talking for half that time!

Lesson #1: When applying to speak at ProductCamp, always apply to lead multiple sessions on more than one topic. If I could think of two things that could help other entrepreneurs & product managers, you can too.

2. Preparation:
Thanks to all the work we’d done preparing for the Office Optional conference, we didn’t have to scramble to setup anything. All we did this time was:
a) make a copy of the Office Optional landing page with links to templates our Trello boards
b) change the name of the event on it and
c) gave it a URL referencing ProductCamp

Lesson #2: Small events like ProductCamp are opportunities to leverage and re-purpose past efforts.

 [Continue Reading...]

2 Reasons Why DisabledTravelers.com Is A Must Visit Resource For Disability Related Travel Planning Within And From The USA

disabled5 minute read

DisabledTravelers.com is a one stop shop for disability related travel planning advice within and from the USA. Content on the site is particularly useful and relevant because it is owned and operated by Jeremy Rynders, who has first-hand knowledge of the special needs of disabled travelers.

Traveler Type: Disabled travelers

If you are someone who has had to search for information on traveling with a disability within or from the USA, you’d know that for the most part, information is scant and available in bits and pieces across the web. Unless of course you’ve come across the DisabledTravelers website, owned and operated by Jeremy Rynders.

Here are two reasons why DisabledTravelers is a must visit resource for disability related travel planning advice within and from the US:

 [Continue Reading...]

Attending the Office Optional Conference Part 3: Learnings From And After The Event

OO-AA-presenting10 Minute read                                                                                                                         Photo Credit: @sodiumhalogen

There’s a lot more to becoming a great remote team that meets the eye.
b) There are ways to becoming the unofficial information curator of any event which could give you great exposure.
c) Consider the match between pages you want to direct an event audience to and how that maps to their interests.
d) Small mistakes in analytics setup can give you nonsensical data that you’ll have to waste time figuring out.

Target Audience: Inexperienced entrepreneurs considering adding public speaking to their marketing strategy.

In this 3 part post, I’ve been sharing our experience of applying to speak at the Office Optional conference & what we did to prepare for it (Part 1), issues we ran into and how we worked around them (Part 2) and finally what we learned from it all (this post).

I think the learnings fall into three buckets:
i) What we learned from the event about remote working
ii) What else I could’ve  done while I was at the conference
iii) What the traffic to our landing page and the dedicated conference page showed us

i) What I learned from the event about remote working
Attending this event was even more eye opening that I’d envisioned. I had familiarized myself with the topics that were going to be covered. But nothing could’ve prepared me for the stream of high quality expertise that flowed through the each of the talks.
I’m happy to say that I received very encouraging feedback on my talk as well.

Tool Talk: Trello from LeanStartupConf

Admittedly, many of the talks referenced topics that would become relevant to PlanitWide if we survived long enough to grow, but the central message of doing more to connect with your team members was unmistakable.

It’s very easy to get caught up in assuming that just because you may not need a specific kind of interaction or need to connect at specific intervals, that others in your team wouldn’t need it as well.
And just to give you a sense of this, see this sampling of tweets sent out during the conference (#OfficeOptional):

 [Continue Reading...]

3 Reasons Why TravelFashionGirl Is A Must Visit Travel Planning Resource For Any Woman

black-24481_64010 minute read

If you are a woman looking for advice on what to pack depending on where you are going as well as tips on how to pack and how to stay beautiful during your travels, Travelfashiongirl.com should be your go-to travel resource.

Traveler Type: Women 

Yes, I know. I’m a guy writing a post about a resource focused on women. But I know a great resource when I see one (even if it doesn’t apply to me) and in my view, TravelFashionGirl (TFG) is as good as they come. Here are three reasons why:

1. Ingenious, blended focus on packing and fashion
Instead of giving advice on packing and fashion as if they were discreet considerations unrelated to each other, TFG combines them ingeniously by providing advice in the form of packing lists that are tailored to and sorted by destinations as seen below:

tfg-packing lists

Each destination section above consists of a series of posts that either consist of packing lists for a specific country/city or they guide you on what to wear in a specific country/city. See the example screenshot below:

 [Continue Reading...]

Attending the Office Optional Conference Part 2: Issues We Ran Into Preparing For The Event & How We Worked Around Them

Frustrated_man_at_a_desk6 Minute read

The smallest thing that can go wrong, will go wrong especially when you’re strapped for time. Start preparing earlier than you think you need to.

Target Audience: Inexperienced entrepreneurs considering adding public speaking to their marketing strategy.

In this 3 part post, I’ll share our experience of applying to speak at the Office Optional conference & what we did to prepare for it (Part 1), issues we ran into and how we worked around them (this post) and finally what we learned from it all (Part 3).

As I mentioned in Part 1, prior to the conference, our plan was to have the following in place:

a) a landing page to capture email addresses
b) a survey form that people submitting email addresses would be led to
c) a final thank you page that people completing the survey would be led to, with links to this blog & social media presence
d) a list within Mailchimp set up to receive email addresses submitted
e) populated the blog with a few posts
f) a dedicated web page just for the conference from where attendees could copy templates of Trello boards I’d be discussing in my talk (along with links to the blog and landing page)
g) Google Analytics (GA) installed on all site pages to measure traffic. Within GA, goals set up to measure how many people reached the final thank you page along with what path they took to get there)

The two biggest issues we ran into were:
i) the design of the landing page to capture email addresses
ii)populating the blog with a few posts

 [Continue Reading...]

2 Big Reasons Why offMetro Is Way Better Than The First Page Of Google For Planning Short Getaways From San Francisco – Part 2: Quality And Relevance Of Information

san-francisco-143983_64010 minute read

offMetro trumps the first page of Google comprehensively when it comes to planning short getaways from San Francisco.
The quantity (Part 1) & quality of information it provides is greater & better than every other resource presented in those search results.

Applies to: All traveler types

In this two part post Ive been comparing offMetro versus the results that appear on the first page of Google across the critical dimensions that matter:

  • Part 1 – The quantity of information
  • Part 2 – The quality & relevance of information

Part 2 : Quality & Relevance of Information

A. Google:
As I showed in Part 1, here’s what the results on the first page of Google look like if you did a search for “weekend getaways from San Francisco” (click on image to enlarge):


This time, I analysed these results for how they performed in terms of quality and relevance. The analyses and observations for each of these results are summarized in the table below.

All the site names link to the search results as shown in the screenshot above.

[Continue Reading...]