The Entrepreneurs Rollercoaster

by Jason -- November 3, 2011

I’m currently sitting on a plane back to Korea. After almost 4 weeks in the states I’m excited to sleep in my own bed, cook my own food, get back to my routine and wake up next to my wife.

It has been a roller coaster of emotions the last few weeks. Now more than ever the realities of trying to start my own business have been hitting me, and to be perfectly honest, it’s been difficult. In this post I’ll share the roller coaster that I’ve been on the past month.

Quick Background

I started over a year ago. We’re a marketplace of self-guided tour itineraries that are written by local experts. We give travelers the information to be their own tour guide.

The Highs of Being an Entrepreneur

I’ll start this off with 2 pieces of exciting news.

1 — Unanchor just had its best month yet! We’ve been hovering around 2 sales per weeks for the last few months. In October we jumped to over 5 sales per week – almost 1 per day. It was very exciting.

2 — My co-founder Mohammad has been heads down the past 3 months on a brand new back-end system. We’re finally getting ready to move away from our Microsoft Word/PDF system and soon, itinerary writers will create their itineraries on our website. This is exciting because once this in place we’ll be able to do a lot of interesting things. For example – give the first day away for free, create a mobile app, take segments from one itinerary and mash them with other itineraries. Currently, none of this is possible, so this is the beginning of a really big step forward for us technology-wise.

The Lows of Being an Entrepreneur

The primary reason I was in the states was for 3 weddings. While there, I took advantage and met with as many people as possible. I was able to meet and talk with entrepreneurs, angel investors, and VC’s; many of whom were involved with the travel industry and could share their first-hand experiences.

In fact, I was able to talk with travel entrepreneurs who had previously tried many of the things that Mohammad and I have discussed for growing and scaling our business. Overall, the conversations were generally negative. Many of the conversations subtly and not so subtlety hinted to the fact that our ideas would be extremely difficult to implement and that we might be better off trying something else.

Here were my main takeaways from the meetings:

  • Competition is fierce in the travel-planning industry.
  • There’s a lot of free content out there.
  • We need to sell a LOT of $5 itineraries to be a profitable company.

Finally, on Monday we found out that we did not get in to Y-Combinator. For those unfamiliar – Y-Combinator is an extremely competitive program that invests money into web startups and helps them accelerate their growth by providing guidance, mentorship and introductions. To be honest though, I’m not too disappointed about not getting in. I knew the chances were extremely slim as the program is harder to get into than Harvard. I had to hope for the best and getting bad news is never enjoyable, but it’s not something we’ll get stuck on.

What’s Next?

So, to say the least it was an interesting October. In the end, we’re certainly not giving up yet. I know there’s a lot of value in the self-guided tour itineraries that we’re enabling people to create and sell.

In the same respect though, we can’t go after this problem forever.

In light of the things I learned, Mohammad and I are going to discuss our business and product priorities again. We’re going to try to figure out what things we can test sooner rather than later. All, I’m sure, to be discussed in future posts.

Be awesome and help us share:

9 Responses to “The Entrepreneurs Rollercoaster”

  1. awesome post! I love your determination. The travel industry is a big market. As long as you stay focused on making money and stick with it you will be successful.

  2. Thanks Rishi! I really appreciate your support as well.

  3. Keep at it. All great businesses start somewhere. Stay focused, passionate, make smart decisions and good things will fall into place. I suggest reading The Purple Cow for some inspiration. Even though competition is heavy in the travel industry, as long as you’re providing good value to customers and can communicate that value, they will come.

    Another thing… Bay Area represent!

  4. Thanks for the comment and advice Gerard, I really appreciate it. We’re keeping at it.

    Good luck on your trip as well! I checked out your site and it looks really exciting :-).


  5. Thanks. Looks like we’ll be hitting up many of the places you went on during your career break. Should be good times I hope.

  6. Yeah, I noticed that as well. Good choice in destinations! Hopefully we’re still in South Korea when you guys make it here. And I’m sure it will be amazing.

  7. I’ll be sure to ping you when we get close there!

  8. Hi Jason.
    Great site and I like what you are trying to do. Your man after my own heart. I traveled myself for nearly 20 years, few of those spent on a Kibbutz in Israel. now back home a much much older man, after finally settling down in Thailand as an English Teacher. Loved it. So back home in Nottingham and started a TEFL Business. hit me up with an email and you might be able to make some cash out of my site.
    No matter what keep on pushing you’ll make it in the end. Sean

  9. Hey Sean — Thanks very much for the comment and checking out our site! Sounds like you’ve had a pretty awesome adventure. I’ll send you an email. Thanks again! Jason

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