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 Unanchor.com 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.

Filed under: Unanchor