Stuart MacDonaldEntrepreneur | Marketer | Advisor | Father
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Advisor | Previously CMO FreshBooks.com, CMO Expedia.com & founder Expedia.ca, co-founder mesh conference. I help with business growth, strategy, marketing and leadership. Mentor, Investor, Board Member and passionate about your success. When can we talk?


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It's going to be really tough to go from Newbie to Trusted Advisor in one go. You might be able to hustle yourself into something but I'd focus on developing yourself. Why not go to work for an established consulting firm if that's truly where you want to apply yourself? You start to see inside companies and build more skills. You also build your credentials which will help in the future.

If none of that appeals, maybe a role at a not-for-profit, who typically would give you more leeway in your role and maybe speed things up in terms of development.

But - not the answer you want to hear, I bet - consultants get asked to help teams and companies because they are experts at what they do, typically having developed those skills with a lot of training and time.

If you don't want to do the work to develop yourself into that type of Trusted Advisor, I'd ask you to ask yourself why you're going down this path?


As former CMO of Expedia I can tell you that being focused will trump any theoretical upside of having different names. To this day there's a struggle to build daylight in meaning between Hotels.com and Expedia's core hotel business - and there have literally been billions spent on trying to do that over the years. Get clear on who you're for, the problem you solve, what insight you are building against and your positioning against that. There's enough work there on its' own - believe me. Good luck.


That's a much more complicated question than it appears to be, as there are multiple sources which will get you some of the inventory, but nothing which will get you all of the inventory. If you look at an OTA, they are pulling from typical sources like SABRE or Amadeus, but also from what is in effect their own inventory, where hotels are either going in via an extranet or there's some kind of direct-connect to the system the hotel is operating on (which could be one of many, including none at all). In fact, some of the OTA's make that proprietary inventory available too, via an API and on a commissionable sales basis. There's just no one-size-fits-all access point - especially when you consider that worldwide the hotel business is actually very un-aggregated with something like 80% of all hotel room capacity operated independently (that is to say, not branded or part of a chain like Starwood, Accor, IHG etc.). It's a big part of why OTA's have invested so heavily in technology to manage and distribute this type of inventory. It's not easily done as the technology used in the hospitality industry is often not great and it's unconsolidated to there's value and negotiating strength to be brought from consolidating it.


That's a huge question - but in my view it really boils down to four things:
1) A clear sense of the problem they were trying to solve;
2) Crystal clear focus on only the most high-impact things;
3) Relentless pursuit of excellence in execution.
4) Luck.

That fourth one mightn't be a popular one to state, but the truth is that there are a lot of companies who try to do 1 through 3, but 4 always comes into play and Google is no different.



Let them find you. The more you demonstrate through what you do and how you do it that solving a problem specifically for them, the easier it is for them to find you and recognize that you are a good alternative for them to consider. It's all about being deliberate and doing all you can to reflect back to them that you get them and their problem.


You avoid it. How? By having a clear plan and having decided ahead of time what's important. Many entrepreneurs, especially those without a lot of experience at it, confuse hyper-activity with progress. Don't do that. Drive your own activities, gauge each thing you do against it's impact on making the future you want happen - and most importantly, say No a lot. Stay focused on impact and remember that all urgent things aren't actually important things.


It really depends on what you're looking to offer, but generally you should allow people to try before they buy, encourage and help them while they try it out and then ask for the business.


You're likely out of luck. If you think that it really was an oversight, have an adult conversation with the people and see if there's some kind of mutually beneficial resolution possible, recognizing that back-dating shouldn't be done. Perhaps there's some kind of adjustment to be made to the amount of equity you get today or something along those lines.



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