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There are ways to optimize your contributions by transferring smaller amounts each year and waiting for your tax rate to reset. But I usually just go with the brute force method.
Well you have not really specified how close or far you were from getting it or if you even tried yet so far.
General rule of thumb, get a marketer and sales exec early. User marketer for reports ASAP. Develop the perfect targeted banner ad (usually has 60+% conversion yield) and invest aggressively into it while also dumping everything you have into the support teams to keep the site growth in parallel with the user base growth. Don't be afraid to take loans this early on as rapid investment in the right places pays off quickly.
If the site outpaces you sell it and use the proceeds to solve the problem that caused you to flip the site and repeat.
If you do this properly your biggest problem should be controlling the insanely rapid growth of your site and how your server is literally under constant threat of a crash due to rapid growth. keep doing 1 day ad contracts constantly and keep the filters filtering a little bit above what your current user base is as you will catch that limit by the time the contract is ready and open. I think that summarizes the overarching strategy.