What's the most common mistake second-time entrepreneurs make? originally appeared on Quora: the place to gain and share knowledge, empowering people to learn from others and better understand the world.
What's the most common mistake second-time entrepreneurs make?
Picking the Wrong Market
Many second-time entrepreneurs who were successful the first time end up picking the wrong market the second time. Instead of using their unique background to go after a market they have a unique advantage in, they branch out to an area where they would be more socially acceptable in broader society.
Countless second-time Internet entrepreneurs I know end up starting sustainable restaurants, private jet companies, wineries, clean energy, or other things where they (1) do not have a proprietary advantage; and (2) in an area that lots of other people are starting companies in.
Entrepreneurs that have done it right are people like Brian O'Kelley who had a great success with Right Media and then followed it up with started AppNexus, a company in the same industry where Brian could use his unique knowledge to his advantage.
Great entrepreneurs start companies with the Venn diagram intersection of (1) will be very valuable in the future; (2) most people do not think it will be very valuable in the future, and (3) an area the founders have an advantage in.
A few other things second-time entrepreneurs do wrong:
Over-Fitting Decisions From Your First Experience
Each new company is different, and as times and industries change, so should strategies and tactics.
If your first company was a success, you are at risk of copying too much. You might not clearly understand what went right and what needs to change. You also might not appreciate market changes (for instance, a good recruiting strategy in your first company might actually now be a bad strategy).
If your first company was not successful, you might try to pendulum too much in the other direction.
Hindsight gives us very selective memory. You may forget all the bad hires you made in your first company or you may forget how hard it was to get your first five clients.
Alternatively, if you had a bad experience with a venture capitalist, you could be at risk of generalizing this experience to all VCs.
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