Spend too slowly in a changing market. And throw good money after last year's ideas. Much requires instinct, not logic. If you're waiting for the perfect time, it will never happen. Also, learning how to create a culture in your company.
Word of mouth is the best way.
Don't grow too fast and displace some of the people who emotionally helped build the firm. Turns out the guy attends Herring events regularly, including their gig in London. I also met the new CFO of Red Herring, Doug Jeffries, who'd just relocated from San Diego, and wished him well. Longtime publishing guy, with a lot to say. They weren't kidding.