having worked at grubhub and spent a fair amount of time in discussion with ceo/founder matt maloney: - the leadership during the peak of competition for minds

having worked at grubhub and spent a fair amount of time in discussion with ceo/founder matt maloney: - the leadership during the peak of competition for mindshare in the space was exceptionally weak and overconfident. the grubhub/seamless merger led to a completely split company culture between NY and chicago. - when they were on top, they were a shitty company with scummy practices (even for the space) that made restaurants very skeptical of them specifically. grubhub effectively ran like a protection racket. they bought up tons of "menu pages" websites and restaurant listing sites and launched fake websites to overtake the online presence of grubhub restaurants (including replacing their phone numbers in google summaries with voip numbers, calls through which restaurants were billed an "order origination" premium for.) they broadly resisted the desire of their restaurants to share ownership of their customers (or even be able to determine who their customers were.) - they completely lacked the ability to plan long-term or even guess the consequences of any action they would take and would do things like "suddenly, without warning restaurants, offer a 50% off deal on lunch all across new york city," leading to huge numbers of canceled and delayed orders and further eroding their public perception. - they were already public by the time that uber eats, doordash, and postmates were really aggressively entering the food delivery space and thus had to grow and ship with realistic constraints instead of burning investor money to disrupt in hopes that they would be profitable. probably a million more reasons beyond that, but just off the top of my head a few ways the ball was dropped/the deck was stacked against them.