Jesse Middleton's avatar image.

VC at Flybridge. Co-founded WeWork Labs. Investor in 15 companies and counting.

My name is Jesse Middleton, I've run biz & product development, sales, IT & launched new markets for WeWork. Now I'm investing full time.

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  • How do you juggle everything and manage your time well?

    You do "biz dev, sales, IT, product development" and you're an investor? How do you manage all of these things efficiently without dropping the ball?

    Jesse Middleton's avatar image.

    The short answer is: Not always perfectly.

    The slightly longer answer is: It's a trial and error kind of thing. My roles within WeWork over the years have typically not been in parrael but in series. I ran business development followed by IT, product development, sales and finally M&A. Throughout that time (5.5 years) these overlapped very little.

    Investing is something newer for me. As of a couple of months ago I decided to go all in on investing full time. Before that it probably only took up about 10-15% of my time (my weeks typically consisted of 70-80 hours worth of work and meetings. The hardest part comes post-investment. Once you've agreed to put your money and time into someone else's dream, you have to really commit and support them for a long time. It's not always easy but I just try to prioritize and re-prioritize each and every day.

  • Is there a good way to avoid hiring the wrong people?

    Any warning signs without being too cautious and missing out on great potential entrepreneurs?

    Jesse Middleton's avatar image.

    There's an old mantra, "Hire slow. Fire fast." I tend to disagree. So does Mark Suster as he wrote a guest post in 2011 that still stands today (

    Hire fast. Fire fast.

    There's no sure fire way to avoid hiring "the wrong people." But you can correct it quickly if you're paying attention. Every organization has different values that they're looking for in their employees and these values can change over time. So the "perfect" candidate changes over time too.

    In the beginning startups are seeking people who are entrepreneurial, scrappy, do-it-all employees. The best team member is someone who can come in and roll up their sleeves writing copy, code and contracts. Over time, companies shift and begin to seek out experts instead. At this point jack-of-all trades are not as valuable.

    If you're an early stage company, it's most important to lay out not only the role and responsibilities but also the values you're looking for in a candidate. Once you have this you can at least make sure that the person is the right cultural fit at the time you hire them. This is the most important checkbox for an early hire.

    And if it turns out you're wrong just remember you can, and should, fire fast.

  • How many cities do you want to expand to within the next ten years?

    Hi. I love WeWork. I've visited your offices in SF as well as one in DC (not familiar with DC geography but I think I visited the one northwest of the White House). Anyways, I can see WeWork changing how office spaces are done in the future. Can you divulge on how ambitious WeWork's plans are? Do you plan to be in every major city in the world? Would that make economic sense?

    Jesse Middleton's avatar image.

    While we don't share our expansion plans publicly I can tell you that we've got some lofty goals. In addition to expansion to markets like China, Korea, Mexico, India, Hong Kong and Australia (, we're making sure we also focus on increasing the value of WeWork Commons (our digital platform - We have members from all over the world who have joined our member network and have found partners, investors, co-founders, employees and tons of service providers to help them start and build more successful businesses.

  • How often do startups get acquired because they 'failed?'

    There are countless stories of startup acquisitions in the media but I have heard that most startup acquisitions are because the startup failed to gain significant traction. As a result, the startup is selling their team (as opposed to their product). Is this true? If so, about what percentage of startup acquisitions fall into this category? And how does this even happen? Is it because the acquirer is friends with the founders or their VCs?

    Jesse Middleton's avatar image.

    Hi Mark,

    This is a great question and likely one without much data to go on when it comes to an answer. Most acquisitions withhold their acquisition details. This happens for a lot of reasons not the least of which is because it was an inconsequential deal to the acquirer. This doesn't, however, mean that the startup failed or that it wasn't a good deal for the founders/team that get to continue working together on something new and exciting.

    I don't believe that many startups are acquired because they are "friends" with the acquirer. I believe that most acquisitions happen because there's a good fit between the acquirer and the acquiree (this should be a real word). It's true that sometimes acquisitions happen because a startup failed to gain traction or momentum. But if the team is sharp, the product is good while the timing or luck (which accounts for 90%+ of early success) was off an acquisition can mean a new beginning for the startup. Often that new beginning lets the team continue chasing some or all of their mission while gaining some peace of mind with their acquirer's success.

    Mark Stanley's avatar image.

    Hi Jesse, Thank you for this answer and for clarifying things. I'm not familiar with how acquisitions work so this was insightful.

    Best of luck to WeWork X!