The Rise of The Solopreneur and Increasing Importance of Marketplaces

I believe that we’re moving towards a future dominated by ‘solopreneurs’ — individuals who work for themselves and have no intention of hiring staff or growing a team. I’d argue that recent shifts to a more fluid and mobile workforce are precursors to this future. No longer are workers joining a company with the plan of staying there for life; hell, I doubt many workers see themselves spending more than 5 years at the same company. This shifts the mindset of workers to be less aligned with their company and more aligned with their own future, which is a stepping-stone to working for yourself.

I believe these ‘solopreneurs’ will mostly be split into two categories:

  1. Those who are selling goods or services, e.g. Etsy/Shopify or Uber/TaskRabbit
  2. Those who are selling skills and knowledge, e.g. your traditional business consultants/contractors, which I believe will increasingly happen through marketplaces like HourlyNerd/oDesk

The Internet’s ability to provide business access to thousands of potential customers has made this future a possibility and we’re already in the nascent stages. However, as this paradigm shift continues to unfold, it will become more and more difficult for any one individual to break through the noise and acquire customers. It’s for this reason that I believe two-sided marketplaces will become increasingly important conduits for ‘solopreneur’ employment.

The symbiotic relationship between a marketplace and its supply makes for an ideal employment hub for ‘solopreneurs’. Marketplace companies are by definition reliant on their supply side, which makes it in their best interest to provide tools and support to be successful. That support comes in the way of: marketing, operational logistics, customer support assistance, community access, educational tools and much more. By providing a streamlined business framework, suppliers can more easily focus on growing their business. Additionally, marketplace network effects amplify the necessity of joining if there is a dominant operator in your space. Even if you’re able to build your business independently of a marketplace, the benefits (resources, more business, branding by association) of joining likely outweigh the costs.

While the Internet, existing marketplaces and a more fluid employment environment have laid the foundation for this transformation, I believe the larger catalyst will be the shift to remote work becoming the norm, which I believe is on the near term horizon. Once people begin to feel comfortable working from home and away from the traditional office, the leap to working for themselves will seem less daunting. As we continue to shift away from a labor based economy to a knowledge based economy, it will continue to make more sense for workers to move between jobs to increase their knowledge and leverage that into higher pay, or putting it another way — it will make more sense to become independent consultants or contractors.

This is why I’m so bullish on marketplaces and it’s a large part of what led me to CoachUp, and now 1stdibs. I believe we’re increasingly moving to an e-commerce landscape mostly dominated by HUGE winners, with a spattering of small-to-medium sized niche players. This has been the typical status quo for much of the post-industrial evolution world, however until recently I think you could make the argument the Internet was changing that. Unfortunately we’re reverting to the mean, as the majority of businesses have moved online and it’s now more difficult than ever to standout. Because of this, I believe these winners will often take the form of marketplaces, as they will best position to leverage the shifting workplace dynamics that increased ‘soloprenuerism’ will bring.


Three Big Announcements (Really 2 and 1 Minor 👍)

After nearly three and a half years at CoachUp, the time has come for my next adventure. It was an incredible ride and more than I could have ever hoped for in my first job, but I’m ready for a new challenge. That desire for something new was a big factor in another recent decision – moving to Brooklyn. That’s right, back-to-back bombshells; I am no longer with CoachUp, and Hillary and I have left Boston for NYC (only from a location standpoint, our allegiances are still firmly with Boston, the City of Champions).

CoachUp will always have a special place in my heart, and leaving was one of the more difficult things I’ve ever done. After Wesleyan my dream/goal was to join an early stage startup in order to learn how companies are founded and built. Joining CoachUp as the 5th employee afforded me that opportunity. I couldn’t have asked for a better company or group of founders to learn from and to embark on the rollercoaster ride that is an early stage startup with. I owe such a tremendous debt to Jordan, Arian and Gabe for taking a chance on me, despite my total lack of experience at the time and for teaching me what it takes to build a company.

I’m still not sure what’s next for me, as I don’t want to rush the process. A big part of what made the CoachUp experience so great was the amazing people and my passion for the vision, so I want to make sure the same can be said of my next role. What I do know is that I’m going to optimize for learning and that I want to stay in B2C or at the very least B2B2C. So If you know anyone awesome companies that are hiring in NYC/BK or anyone you think I should know, please shoot me an email grant (at) or tweet me @grantcov.

The 3rd announcement is relatively minor – I finally launched my food blog, Those of you that know me well, know that this has been in the works for sometime. With leaving CoachUp, I finally had time to get it up and going. The site is very rough and needs a lot more work, but wanted to get something live so I could start posting my recipes. Cooking has always been one of my largest creative outlets and favorite hobbies, so I’m incredibly excited to have a place to share that passion. So please go check out the site at and follow on Instagram, Facebook and Twitter (all @TheBellyBeckons).

Twitch is Still Just Getting Started

When I first started watching Twitch in 2010 it was still called and my friends thought I was crazy for watching video games instead of just playing them. The game I watched most was Starcraft 2 (still is) and rather than go directly to I would go to TeamLiquid (a Starcraft website) and check the “Live Now” section of the sidebar, which would list which pros were currently streaming. The most popular streamers were: Day[9], Huk, Idra, WhiteRa and Destiny. Each could sometimes draw up to 10k viewers under the right conditions, and when a big event like MLG would happen there could be as many as 35k viewers. Those numbers pale in comparison to what the top streamers and biggest events draw in today, but at the time they seemed massive. Despite the huge growth, I’m still incredibly bullish on the future of eSports (definitely not alone here) but also on Twitch as a whole. I believe the Twitch acquisition by Amazon will be as big as YouTube was for Google – maybe even bigger.

I still watch a lot of Twitch – but now instead of going to TeamLiquid or even to, I open the app on my phone. I’d say at this point 90% of my Twitch viewing is done on my phone. Back in 2010, I was still using a Blackberry, making mobile viewing impossible so all my stream views were on my laptop. When I got an iPhone 4s in late 2011, I still mostly used my laptop – I’m not sure if Twitch even had an app by that point, but if they did, I didn’t download it and the mobile web experience left a lot to be desired. More importantly, the iPhone 4s screen size made for a less than ideal viewing experience. So for the first few years out of college, I was largely reliant on laptop viewing, but with less free time I found myself watching fewer streams. Once I upgraded to an iPhone 6 last September the larger screen size was ideal for viewing, so I downloaded the Twitch app and boom – suddenly I’m watching as much eSports as I was in college (I already know how cool I am, so no need to tell me).

I have no doubt that the growth in screen sizes over the last few years has sent Twitch’s mobile views skyrocketing. Fortunately, for them the core UI for choosing a stream – looking to see if anyone you follow is online, browsing by game or popular streamer – also lends itself incredibly well to mobile viewing due to its simplicity. In fact, I much prefer the mobile app to the desktop experience because it cuts out all the bullshit and is just so simple. That simplicity is part of why I think it’s a far better mobile experience than YouTube, where more action is required to curate streams (?) and watch for longer stretches. The frictionless ability of firing up a stream lends itself to sporadic viewing, which is ideal for a mobile world. There are also far fewer ads on Twitch as compared to YouTube, and let’s be honest, ads are the absolute worst and people are now more sensitive to them than ever. Obviously there are ad blockers, but most people don’t use these on mobile, and they don’t work in native apps (at least to my knowledge) so extended YouTube viewing can get very frustrating.

Although eSports and gaming are Twitch’s bread and butter, other genres have been recently gaining steam. The recent ‘official’ launch of Twitch Creative and simultaneous streaming of Bob Ross was absolutely massive. Since then, the ‘Creative’ category has been consistently in the top 20 for viewers and Bob Ross Monday’s continue to draw huge crowds. Gaming Talk Shows are becoming increasingly popular – that category consistently places in the top 20 as well. Other atypical genres have been gaining momentum too: Poker, Game Development, D&D, Board Games and Music have all seen huge growth over the last year?. One of the most interesting aspects of many of these growing categories are that they’re often offline events being streamed. Twitch is no longer just for streaming things from your computer, but for streaming anything. Then there is the Twitch Plays phenomenon that begin with Pokemon, whereby the Twitch chat controls the game. I could go on, but the point is the sheer number of games and categories with live streamers is staggering – and everyday it seems people are finding new things to stream and new ways to leverage the Twitch network.

YouTube’s fear of losing eSports and streaming to Twitch has become increasingly obvious, evident by their recently launched competitor: YouTube Gaming. Unfortunately, I think it’s too little too late and they will be unable to catch up to Twitch, which has built an impressive moat via network effects (just checked YT Gaming and the current top stream only has ~1k viewers). Periscope and YouNow are their only real competitor, and I think they’re both for a far different use case – one that Twitch is willing to concede. Ustream, while once relevant, is mostly an afterthought at this point and while hitbox has gained some users, they’re still far behind. In short, it appears that Twitch has already won in what I believe to be a mostly winner take all market.

Twitch is exploding because streaming is exploding, and they’ve clearly cemented themselves as the leader in the space for every category. The massive growth expected in eSports over the coming years will no doubt be Twitch’s primary growth engine, but I believe these atypical categories will play an increasingly large role in their future as well. For example, recently drone racing videos have been reaching the top of Reddit, and I’d venture a guess that within the next 1-2 years we will see that as a top 20 category on Twitch. There is no doubt in my mind that streaming as an entertainment vehicle will continue to grow across the board and if you’re serious about streaming you would be foolish to choose to build your audience anywhere other than on Twitch.

Small Changes Can Have a Big Effect

It’s important that every product team have a North Star – the ultimate vision and goal for what you hope to achieve with your product. Every decision should be weighed against whether or not it aligns with and helps the team reach said North Star. Unfortunately, this can often lead to enormous undertakings in the hopes of reaching our final destination as quickly as possible. When instead, we’d often be better suited to make small incremental changes that in aggregate can have a massive effect.

When trying to establish a new personal habit, the common advice is to start small and build a foundation. Focus on lots of little wins in order to build a positive feedback loop. If after multiple attempts you’re unable to positively enact change, only then does it make sense to make drastic changes. The same advice holds true for product development. Figure out what your product currently does well, or what your foundation is, and then begin mapping out small quick wins to build on your success and keep you headed in the direction of your North Star.

It can be very tempting to build an amazing new feature – the one that you just know in your heart of hearts is going to change the trajectory of the business. During my time at CoachUp (prior to my move into a fulltime product role) we had a few instances where people were convinced that a certain feature was all we needed to 10x the business. Unfortunately, nothing that we’ve built has had that effect. This is not to say that these ‘business changers’ were all failures; some did move the needle in the right direction and they were all learning experiences – but we didn’t suddenly start printing money once they went live.

Instead, we had the most success when we focused on smaller wins that improved the core CoachUp experience; e.g. finding, booking and training with a coach. This aligns with our North Star of making it easy and accessible for anyone to train with a private coach and increase their athletic confidence. These small wins add up – one particular success was when we improved the response time of our coaches to client inquiries by over 50% without making any huge changes or launching any new features. By making small tweaks over several weeks, we were able to move our KPIs up and to the right drastically. Now this is not to say that we didn’t build large new features or that you should avoid building large new features entirely, but rather it’s important to do so for the right reasons and that you have an iterative approach for implementation, allowing you to learn and adjust accordingly.

The large scale attempts to launch a completely new product or to try something that deviates from what has worked previously can come later, once the company is more of a scaleup and less of a startup. At that point, you’ll have the luxury to take moonshots, without sacrificing survivability – in the earlier days though, you don’t have the resources to afford whiffing on a large development investment. The only time it might make sense is if small improvements aren’t enough to get you to your next round of funding, and a Hail Mary is your only option.

A hockey stick style growth curve, when zoomed in on any particular area doesn’t look like much, but sustained improvement over time can add up to a whole lot. Just like Rome wasn’t built in a day, neither will you achieve your full product vision overnight. But if you keep iterating, improving and learning you might get there eventually – just remember there are no shortcuts and ‘overnight’ successes are rarely, if ever, the reality.

Unplug to Recharge

Have you ever written an email that began with “sorry for the delay,” when replying in less than 24 hours — how about 12 hours, 6 hours, 3 hours? I know I have. Hell I’ve responded to emails in less than an hour and apologized for the delay when it was a conversational, back-and-forth thread. The unfortunate reality is that since the advent of email, and more specifically smartphones, the expectation is that you’re available and reachable 24/7. It’s for that very reason that it’s more important than ever to unplug and disconnect on a regular basis.

Work fatigue and burnout are very real and it affects all of us in different ways; you often don’t even realize you’re suffering from burnout until you’re able to get away for a few days. You’ll be amazed at how refreshed and re-energized you’ll feel when you come back to work after time off the grid. I’ve found that the weekend is not quite enough time to get everything out of your system, so ideally extend it with a Friday or Monday off. It’s remarkable how much longer a 3-day weekend feels as compared to a typical weekend – certainly more than the 50% longer simple arithmetic tells us.

Every June for the past few years, my dad, brother and I take a four-day trip where we completely unplug. It’s a great opportunity for us to catch up and be present in the moment. And for my brother and myself, who both work at startups, it’s a great opportunity to take a much needed technology timeout (my dad is mostly retired so he’s always recharged J). Plus, I always feel that the following week at work is one of my most productive of the year. Email, social media, Reddit, etc. all have serious habit forming loops, and if you’re able to break free from them for a few days, it can help reset your equilibrium. That first week back, I feel I’m far more focused on what’s actually important and better able to block out the noise (email, damn you!) we all deal with on a day-to-day basis.

When you work at a startup, going completely incommunicado can seem scary and downright impossible, but it’s not. Take a deep breath and remember that (until very recently) it was the norm to be difficult to reach when outside of the office. The most important thing will be communication with your team — you need to let them know well in advance that you won’t be reachable. That means you need to make sure all of your work is in order and that you won’t be the blocker for anyone else’s work. I’d also advise against disconnecting right before or after a big project (and obviously not right in the middle of one either!), because not only will you likely need to be available but you’ll just end up stressing about the status of said project.

I know it’s hard to pump the brakes in the fast paced, always “hustling” and “grinding” world that we live in, but think of it as an investment. Because if taking complete ownership of a few days will help you come back to work with renewed focus (and believe me it will) then it’s well worth it, for you and your company. It will be tempting to check you phone occasionally, but do your best to resist the urge. If you do feel that checking in will help you manage your stress levels, go ahead, but only get involved or respond to something if it appears absolutely mission critical — anything else can wait until you’re back.

Give it a try this weekend: Friday after work, turn off your laptop, phone and any other device that you get email from and keep them off until Sunday night, or if you’re feeling particularly daring, wait until you’re back at work on Monday. I think you’ll feel particularly ready to kick some serious ass at work; hell you might even be able to skip the morning coffee.