business startups

Slack vs. Teams

The most important tool in a company’s arsenal is communication. Companies that are effective at communication are able to get things done quickly and efficiently. Now that everyone is working remote, having great tools to be productive is more important than ever.

I’m sure you’re busy so this isn’t going to be an in-depth review of every feature but if you’re looking at Slack vs. Teams then I’ll talk through the pros and cons of each product and how you should pick the best product for your company. I’ve used both Slack and Teams for multiple years and while each has strengths each also has weaknesses.

Communication tools reflect the culture of the company and the way the culture and leaders of the company choose to communicate. If your culture is broken, or your company is dysfunctional, tools aren’t likely to fix it. Also if the leadership of an organization doesn’t lean-in, the tools will be less impactful and there are tons of examples of either Slack or Teams being rolled out and not really embraced by the executives of the organization.

If you’re going to take the dive into these tools, really try to get the commitment of all-senior-leadership to try to use these tools in favor of long email chains and countless meetings. This time in history is unique because remote work cultures are really well suited for these types of tools. Organizations that take the plundge now should commit to the tool for at least a few months to really understand the organic benefits.

If you’re new to these tools, it’s important to understand how they may be different from your existing communication tools.

  • Like SMS, it can be a real-time conversation or you can respond to message and questions asynchronously 
  • Unlike SMS, it’s oriented around topics/groups
    (and you can easily leave or silence a topic/group)
  • Unlike Email, group conversations are automatically persisted so new people can get the benefit of past discussions and decisions.
  • Lastly… conversational groups are best when they can be created and disbanded organically by the organization itself. This is bottom up communication, not IT led communication.
Five minute feature overview of Slack and Teams


While Slack was a leader in this space, it wasn’t the first chat based collaboration tool. Campfire, IRC and HipChat have been around for years before it. What made Slack successful was their timing and freemium model that appealed to early stage startups.

The freemium model allows anyone to setup a slack for their company for no cost and gets an initial Slack experience that works with all the bells and whistles while keeping a history of up to 10,000 messages. This led to rapid growth of Slack and a lot of adoption from early stage startups.

Microsoft Teams on the other hand is part of the Microsoft Office suite, so while it’s not free, it’s often perceived as free because it’s included as part of the Microsoft 365 Business suite.

The basic paid version of Slack is $6.67/user/month and the paid version of Microsoft Basic Business is $5/user/month.


If your organization is using the Microsoft tools already, including Sharepoint, Outlook and Skype for business meeting infrastructure then Teams is really compelling both from a configuration standpoint and a cost perspective. There’s less external dependancies and you’ll get the majority of the benefits. In general I feel that many of Microsofts tools are good enough. I do hesitate to call them great and the shortcoming is from many layers of software that try to tie together but don’t always… Two example…

  • Teams lets you schedule a meeting but it’s settings are different from how you schedule it in Outlook or how you schedule it in Outlook on the Web. So there’s three ways to schedule a meeting and if you do it wrong, your conference system may not work right.
  • Another area I found confusing was that while Teams was integrated into Microsoft Office it was often confusing where to find key files. Is it in the Team folder, The personal OneDrive, the Sharepoint folder or did someone forget and email it and it’s stuck in Outlook as an attachment?

While there’s certainly room for improvement, I do think that the File Folder + Conversation concept is really smart and this is something that Slack just doesn’t do.

Slack on the other hand is designed to be stand-alone. This means that Slack has been more focused on API’s and integration points to allow third party chat bots to extend the functionality of Slack. While I think it’s ideally suited for small to medium size organizations, companies as large as IBM are using slack with their 350,000 employees. Integrations across GSuite, Dropbox, Microsoft, Box, Zoom, Salesforce and more make it easy to tie many tools together into one conversation.

Remember how I said that communication is a company-culture thing? Well a key reason for that is that these chat tools can makes it easy to give your organization to offer company transparency.

Different teams or departments can have their own channels and make these channels visible across the company. This can make it easy to both find important company information and understand how decisions were made through discussion. This idea of being more public by default is a powerful idea and it allows organizations to move faster.

Conversational interfaces are here to stay because they meet us where we are as people and they foster collaboration in a very intuitive way.


Raising too much money

Two weeks ago Friday, according to Forbes an app called Clubhouse raised 12 million in financing at a post-money valuation of 100Million dollars. This is crazy when you consider that the app has no real users, aside from investor insiders. It’s been called amazing for the founders and company, but raising a ton of money at sky-high valuations can also spell disaster.

Raising too much money can ruin your business, your product, and your vision. Only time will tell if this was a brilliant move by the investors, Mark Andreesen, or a slip-up by the founders.

Lots of startups assume that there’s no such thing as raising too much money, after-all you need money. The crazy valuations can attract talent, buy fancy perks, and allows them to outspend on promotion, and customer acquisitions. But all these moves can lead the company astray and too much of a good thing can cause other issues.

Build a sustainable business

Watch my video on this topic

Too much money can cause you to overspend across the board. At first, this is a ton of fun, and companies who get over-funded go on a spending spree. They get fancy computers, standing desks, hire a ton of people, and often create multiple secondary teams working on secondary products or features. Sounds great, right?

Well, what happens is that the small team that was able to move quickly and get things done with 10 people, starts to drag with the weight of a larger organization. But the real problem is that the larger organization moves the profitability goal-posts.

Getting to profitability

A 10 person software team can get to profitability at just 1-2 million in revenue. A 100 person team may require 15-20 million in revenue to hit that break-even point. Suddenly the millions that you raised is running dry and you have to go back to investors to raise more money. This is where startups can get into even bigger trouble. If the last round was 100M valuation you will need to raise at an even higher valuation.

Two problems with this.

  • #1 – You need to prove you’re worth it. Each time you jump in scale gets even harder. You need to have the product and customer traction to justify that price.
  • #2 – Each time you do this you dilute yourself and you move the goal-posts move again. If your startup can’t grow fast enough, that just means raising ever-larger rounds. You hope to reach escape velocity while never turning a profit but this can also end in disaster.
Magic Leap Raised AR Glasses

How much is too much

One recent example of this is Magic Leap. They raised 2.6B over 9 rounds of financing. They initially hoped to sell hundreds of thousands of headsets but have thus far reportedly sold just 6000. After years of trying to get adoption, they are both attempting to pivot into the enterprise and trying to be acquired. (unsuccessfully thus far).

Smaller startup teams have the advantage of moving quickly, being able to pivot, and actually ship product. As teams get larger companies will spend more time on operations and communication. Large companies have a harder time with rapid innovation and this size is a direct result of investors plowing too much money into a good idea.

Masking Fundamentals

Besides overspending and overhiring the other key problem is that having too much capital can mask fundamentals. Many startups famously create fake traction charts by over-spending on customer acquisitions. How do they do this?

Easy. Spend $1000 the first month on advertising. Spend $2000 the second month and so on….. hey look, our growth is going up each month. We must be growing like crazy! Well sure if your customer acquisition costs are reasonable but not everyone looks at this and some startups will spend hundreds of dollars to get a customer that’s worth a fraction of the costs.

Sometimes startups aren’t intentionally fooling investors, sometimes they are actually fooling themselves. Company problems can be masked with capital.

  • Customers complain a lot – hire a customer support team to hide the problem.
  • Too much customer churn and cancelations – hire a customer success and retention team to keep them around a bit longer
  • If the product is terrible – hire a marketing firm to make a great promo video.

These things may look like they are helping but they are really masking the underlying issues. It costs less to fix the product and have a great design that customers love… but if you have a lot of capital you may have incentives to spend it in the wrong places.

Limiting your options for an exit

The other problem from raising too much capital is that it can limit your options down the road. Let’s look at two companies, both companies have built an amazing MVP and they go to investors looking for money.

  • Company A asks for 1M to give their small team a year of runway to improve the product at a 5M valuation.
  • Company B asks for 10M to significantly grow the team and spend on marketing and give it runway for 18 months at a 100M valuation.

One year later both companies get hit a wall. The tech is harder than it seemed, the market is more competitive but they are approached by a dream acquirer who wants to buy the business for $20 Million.

Company A, gave up 20% equity so they can walk away with $16 million dollar pay-day. The investors in company A made a 4x return on capital, not bad for 1 year.

The founders of Company B probably can’t take the deal. Not only is Company B much less profitable but worse… Even if they could accept such a deal they may get caught by a gotchya-clause called “liquidation preferences.”

These clauses in larger investment deals mean that the investor will agree to the higher valuation, as long as the startup agrees to give the investor a multiple on their money prior to selling. This may mean that the investor gets a minimum of 2-times his investment back prior to anyone else. In this example, if the investor had a 2X liquidation preference, all 20 million would go to the investor and the startup founders would be left with nothing.

Minimally Viable Capital

There’s a lot of press and attention to valuation and the size of funding rounds raised but the focus should be more on the sustainability and the long term potential of a startup. Founders should raise the minimum to give them security in the future and to bring them to long term sustainability and longevity.

Your equity and valuation don’t matter if your startup dies. Get to traction, get to product fit, get to awesome! Then, if your company truly has traction and is changing the world, go ahead. Negotiate amazing terms, raise money to grow your company even faster but be cautious because too much of a good thing could ruin your business.

business startups

Why I became an Angel Investor

I started my business in 2003 after leaving Microsoft and I grew my business to be one of the leading mobile development companies. I was working with a diverse set of companies around the world, building incredible technology. When I sold my business in 2017 I started to think about how I could give back to both the Boston community as well as other founders, leaders, and entrepreneurs.

Investment stages and startup stages

Angel investors are typically people who make investments from 5K-100K in early-stage companies. Companies at this stage typically have an idea, they have a team and maybe they’ve made some traction or progress but they need additional help to get to the next stage of growth. They often are too early for VC’s and don’t make enough to be profitable on their own… The TV show Shark Tank popularized some of the ideas but angel investing has been around since the late 1970’s, and most investors aren’t as predatory or quite as “sharkie”.

Angel investing isn’t adversarial and the drama that unfolds on TV in 15 minutes is often more complex and takes weeks to sort out in real life.

One of the reasons I wanted to give back and help other entrepreneurs and CEO’s is because entrepreneurship and being CEO is incredibly lonely. It’s an amazing job and really rewarding but being a successful leader means constantly solving problems and having the entire weight of a company on your shoulders. This is both exhilarating and incredibly stressful.

It also means that there aren’t too many people you can talk too. You can’t talk to your employees about your business problems and your family and friends wouldn’t really understand the challenges. No CEO knows all the answers and having good mentors and business partners and investors helps companies succeed along that journey.

Angel investors invest not just money but time and expertise in helping companies. Most importantly they can be a sounding board and compass for entrepreneurs blazing a trail.

Why don’t I just invest in the stock market? That seems a lot easier? It is a lot easier and a lot less risky. I do invest in the stock market but it’s also less rewarding. While I can make money in the stock market, I don’t really feel like I’m advising the founders and CEO’s. Elon, Bezos, Sundar, and Satya are probably having their own challenges but they haven’t called me up… Just sayin’.

As a CEO you don’t really like anyone telling you what to do because you like to run the show, and if your business has any success you definitely don’t want people telling you what to do. But you also don’t have a lot of people to bounce ideas off of.

The second reason is to make an impact. When you start a company, or run a company you’re solving a problem and in most cases you’re helping either people or other businesses. As a founder you can really only focus on one big problem at a time but as an angel investor you can participate and help multiple companies working on problems you care about. I’m interested in the environment, alternative energy, artificial intelligence, robotics, and more. Angel investing allows me to have an impact across a wide range of fields and technologies.

And lastly… Making money. Yes, making money is important but I list it last for a reason. Investing in companies takes time. You often don’t get your investment back for 7 or more years so short-term financial returns isn’t ideally suited for angel investing. The returns for an investment can range from losing your entire investment in a company to making a hundred times your investment. The range is very broad because many companies don’t make it.

Example returns across five scenarios assuming twentyfive companies

If I invest in 25 early-stage companies I can expect that 21 won’t make it, two will do Ok, and if I’m lucky, one will be a huge hit. Lots of angel investors don’t make money and while my goal is to do better than average I think that only by understanding the models for success can I hope to do better.

So far we’ve hit three things:

  1. Helping founders
  2. Making an impact
  3. Financial returns…

And the reason that financial returns are important is that it can help more founders and make an even larger impact.

So, if you’re a startup founder, an entrepreneur looking for advice, funding or help. Please follow along, reach out, and let’s make something awesome!


Tello EDU 2020

It’s amazing how far drones have come and in 2020 the Tello Edu drone is perhaps the lowest cost beginner drone that allows you dive in, take pictures and fully program a flying drone. For those learning about Drones and not wanting to break the budget, it’s a great starter option. The Tello EDU is also very affordable for those learning about robotics, AI or image recognition.

If you get intro drones, you’re going to crash it. That’s just how it goes, you may as well start with a low cost starter option.

The 2020 Tello costs just $129 and is sold by DJI, it’s built by Ryze technologies and comes packed with a camera capable of doing 720p video or 5MP images. You’re able to program the drone using Swift, Python or Scratch and the Tello SDK allows for even more.