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.

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!


How to start a company with no money

Starting a business without initial capital is a process of building a stable foundation while minimizing risk.

There are three things needed to start a company:

  1. Money
  2. Customers
  3. Product/Service

Since we’re doing this without money, we’re left with just Customers and Products. The easiest way to get this started is with a side-hustle. The main idea is that you keep a stable job to provide you regular schedule and the financial stability and work on your business during nights and weekends.

Your side-hustle doesn’t have to be the exact business that you will start but it should move you in the general direction of your interests. If you think your business will be in the food or restaurant space consider delivering grub-hub as a side-hustle. Want to get into real estate? Look into being an AirBnB host. If you’re starting a beverage company, consider working at a bar or restaurant at night.

Think of your side hustle as both some financial capital but also as market research. There are a lot of examples of entrepreneurs getting started this way. Michael Dell started his computer business being a student and having a side-hustle of putting together computers for your friends.

Daymond John, the founder of clothing company FUBU, was working in Red Lobster while he was getting his business off the ground selling hats on New York street corners.

The founder of Mattel sold picture frames as his main thing and used the scraps of the picture frames to start building and selling dollhouses.

Lara Merriken, was working in Whole Foods stocking shelves working on her product the Lärabar, which gave her insight into how Whole Foods works and it also gave her access to store buyers willing to try her product. This access ultimately led to her big break.

Starting your business as a side-hustle gives you the advantage of financial stability but it also gives you a unique view of business problems. It may also give you access to customers.

If you’re trying to start a company with little or no money one thing you try to do to get initial cash flow is to get a customer to pay upfront. How do we do that? You build a prototype or sample.

Prototypes don’t have to be expensive, they can be drawn on a piece of paper, cut out of cardboard, hand made models or recipes baked in your oven. Certain businesses are harder to start without funding but most business ideas can be prototyped.

If you’ve built a prototype or sample of your product then services like Kickstarter, Fiverr or Etsy can give you a platform to sell products your product directly to consumers. These types of services require very little or no up-front capital. You can get customers before committing to a lot of financial up-front risk.

If you have a service business you may also be able to charge an upfront-deposit or down-payment giving you initial cash-flow. This is common in many consulting, construction, and subscription businesses.

Your early samples and prototypes can also give you customer feedback on what people like or dislike about your product.

Initial sales are unlikely to have a significant initial financial impact but they will help you continue to improve your product and they will get the initial flow started. Initial sales are sold one-by-one, so expect to get personal when you start the business. As your product or service gets out into the real world, you’ll start to develop word of mouth about your business or product.

For companies that have Money – they can spend money to get customers. But starting a company with little or no money, you need to make your products really great to get the word-of-mouth and attract more customers.

As the business grows, the revenue flow starts to increase and you’ll be able to spend more on growth, hiring, and talent. Ultimately every small business can be the catalyst for a larger one and the hardest part of starting a business is actually starting.

Good luck on your journey!

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Elon’s MasterClass in entrepreneurship

Musk is one of the most prolific entrepreneurs of our generation has started, led, inspired or invested in not just one business that grew to over a billion dollars in value but at least four (Paypal, SpaceX, Tesla, SolarCity). In addition, he’s also currently incubating ideas with, Hyperloop, Boring co, Starlink, and Neuralink (each having similar scale potential).

There are four key aspects that make him very different from a typical leader:

  • Clarity in vision
  • How he solves problems
  • How he leads
  • How he engages both with customers

Elon’s not perfect and there are certainly lessons to be learned from some of his missteps but I’m going to focus on four key areas that every entrepreneur should study:

Clarity in vision

Many companies lack a basic vision and mission statement and many that do have a vision statement don’t use it to run the company. Let’s look at the clarity of the mission for Tesla and SpaceX’s:

Accelerate the world toward sustainable energy

Tesla Mission Statement

Note that it says nothing about electric vehicles, batteries, solar, cars or trucks. Its clarity in purpose gives the company long-term direction on the purpose of their products and services.

This is true not only of Tesla but also of Space X…

Make life multiplanetary.

SpaceX Mission Statement

It doesn’t talk about rockets, mars, astronauts or satellites. It’s focused on the long-term goal of where the company is going, in this case to Mars.

The clarity in vision helps as an internal north star but it can also help the business grow, attract talent and position itself among a crowded field of competitors.

Elon went further than just the mission statement and also publicly outlined what he described as the “Master Plan,” explaining in public how he would go step-by-step to move closer to his vision.

Build sports car
Use that money to build an affordable car
Use that money to build an even more affordable car
While doing above, also provide zero emission electric power generation options

Don’t tell anyone.

Elon Musk – 2006 in Tesla blog post

I can’t find a single other public company that has so clearly outlined its vision and how it’ll get there. The clarity in vision and mission give Tesla and SpaceX an edge because it both attracts the right talent and it gives all employees more clear direction in terms of “what’s right,” for the business. This allows the business to move faster at scale in the right direction.

Solving problems on first principals

The notion of first principals is breaking down a problem to it’s most basic elements. Musk’s background in physics helps him in this respect but it’s applied to multiple aspects of his businesses.

Musk explains that assumptions about the costs of batteries could be broken down into the chemicals that compose a battery and the raw costs of those chemicals.

Rather than asking what is possible from a business standpoint, he asks what is possible from a physics, chemistry, mechanical perspective. This gives him theoretical maximums and minimums and allows him to challenge his respective teams with the bounds rather than the market competition. This has allowed him to push the state-of-the-art on solar, battery production, rocketry and other technologies.

Leadership Style

He sets aggressive deadlines for his teams ensuring that his companies are always working on the tasks that most directly lead to results associated with those deadlines. Tight deadlines take advantage of Parkinson’s Law.  The idea behind the law is that: “Work expands so as to fill the time available for completion.” Even though these deadlines are often missed the deadline itself forces focus and prioritization and critical decisions that are often lacking in companies that set far out deadlines.

Musk welcomes competitors and competition. He’s expressed the willingness to go head-to-head with Ford, VW, Porsche, and Boeing. While some leaders shy away from competition Musk leans into these scenarios as it challenges him to produce the best products and technologies.

Working with Customers

Musk interacts directly with customers on twitter often engaging and inviting critics to complain directly. While he’s been criticized for this, it does give him a direct view into how customers view his products and where the business needs more attention.

Many CEO’s and leaders don’t provide visibility or direct engagement leaving such tasks to customer support or marketing departments. Direct engagement requires vulnerability on the part of the CEO (you need a thick skin) but the positive aspect of this engagement is that he’s able to keep multiple divisions and departments accountable for the quality that he’s looking for.

Lastly, Elon Musk likes to have fun. He injects fun and fun features, jokes, easter eggs and space balls references into his daily interactions, he doesn’t take himself too seriously even though he works incredibly hard. This sets a tone for both employees and customers in terms of what to expect from the products and the company in terms of fun.