Entrepreneur's Toolkit: Tools and Technology for your Startup - Part 2

In part 1 of this series, we covered software for productivity, chat and collaboration, audio video conferencing and file sharing. Without further ado, let's continue.

Password Management

Keeping your company's data secure across the various SaaS tools and technologies you use is critical. At the heart of that is good password management. Some basic things you should be doing to protect yourself and your company:

1. Ensuring that employees always use strong, unique passwords for each site

2. Storing all passwords, whether they be for individual accounts (bound to a specific person), or shared accounts (the same account is used by multiple people in the company) in a password manager

3. Using 2 Factor Authentication (2FA) wherever possible 

A password manager helps with the first 2 of those.

LastPass

Like all password managers, LastPass allows you to remember one password (ie your "last" password) and store everything else inside LastPass's secure password vault. This means you can have really long, complicated and unique passwords for each of your sites, and LastPass does the remembering so you don’t have to. It has browser plugins along with a mobile app that all sync together, so you can easily and securely access all of your passwords from wherever you are. LastPass's Team version allows individuals to keep track of their passwords, as well as setup company-wide shared folders to securely share passwords across the team. It also has a variety of different security policies you can set up, for example, ensuring that everyone must use 2FA to get into their LastPass vault. Pricing for LastPass teams starts at $4/user/mo.

1Password

1Password is another password manager similar to LastPass. Also $4/user/mo for their Teams product.

Dashlane

Dashlane is another option. Similar feature set and price point as LastPass and 1Password.

My Recommendation: LastPass

All of these options are pretty similar. Out of familiarity, I'm going to recommend LastPass. But all of these are capable products and will give you the core features you need for password management across your team.

Whatever you do, you must provide a password manager for your team and insist that everyone in the company use it to store their company-related passwords.

Electronic Signature Service

As part of actually forming your company, you're going to need to sign a bunch of documents. And that's just the beginning. To manage all of this, you're going to want an electronic signature (sometimes calls eSignature or e-sign) service.

DocuSign

DocuSign provides online electronic signature services. Pretty straightforward, decent UI. Pricing starts at $10/mo for a single user, $25/user/mo for a multi-user plan.

Adobe Sign / EchoSign

Way back in 2011, Adobe acquired Echosign, and has since rebranded it Adobe Sign. Similar feature set to DocuSign, and priced at $10/mo for a single user, or $30/user/mo for multiple user plans.

HelloSign

Recently, Dropbox acquired HelloSign. Presumably it will eventually be rolled into the main Dropbox product, but for now it remains a standalone service. HelloSign's pricing is a bit more attractive than Docusign or AdobeSign. There is a limited version for free, a Pro version for $13/mo and a Business version for $40/mo for up to 5 users - quite a bit cheaper than an equivalent plan from Adobe or Docusign.

My Recommendation: DocuSign

I've used both DocuSign and Adobe Sign. Between the two of them, I prefer DocuSign, but fundamentally, they're both going to give you the same end result: electronic signatures. HelloSign has a compelling price point, so if I were starting something from scratch today, I'd check it out as well.

Accounting

It's one of the last things that you want to deal with as an entrepreneur trying to conquer the world, but it's necessary.

QuickBooks Desktop

Do not use QuickBooks Desktop - it is the devil!

But seriously, when I first started my own company, QuickBooks was the de facto standard for small business. Every accountant is familiar with it, however, for ordinary people, I found it extremely un-intuitive and one of the ugliest pieces of software I have ever used. I haven’t touched this in years, but I assume (hope?) they have changed the UI, but regardless, a desktop version means you've got your accounting file stored locally, which makes it difficult to share with your accountant and bookkeeper. You also need to make sure it's getting backed up (which you should be doing anyway).

Steer clear of this product and go for a hosted solution.

Xero

Xero is an online QuickBooks alternative. It’s simpler, fully online and easy to invite other team members, bookkeepers and accountants to collaborate on your books. It is however rather limited in its feature set. If your business is simple, you'll probably be fine, but I've found problems as soon as I start getting into more complicated areas of accounting (or more accurately, when my bookkeeper or accountant tells me that Xero doesn’t support something that I would like to do, like certain kinds of reporting). Pricing starts at $9/mo, but realistically you'll be looking at the $30/mo or maybe $60/mo version. Unlike the software we've explored thus far, this is not priced per user, but just one charge for the company.

QuickBooks Online

Long after I had adopted Xero, QuickBooks came out with QuickBooks Online, an alternative to their desktop product. Based on my prior experiences with their desktop product, I stayed well clear. However, recently, I was trying to do some reporting on expenses with Xero and my bookkeeper informed me that it was not possible with Xero, but could be done with QuickBooks online. I tried it out, and was pleasantly surprised - QB Online as a good UI, it's easy to use, and it did have the reporting ability I wanted. Pricing starts at $20/mo, but you'll probably be looking at the $40 or $70/mo version.

My Recommendation: QuickBooks Online

At present, I use Xero for my companies, but I think if I were starting something new today I'd probably go with QuickBooks Online (I literally never thought I'd say that). This is primarily due to the number of limitations I've run into with Xero. Something that seems simple, and should be doable, is often not. Xero has evolved over the years, but it seems to move at a snail's pace compared to other online services I use. At this point, I’d give QuickBooks Online a shot.

Virtual Phone Number

As a startup, you probably don’t need a full-fledged PBX phone system. However, you do need a business phone number. Even if it's just for the myriad of accounts you need to establish with various government entities like your state's department of revenue and the city in which you operate. You may also want one to publish one on your website for sales and support purposes.

Google Voice

If you're just looking for another inbound phone number that's not your own personal number, Google Voice has a free personal offering that works great. For example, you create a Google Voice number, and when people call the number, the call gets forwarded to your cell phone.

Grasshopper

If you're looking for professional phone presence, Grasshopper might be your ticket. When someone calls your company's number, they hear something like "Welcome to Awesome Co. Press 1 for sales, 2 for support etc…". Then you can setup a variety of different extensions that forward to people's cell phones according to various rules, along with a whole bunch of other features. It's pretty capable, but kinda pricey starting at $29/mo.

My recommendation: Google Voice Free then Grasshopper

If you just need to publish a business number and don’t intend to use it much, start with Google Voice personal version which is free. When you get to the point that you need to publish a phone number on your website and handle inbound calls for sales, support etc… Grasshopper makes sense.

As a side note, if you do need a full-fledged internal phone system, there is also Google Voice for business that gives you a cloud-based phone system which is tightly integrated with G Suite. Pricing starts at $10/user/mo.

General Project Management

Remember that never ending list of to do items I mentioned earlier? You're going to need somewhere to keep track of all that stuff and collaborate with the rest of your team. There are more pieces of project management software that you can shake a stick at, but below are 2 that I like the best.

Note - this is not software project management, which I'll cover below.

Asana

Asana is a modern, easy to use, online project management system that can start simple and scale up to handle more complex scenarios. Accessible via their website or mobile apps to help keep everyone in sync. The free version allows for up to 15 people, so it will take you a long way before you need to upgrade to the paid version, which starts at $10/user/mo.

Trello

Trello is easy to use, flexible project management software with a cool UI. Conceptually pretty similar to Asana, but they both take quite a different approach. Free initially, then starting at $10/user/mo.

My Recommendation: Asana

Personally I like Asana for most general project management tasks, but Trello is also a worthy choice. Use what you like best.

Software Project Management

Managing software development is different than general project management, thus it deserves its own tool. Similar to general project management, there are so many choices in this area, it's easy to get stuck in analysis paralysis. Here's a few of the most popular products out there to help your narrow down your search.

Pivotal Tracker

I've been using Pivotal Tracker, an agile project management tool, for many years now, and I like it. It's straightforward to use, constantly evolving, and designed to support an agile development workflow. There is a free version for up to 3 people and 2 projects, then you’re into the paid versions starting at $12.50/month (for 5 users) or $30/mo plan (10 users). Pricing scales up from there for bigger teams.

Jira

I don’t use Jira myself, but it's a popular issue tracking tool with a lot of features. $10/mo for a team of up to 10 people, then pricing jumps up from there to $77/mo for 11 people.

GitHub Issues

The king of source control, GitHub, has a built-in issue tracking system as well. The fact that it's built right into GitHub makes this a compelling choice if you're using GitHub for source control. Even though I use GitHub for source control, I don’t think it's project management features are as capable as Pivotal Tracker or Jira.

My Recommendation: Pivotal Tracker

Personally, I like Pivotal Tracker. I've been using it for nearly 10 years across a variety of different projects. It's simple to use and quite prescriptive leading you down an agile development path, which I think is a good thing.

Stay tuned for part 3 for more recommendations on tools and technology you'll need for your startup.

Entrepreneur's Toolkit: Tools and Technology for your Startup - Part 1

When first embarking on your startup journey, there is a seemingly never ending list of things to do, and everything on that list is demanding your time and attention.

In fact, before you even formally start your company by creating a C-Corp in Delaware (or whatever type of entity you're forming, and wherever you're locating it), there are a lot of things you should be doing, for example:

• Refining your vision

• Validating your vision and idea with potential customers

• Building prototypes and starting work on your minimal viable product (MVP)

• Selling your product to customers - if you've got customers who are willing to pre-pay for your product, knowing that it won't be available for X months, that’s a great sign that you're solving a real pain point

• Building your team - or at least talking to people who you may want to be part of your team as things progress

During this process, you're going to need to start using various different pieces of tools and technology to collaborate with people, manage the development of your MVP and communicate with customers.

Once you formally start your company, you now need to deal with things like accounting, tax filing, payroll and a whole bunch more.

To help manage all of this, you're going to need tools and technology. There are a myriad of choices of SaaS based tools and technology out there. It's time consuming and overwhelming to try and sift through them all and figure out which ones you want to try, then which ones to adopt.

I've spent countless hours over the years researching, trying out, and then actively using different pieces of software across various startups. To help give you a head start, here's my list of tools that you may want to check out.

Since there is a lot to cover here, I've broken this post up into 4 parts:

• Part 1 (this part): productivity, chat and collaboration, audio video conferencing and file sharing

• Part 2: password management, electronic signatures, accounting, business phone number and project management

• Part 3: customer relationship management and support, email marketing, website and building your own database

• payment processing and a couple of other bits and pieces.

• Part 4: HR and payroll, payment processing on your website and in person, payment vendors in the US and internationally

Productivity Suite (email, word processing etc…)

Selecting a productivity suite to give you customized email (eg @yourocmpany.com), word processing, spreadsheets, presentations etc… is going to be one of the first things you need to do. It will also drive the other choices you're going to make. Fortunately, there are really only 2 options you need to worry about. 

Microsoft Office 365

Microsoft's offering in the productivity space is called Office 365. Depending on which package you choose, it includes hosted company-branded email via Exchange along with desktop and online versions of Outlook for email, Word, Excel, PowerPoint etc… On their website, you'll find 3 different plans for personal, 3 for small business and at least 4 for enterprise. It's confusing, but here's the summary: for a startup, you'll be looking at the "Business" section:

Plans start at $5/user/mo, but you'll probably want the $12.50/user/mo Business Premium version - this gets you cloud hosted company email, all the Office apps (online and desktop versions) along with a bunch of other stuff we'll discuss below.

G Suite

G Suite is Google's competitor to Microsoft Office 365. It's a very capable offering and many companies use it. However, all of Google's apps are browser based. I prefer the richness of a desktop app along with its offline capabilities (I spend a lot of time on a plane). Google's Docs, Sheets, Slides offerings are good, but they're not as good as Microsoft Word, Excel and PowerPoint respectively. Google's pricing packages are a lot simpler:

Starts at $6/user/mo for the Basic version, but you'll probably want the $12/user/mo Business version. 

My Recommendation: Office 365

I prefer the desktop versions of Word, Excel PowerPoint to their online equivalents or Google’s offerings, so that puts me squarely in the Office 365 camp. But to be honest, either of these options are good products. Choose whatever you're most comfortable with.

Chat and Collaboration

In many ways, your decision regarding a productivity suite will influence this decision quite heavily.

Slack

Slack is a tool for team collaboration and instant messenger-style chat between team members. Slack rose to popularity in recent years sparking competition from Microsoft and Google (see below). Slack would claim you can replace email by using it. Personally, I don’t really buy that - no matter what you do internally, you'll need to communicate externally with customers and partners using whatever they use - which is email. I also think email is a better tool for longer form communication. Instant messaging is useful for short messages and quick responses. There is a free version, but if you need more features you'll be starting at $6.67/user/mo.

Microsoft Teams

Teams is Microsoft's Slack competitor. Deep ties into the Office 365 ecosystem and already included for free in various Office 365 plans.

Google Hangouts Chat

Hangouts Chat is Google's Slack competitor. As you would expect, it's got deep ties into the G Suite ecosystem and already included in G Suite plans.

Skype

If you're looking to save money, Skype can also be used for instant messenger-style chat. It's more geared towards personal communication, so not optimized for business chat. It's ok for very small teams, and it is totally free, so there's that.

My Recommendation: Free version of Slack then Teams/Hangouts

Slack is a very popular choice, and the free version is great for small teams. However, when you start to exceed the limits of the free tier and need to move to the paid tier, it's tough to justify $6.67/user/mo if you're already paying ~$12/user/mo for your productivity suite that includes equivalent . You'd be increasing your per user cost by 50% per month. Slack is arguably ahead of its competitors at the time of this writing, but Microsoft and Google are pouring probably hundreds of millions of dollars into catching up. Is Slack worth the extra money? Probably not.

After running into the limits of the free version of Slack, I'd move to whatever your productivity suite includes, namely Teams or Hangouts.

Audio and Video Conferencing - Internally Within Your Team

You'll need tools to do audio and video conferencing within your team.

Slack

Slack has audio and video conference ability built in, although I've found the features and quality don't match up with the below offerings. I'm sure it will improve over time.

Teams

Teams has this capability built in. In the early days, it was impossible to invite people outside your organization, for example, contractors without a @yourcompany.com email address, to join a meeting. That was rather problematic. They've fixed that now, and Teams is a good choice for meetings within the team (meaning employees and contractors). It's also included in various versions of Office 365.

Google Hangouts Meet

Hangouts Meet is G Suites audio and video conferencing offering. Included in your G Suite subscription.

Skype

If you're penny pinching, and working with a small team, you can use Skype totally for free. You will need to have each team member add the other team members into their contact lists to easily initiate calls, and everyone needs a Skype account.

My Recommendation: Teams or Hangouts

Go with whatever your productivity suite offers here.

Audio and Video Conferencing - Externally with Customers and Partners

Besides internal communication, you're going to need to communicate with external customers and partners. While you can technically use any of the above "internal" tools for this, they're not (yet) a great solution to the problem.

Zoom

Zoom has risen to be one of the dominant video conferencing platforms in recent years. It's super simple and easy to use, and importantly, doesn't require your participants to jump through a lot of hoops to get into a meeting. Participants will need to install an app to access the meeting, but that’s free and easy to do for their PC, Mac, iOS or Android device. There is a free version limited to 40 minute meetings, so you'll probably want a paid version starting at $15/mo. You don’t want to be cut off at 40 minutes during an important customer presentation :/

My Recommendation: Zoom

For external meetings, you can't beat the simplicity of Zoom. It's just a better user experience compared to Hangouts Meet, Teams or Skype. Hangouts Meet is pretty good, followed by Teams then Skype for this purpose. See if you like the experience included with your productivity suite, but if not, go with Zoom. 

File Sharing

This is another area heavily influenced by your choice of productivity suite.

Dropbox

Dropbox was one of the first companies to simplify file sharing and make it really easy for individuals. They started with a personal product so you could access your files from any device, and they've since expanded their offering to include features for business, both large and small. Microsoft and Google, along with a ton of other companies, also compete with them. For a team version of Dropbox, you'll be looking at $12.50/user/mo with a minimum of 3 people, so at least $37.50/mo.

OneDrive for Business

OneDrive for Business is Microsoft's offering. It’s biggest selling point is that it's included for free with various Office 365 plans. However, it's actually based on SharePoint, and while SharePoint is a good product for enterprises (it has lots of enterprisey features), it's clunky. Microsoft has tried to put a nicer interface on top of SharePoint to make it look more like the consumer version of OneDrive (which is actually really good), but they are actually totally different products.

Google Drive

G Suite's file storage solution is called Drive. Similar in concept to One Drive for Business, included with G Suite.

OneDrive Personal

If you're penny pinching, you can use Microsoft's OneDrive Personal product and setup shared folders to share files with your team. OneDrive Personal is simple and easy to use, but you'll be missing out on a lot management features you'll want as your team grows.

My Recommendation: Dropbox if you want to spend the money, OneDrive for Business / Google Drive otherwise

If you are willing to spend the money, I think Dropbox has the best product in this space. But at $12.50/user/mo with a minimum of 3 users, it's pretty spendy - you're basically doubling the cost of your core productivity suite.

Is it really worth the extra? Similar to chat and collaboration with Slack, you'll need to determine if it's that much better that you are willing to spend more money on it. If you are happy with whatever is included with your productivity suite, ie OneDrive for Business or Google Drive, go for that instead.

Stay tuned for parts 2 and 3 for more recommendations on tools and technology you'll need for your startup.