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Chapter 22 Bonus Section: What We Used for Our Internal Systems When We Started Bolster

The company was formed on April 1, 2020, in the midst of the COVID‐19 pandemic. As everyone was going to be working remotely for the foreseeable future, it was very important to establish the tools and operating systems as soon as possible. We had the advantage of receiving some support from our early investor High Alpha's venture studio on a few of the tools and processes. We started to put these systems into place on day one and completed almost all of this in the first couple of weeks. This of course is very different than twenty years ago when we started Return Path, but I also feel it has come a long way the last five years. This section will become dated as systems are improved and new choices are established but I thought the overall process will have some interest.

Selected Systems

Communication: Slack

We created a free account. Planned to upgrade when we hit feature requirements. In the early days, we kept channels to a minimum. General was reserved for rare company‐wide events that don't need context. Water Cooler for open conversations, random fun facts, and pictures. Then let it be organic with curation as it grows.

We established integrations with Trello, Outlook, and Zoom. The Zoom Integration enabled quick video chats to happen with a simple/Zoom command. The Outlook plugin enabled a nice schedule within Slack and put a calendar flag in your status to let other Slack users know that you are currently in a meeting. With the Zoom integration, if a Zoom meeting went on a long time, it kept the flag active. When the meeting was over, the flag cleared.

Project Management: Trello

We created a free account. Trello has a very good free platform for a small number of users and boards.

Focused one board to manage the activities of the eight of us. The first column was a “How to use this Board” card, the “Weekly Goals” card, and the parking lot for cards to be assigned/discussed. Then each column had cards for each functional area with appropriate people as members on the card. We used labels for “Need to get done this week,” “Blocked,” and “Ready to Review” to promote asynchronous review and work.

Email and Calendar: Exchange

Cost: $4/month per user.

This was a bit of an unusual approach as most companies will just start with the entire GSuite. We decided to start with Exchange as some members of the team had a strong preference for the email/calendar functionality of Exchange and Outlook. It generally works well if you are OK with Outlook and Outlook has strong iOS apps.

File Storage/Management: Google Drive Enterprise

Cost: $8/user per month plus $0.04 per GB per month, estimated $900 a year.

Certainly going with different systems for email and document management is not ideal. We wanted to give it a try as we had a strong preference for Google Drive. The OneDrive/Sharepoint experience we had in the past was not a positive one and effective file‐sharing/storage is important to get right on day one. We established about eight shared drives that mirrored the functions of the business. We also tried to ensure that we started right away with a logical document storage process, so we established a number of official folders for things like corporate documents, financials, and invoices. We also were able to install the Google Drive desktop apps so that the access to the files was as easy as if they were local files.

Video Communication: Zoom

Cost: $2,000 per year for up to 10 licenses.

We felt Zoom had clearly the best technology and workflows for a startup. We could have gone with a $1,000 plan but we wanted some of the features included in the Pro license. We planned on integrating Zoom inside our platform so may have to adjust the license in the future. This was a critical piece of software to help us effectively work together and conduct nearly 100 external meetings in the first month of operations so we wanted to ensure we had the best technology. We did not go with any of the other features of Zoom like Zoom Room or the softphones.

Web Analytics: Databox

This was purchased at the suggestion of our investor High Alpha as it works well with Hubspot.

System Password Management: 1Password

Cost: $50 for the year and first 6 months free.

To ensure centralized storage of system and administration passwords, we created a 1Password account to store passwords for all of our corporate systems and production technology on AWS.

Product Storyboarding: StoriesOnBoard

Cost: $300 for the year for one edit license (and many viewers).

Given how distributed we are and our future product development, we thought we would find a tool that helps storyboard/lean canvas very helpful. Plus, it integrated with Trello.

Financial System: QuickBooks

Cost: $65 a month.

We were planning on having a third‐party handle the back office for bookkeeping so just went with the basic approach they were familiar with. The key adjustment was revising the Chart of Accounts to match the business and ensuring the key integrations with Bill.com and Expensify were completed. A quick note that although we did not set up any sales tax software at this point as we were months from any revenue, and perhaps longer from the type of revenue that would require sales tax collection, we did ensure that when were ready, we could plug into our systems quickly and painlessly. Fortunately, just about every sales tax solution will plug into QuickBooks and we made sure our internal accounts were ready.

Accounts Payable: Bill.com

Cost: $1,000 per year.

This may be a little early for this software given the small numbers of vendors we will have and we are months away from revenue. But given the cost, we thought we might as well integrate early on and help develop complete documentation of all of our AP management and give us the option of using their invoicing in the future.

Expense Management: Expensify

Cost: $1,000 per year.

Another nice to have but, given the cost and the ability to start from day one with consistent expense tagging and documentation, we felt it was worth it. Easy to set up. We have a policy where the COO approves everyone and the CEO approves the COO. Expensify also has the ability to directly refund to an employee's bank account once the expense is approved so the process will scale well.

Equity Management: Carta

Cost: Startup package, price varies.

We had a lot of experience with Carta and put a lot of value on having the equity ledger on Carta from day one. Initially not using them for either 409a or Board resolutions. So just need the basic package for about six months and plan to eventually move to them for 409a valuations.

CRM: HubSpot

Cost: Their startup package, about $1,000 for the year.

Typically, companies will go with Salesforce.com, but one of our investors had a lot of experience using HubSpot for startups and our early workflows for our CRM were basic enough where the tool itself wasn't as important as building a solid foundation.

HRIS: Gusto

Cost: $1,600/year.

We wanted to use a lightweight and basic HRIS at this stage that could scale for our early planning and members of the team had a positive experience with Gusto. In addition, Gusto was able to issue 1099s for any contractors we used and can integrate our payroll and benefits administration in all of the states we were planning on being in for the foreseeable future.

Calendar Management: Calendly

Cost: Free or $10/month/user for more features

This has solid integrations and ease of use. We needed to set up a lot of calendar events in the early days as we had to do 100s of market interviews and found Calendly helpful as it integrated with Outlook and Zoom.

Payroll: Gusto

Part of the HRIS.

401k Provider: Guideline

Cost: About $1k. $39/month + $8/PartEmployee per month

We liked Guideline's approach of no AUM fee and really just a place to buy Index funds. This approach minimizes the overall expense ratio of the plan and fits well for what we wanted in a 401k. If we had not already funded the business, we likely would have waited before spending money on this benefit. It also integrated seamlessly with Gusto.

Insurance Provider: Vouch

They had a really easy workflow to get the basic General, EPL, E&O, and D&O. The price was less than what we had thought it would cost to get the basic insurances needed for our operations. Very effective for a startup.

Key Processes Established

 Documents to track

 Document storage

 Domains and aliases

 Purchasing and asset management

 Corporate cards

 Social accounts to build

 409a/83b valuation

 Trademark search

 Brand positioning

 Vendor tracking

 Asset management tracking

 Chart of accounts

 Incorporation/EIN/W9

The total is under $10,000 for the first year.

Startup CXO

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