Killer Tech Tools That Make My Business Better Than Yours

Serial entrepreneur Jason Calacanis reveals his four favorite productivity tools that can boost a business quickly for less than $1,000.
May 02, 2013

When I started building companies in the '90s, the only tools designed to help startups grow were "productivity apps" like Microsoft Office and Quickbooks. They were helpful, but they only solved very basic problems like math, bookkeeping and letter writing.

They didn’t address high-level stuff like ideation, analytics, hiring, CRM (customer relationship management), time tracking, project management, customer feedback and—gulp!—employee motivation and feedback. If you wanted software to do those things, you needed to hire three or four people and customize software packages, which typically started in the six-figure-and-up range.

Today? Today you can have all eight of those functions for—wait for it—under $1,000 a month. Most importantly, they can each be set up and learned in under a day, and managed by existing team members—without dedicated staff—in a couple of hours a month.


Here are my four favorite startup tools:

1. TheResumator: This SaaS offering takes resumes out of Gmail and Excel spreadsheets, cleans them up and organizes them. You simply send potential candidates to a URL to upload their resumes and then the workflow takes over, with your team members categorizing, rating and scheduling interviews.

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My favorite feature? You can require candidates to answer a couple of questions before they are allowed to upload their resume. This reduces the number of “drive-by applications” and tells you if people can think on their feet.

2. Harvest: Time tracking is a very touchy subject in the employment space, and you have to be very, very careful implementing it if you’re not in advertising, legal or consulting (where it’s standard). Time tracking asks team members to report on which projects and tasks they are working on down to the quarter hour.


It seems annoying, but it actually isn’t a big deal. It adds about five minutes to each person's day—max —since most folks work on fewer than 10 tasks a day. The information you can get from it can be unexpected. For example, we realized that one of our video shows was costing eight times another, with two more sitting squarely in between. When drilled down, we figured out what the more efficient shows were doing, and applied those best practices to all the other shows. 

Additionally, we went to our distribution partner and said, “Look, this is costing us more and here are the numbers—we need a better deal.” We got it!

Now, you will get standard objections like “I’m too busy to do this” and “You don’t trust me?” The first objection tends to come from high performers, who will respond properly to "I understand you’re slammed, but if you do this, it’s a short-term cost for a long-term benefit, because we’re going to show exactly how much more effective you are than everyone else—and you can use that in your next review!"

The “You don’t trust me?” protest tends to come from "eeyores" or low performers. When they respond this way, you should look them in the eye and say, “We wouldn’t have hired you if we didn’t trust you. This is for the good of the team.” Then say nothing. If they whine some more, you can use the metaphor of athletes who track every metric under the wisdom of "If you can measure it, you can manage it." If they still complain? Well, it might just be time to hit the eject button on that employee.

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3. Project management tools: I’ve used PivotalTracker and Trello in the past, and right now I’m using Trello, as my teams seem to like it slightly better. In this Web-based software, you add a bunch of tasks you need to complete for your various projects. People claim them, discuss them, prioritize them and—hopefully—complete them. It really helps take ideas and tasks out of people's notepads and Google Docs, and organize them. Once you start using a program like Trello, there's no going back.   

4. 15Five: I love this employee feedback provider so much, I invested in it. The concept is simple: Everyone answers a couple of questions, like "what was your big win this week?" and "what’s frustrating you?" at the end of the week in under 15 minutes. Then managers review their direct reports' answers in under 5 minutes. Fifteen minutes to write, five minutes to review.


In the year I’ve been using this, I’ve learned exactly how annoying the guy laughing at YouTube videos is to the people sitting around him (very), and how much people appreciate the high-quality coffee machine. I also found out which people were consistent "eeyores" and which ones were culture builders. This led to some great interventions by managers who confronted the negative folks, giving them two great options: "Stop being a victim or find a place better suited to your unique style!" Your employees will lie to your face when you say, “How's it going?” but they will—shockingly—tell in detail how they feel about things if you present them with a Web form. 

What tool do you wish existed for $99 a month?

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