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Sales Has A Bad Rep. Here’s How To Beat It!

Sales has a bad rep. Maybe it is because of how movies depict sales people (think: Wolf of Wall St. or Glen Gary Glen Ross) or because the common consumer only encounters them when they buy a car.

used car salesman

However, in selling software, specifically SaaS (recurring yearly payments), the pushy sleazy stuff just won’t work. This is because the customer will just cancel a few months in making the entire deal completely useless.Therefore it isn’t worth even talking about your product unless you can identify a problem that the customer has that your product can solve for them.

It’s All About Solving Problems

Here is my process:
1. Before I go into a sales demo. I spend some time to analyze their website and look for opportunities.
2. When on the call, I ask specific questions like “what are your marketing goals”, “what is your biggest business problem right now”. This step can take up to 15 minutes and is an eye opening experience. It is also very interesting to hear and learn about other businesses.
3. Once I have clearly identified a problem I can solve, I jump into a demo to show them how Digioh can help.

It’s Also About Honesty

keep calm and be honest

Sometimes in step 2, I discover a few problems that my product can’t solve. This is when I listen, I either refer them to another product or service. This creates goodwill and opens the ability to create a relationship for a future sale. It also makes me look extremely trustworthy and someone that can solve problems.The best sales people are problem solvers!
I would love for you to share your best sales stories in the comments :)

Selling the Dream – Salesforce’s Dreamware


I was speaking to a friend of mine that works at a fortune 500 company. He was telling me how his company is considering adopting a new CRM/ERP system and how Salesforce is very interested in this opportunity. He told me that Salesforce has the most amazing sales presentation. Here is what they do:

Salesforce Sales Process (for Fortune 500 Clients)

  1. Salesforce sales team spends a few days on-site at the clients HQ
  2. Discover any major problems the client has with their existing system
  3. Learn what type of acronyms and buzzwords the client uses
  4. Figure out how Salesforce can solve all their problems
  5. Invite the major decision makers to a “Pitch Meeting”
  6. Present a polished demo of how the client’s company will operate once Salesforce has been fully implemented (they even include the client’s logo inside their Salesforce HQ). The client should feel like all the work is done, and all they have to do is say “Yes!”

Eliminating the “Uggggghhh!!!” reaction

This was one of the most amazing things I have heard. The problem with most software is you always get an “uggghh!!!” reaction from the business owner when selling software, because they know all the headaches required to actually start using it. For example they usually have to get a developer involved, then iron out bugs, and then customize it a little bit for their business.

By eliminating the “Uggghhh!” factor, you get the client excited, and most importantly get to “Yes!” faster. How do you sell the dream – would love any pointers!


How to Close on a Webinar

close-webinars I’ve done a little over 100 webinars and I would like to share a few of my insights if you are just getting started. Here are my three tips to closing customers on your webinar:

1. Tell them exactly what to do to “Upgrade”

When I say exactly, I mean exactly. Here is the script I use:

In order to get all the features I covered today and this incredible deal, just follow my steps: Step 1: Go to this URL {Insert Your Pricing Page URL}

Step 2: Click on the green “Buy” button

Step 3: Enter in your Credit Card Information.

I even show them a screenshot with an arrow of exactly what to do. Then, I repeat the offer and go through the 3 steps again.  I know this sounds pretty unintuitive, but it works! Tell them exactly how to give you money and they will. When I tell webinar attendees exactly what to do to upgrade, I get a 55% conversion rate. When I leave out the exact steps, my conversion rates drop below 15%. Even if the offer and everything in the webinar stays the same.

2. Create a Time Sensitive Irresistible Offer

One of my biggest mistakes was not offering a discount during the webinar. I thought all the information I provided would be more than enough to get them over the edge. If you want your attendees to pay you today, try offering a time-based discount. I usually say something like this:

“This 20% offer is only going to be available during this webinar, after this webinar is over, this discount will be expired.”


I’ve attended a lot of webinars and most of them are BORING snooze fests. Do a webinar, where you can speak LOUDLY, you should be projecting as if you are talking to your grandma and she just lost her hearing aid. Keep things light, fun, and entertaining. Be excited about what you are presenting and your attendees won’t drop off. Here are three things I like to do to pump it up:

1. I like to play Eye of The Tiger before the start of the webinar and I even say “I’m playing my favorite Pump Up song Eye of the Tiger, This should PUMP YOU UP for this amazing webinar we are about to have.”

2. I love what I’m presenting and truly believe in it. Any slides or material that I don’t believe in, I take out immediately.

3. I talk LOUD. My neighbors hate me, but my energy stays high and my webinar attendees love me

What are your webinar secrets? Lets discuss them in the comments below.


Uber … The Partnering Machine


Uber Uber Uber!!! Uber is all the rage these days. They have built an amazing partner marketing machine. I wanted to point out 2 things they are doing that I’m blown away by.

1. Partnership with Google Maps


If you use Google Maps and you have the Uber app installed on your phone. Google Maps will suggest Uber as an option along with the public transit options! This is a pretty big up-sell given that they show you travel times (twice as fast in most cases).

I have no idea how they pulled this off or if there is any money exchange here, but this is some serious prime placement. This is equivalent to going into a grocery store and having your product right next to the cash register.

2. Coupon Codes on Steroids


Every startup is doing the “Get $20 off your first purchase”. This works great, because who doesn’t want free money and startups need to incentive new users to try out their app.


What Uber is doing differently is they are using this strategy with big brands like Lord & Taylor, with major hotels like Hyatt, and big concert venues. This is a pretty amazing strategy, because all those places have customers that need transportation and can afford a cab.

Uber also makes it super easy for you to partner with them. According to their support docs, all you have to do is submit a request here. Well done Uber! Excited to learn more from you.


Everyone loves talking about the growth of their company (total #of downloads, users, etc), but what people should be talking about is active engagement.

  • How many times do you download an app and delete it?
  • How many times do you put in your email on a wait list, but then forget about the service?
  • How many free trial (no credit card required) services do you sign up for and then not use?

You may think you need more customers, but what you really need is more customers using your product regularly.

Here are 3 ways to solve this issue:

  1. Setup an automatic autoresponders (make it look like a personalized email) and figure out why people stop using your app. You have to make sure the first experience gets them exactly what they think your app is suppose to do.
  2. Charge more money. This means that you will have to do more sales up front, but this will get good critical feedback from serious customers only. If you charge money up front, customers will have to take you seriously.
  3. Get the customer committed as soon as possible. Here are three levels of commitment:
    • Lowest: Clicks button (Facebook Connect, Downloads app , etc)
    • Medium: Enters email address
    • Highest: Payment information (credit card details)

Until you get some form of commitment you don’t really have a dedicated user.


My good friend Vishal just asked:

“I don’t know what an automatic autoresponder is….sounds like an automated message to the customer but what does the responder ask?”.

Great question, here is the answer:

What is an auto-responder?

An automatic autoresponder is an automated email you can use to send an email. There are a ton of software companies that can help you do this (in fact it is a billion dollar market). There are high end solutions like ExactTarget and SilverPop that do this ($1k/mo +) and there are also super low end version like AWeber, MailChimp, Infusionsoft, etc ($30/mo +) that can help you do this as well.

Here is what your first autoresponder could look like

Note “FNAME” is the first name of the recipient, it is dynamically added:

Subject: Hey {FNAME}


I saw that you just signed up for our trial. I created the app so if you have any questions, just reply back to this email :)


PS I’m really looking forward to working you!

I like to send this email on a 45 minute time delay from the time they signed up. I also have the email come directly to my inbox if they hit reply. This simple email allows me to learn what the biggest problem with my app or what is confusing them. I can then go back and try to make my app’s first experience super clear.

I also like to send another automatic email after 3 days called “Top 3 FAQ” – this helps address any questions or misconceptions they might have had about the product.



I had no idea how often meetings in the “Real World” would get cancelled or moved. In college you expect meetings to be in stone, mainly because classes and office hours are always on.

Being, 10 years into my professional career I’ve come to terms with meetings getting cancelled and I wanted to share a few of my tips with you.

3 Things to Do When Your Meeting gets Cancelled

  1. People have more important things to do than your meeting. Accept it.
  2. NEVER get mad, this is a way of life! Especially if you asked for the meeting.
  3. Use this email script: “No problem, at all. I totally know how these things can happen. What day/time works for you next week?”. This way you get them to find a time that works for them, the key is to use the word “next week” far enough away for them, and pretty near term for you :)

How to Avoid Cancelled Meetings

  1. Send a calendar invite and ask them to confirm.
  2. Make it a phone call or GoToMeeting unless it has to be in person. If it has to be in-person, you go to their office. People hate traveling for meetings. If it is in-person bring cookies and mention that in the email so people can look forward to something.
  3. Get to the point quickly. Reserve the first 3 minutes to “shoot the shit” and ask how their weekend is but after that get to the point. This will help you get a 2nd meeting.
  4. Make your meetings short. I like sending 15 minute meeting requests, that usually gets more “yes’es” than a full hour.
  5. Don’t assume your meeting is going to get cancelled. If you start doing this, you will get sloppy. Always assume IT’S ON!

What are your meeting tips? I’d love to learn yours!


squatty potty logo

How to sell a ton of Squatty Potty’s:

Step 1: Educate people about something they are doing wrong

Step 2: Provide medical facts

Step 3: Show a low priced product on how you can solve what they are doing wrong. (The word “wrong” is of course a matter of opinion but when you add medical studies and historical evidence the pitch becomes extremely persuasive.)

Check out their convincing educational video and tell me you aren’t convinced:

This reminds me of how the tooth paste become a common household item. They put up billboards saying “lick your teeth” if you feel some grime then you probably need to clean them with some toothpaste.

Phillips, 1942 Commercial:


The next step for SquattyPotty would be to mention that you will smell less making women more attracted to you.

Update (this is awesome, the folks over at SquattyPotty said this):


What are some other good examples of Educational Marketing?


The Rise of Hand Drawn Art

Basecamp homepage-1

Basecamp.com is one of the most copied SaaS landing pages, so when I see a new design on their site, I know it is time to get ready to see more of it. My prediction is we will see a lot more hand drawn art on business websites in the next 6 months. This is a big contrast to the current web design trend on the internet: massive pictures of people smiling and holding a tablet devices in a coffee shop.

People are going to embrace drawn art because it is original, different, and creative. It is also cheaper to create and can convey a simple message in a fun format.

What do you think of using hand drawn art on your landing pages? 

Other Examples of Hand Drawn Art of Landing Pages:


Joe Avella is a long time comedy film maker from Chicago. He asked me if he could write a post on his marketing strategy and I agreed YES right away! I’m a huge fan of Joe and LOL’ed a ton when I saw his new 20 minute webisode of Delivery Dudes. This is a guest blog post by Joe Avella – the writer, director, and creator of Delivery Dudes.

Deliver Dudes Pilot

Leverage My Existing Network

My strategy was to market my new comedy show ‘Delivery Dudes’ only to people connected to the pilot and the show’s existing fans. The production includes 50+ people and had an existing email list of 100 fans. So, I targeted their existing social networks, making the marketing much more focused. Once I’d get those connections, I’d then target the new fan’s networks, and so on and so on.

Playing on friendly connections was a key way to cut through the noise, get a lot of people to connect with the pilot, triple my email list, and get written up on Mashable.com!

What do I want?

I needed a goal before implementing the strategy. I had to decide on one thing I wanted my marketing to do. I’ve found that having multiple goals results in far less impressive results. For me, I wanted email addresses! I feel this is the most important aspect to building a long term fan base.

Building a fanbase on a Facebook page is risky because Facebook can change how pages operate. Twitter is short and fast, so you risk a large percentage of your audience missing your message. With email you can send a message whenever you want and get it the most attention.

First things first

I set up a landing page. My site is hosted by Squarespace, so making a page with the video and an email sign up was super easy. First it had the trailer; later the pilot when it was available. I always included an email sign up form embedded under the video, the form was powered by MailChimp. The goal is to get people to this page with as few clicks as possible and make it easy to give me their email address.

Strategy 1: Facebook Ads

People involved in the production of Delivery Dudes were going to share it, at least I hope they would. Which is great, but to really get the word out I made Facebook Ads, and a few promoted posts. Delivery Dudes starred several actors known among the Chicago improv/comedy scene. A majority of them perform regularly at places like i.O. and Second City. So I targeted the ads to Facebook users who associate with those places.

 Example ads:

I created a few different ads featuring various performers only marketed to people who at least knew of the performer, and in some instances, were already friends.

Ad targeting:

note: picking just the 4 theaters still gave me a target of 340,000 people!

These institutions have several students and performers, and are very tight knit. Users associated with these theaters would recognize the performer in the ad, which greatly increased the click-through rates. The clicks would take them to the landing page which featured the pilot and a chance to join the email list.

Strategy 2: Email Promo Contests

I already had a list going into the release from years of other projects. If you don’t, that’s fine, you can try this once you build yours. I run exclusive content on the email list only and occasionally have giveaways. Leading up to the release I had two separate social media-related giveaways to help get the word out.

#1: Twitter

For one week any member who retweeted this tweet was entered in, with the chance to win a prize from Revolution Brewery.

#2: Instagram

For another week, I asked to share any one of these images on Instagram with the hashtag #DeliveryDudes and you could win a prize from seamless.com. (The giveaways gave fans a higher incentive to share Delivery Dudes with their fan base. A lot of those tweets got retweeted, and several images were liked and ‘regrammed’. (Note: I made the contest as easy as possible. Only one thing to do, and it was easy to do.)

Joe Avella marketing quote-v4

Why do any of this?

In short, it was up to me to get the ball rolling and the word out about the pilot. Sure, some would share it, but after all the work, and the fact that I really believe in this pilot, I wasn’t going to let it get sucked into the eternal nothingness that is the internet.

Running the strategies above forced me to think about how to get people’s attention, target an audience, and obtain something more than a passing glance: the permission for future connection.

Mashable.com coverage

But the biggest impact came from a Mashable writer who saw the pilot on a mutual friend’s FB page. From hustling to get friends of friends to share, one did who was connected to the writer.

Delivery Dudes on Mashable

If I had no game plan, and just threw it out there and ‘hoped for the best’, the incentive to share among those connected, and their potential connections, would be low. It’s safe to assume the pilot would not have gotten very far.

The details of these two strategies can be changed around depending on the project or your goal, but I highly recommend trying something like it. It’s cheap and you never know who’s 1-2 degrees away. Also, please check out my web series delivery dudes and sign up for my mailing list :)


Best Freebie Apps of 2013

George is Cheap

All tools on this list are 100% free! I use all of them daily. I highly recommend them to you too. (Some have paid options for more features, but everything on this list has an amazing free plan)

Genius Scan

Genius Scan

Take a pic on your phone, turn it into a PDF. Boom, done! Perfect for stuff you have to sign. Check it out or tweet it.


Trello To Do List Screen Shot

You can do a million things with it, but I use it as a collaborative To-Do list with my team. Super easy to use on the web and their iPhone app is super slick! Check it out or tweet it.


refresh app screen

Sweet iPhone app that syncs with your LinkedIn, Facebook, and Google Calendar. It sends you a little reminder of your next meeting with information about the person like where they worked, their life milestones, and who you have in common. It helps me “Small Talk”. Check it out or tweet it.


Yes, Skitch made the list again! It is awesome. However, don’t download the newest version. Get the older version. Evernote recently purchased Skitch and made it worse. Check it out or tweet it.


Buffer Screenshot

Schedules your tweets automatically. It helps you not be “That Guy” that takes over your followers newsfeed. Also, an easy way to post updates on multiple social networks at once. I use it to auto-post to my LinkedIn Group and personal Twitter account. Check it out or tweet it.


NewsBlur Screen Shot

Awesome Google Reader replacement. I subscribe to over 300 feeds and their iPhone app rocks too! What is crazy is that I think it is all built by one dude. Check it out or tweet it.


Signals by HubSpot Screen Shot

Email stalking tool. Lets you know if your recipient has opened your email. Works with Gmail and their chrome app rocks da house. This helps me out because I always wonder if they actually read my email. Check it out or tweet it.



After Adobe got broken into, I decided to get on top of my password security. LastPass remembers your passwords for you. This way I can use 11 digit passwords that contain uppers, lowers, numbers, and special characters. Check it out or tweet it.


GAget screen shot

Google Analytics on your iPhone. All I really want to know on a daily basis is how many visitors I got, this little app does it automatically for you with one swipe. Their mac widget is free, but their iPhone app is $2.99. Check it out or tweet it.


Dwolla feature

I’ve been using Dwolla for payroll (perfect for small teams), because it is free (actually $0.25 per transaction) and you can do direct bank deposits. Way cheaper than most payroll solutions which charge monthly fees. Check it out or tweet it.


Team Chat

Awesome private instant messaging tool for my team. Their desktop client works really well. Saves links and images automatically. We use to use Google Chat, but that only allows 1-to-1, hipchat is from team chats. Check it out or tweet it.

Paper Karma

paper karma screen shot

Love this app! It is an “Unsubscribe button” for physical mail. Take a pic of some credit card offer that you get and these guys automatically make sure you never get it again. Check it out or tweet it.



  • Round trip to SFO airport via cab is $120
  • Round trip to SFO airport BART is $18
  • … or I can drive to SFO and park with Flightcar for $FREE! No brainer move here. You can’t beat free airport parking.

Check it out or tweet it.

Alexa chrome plugin

Alexa Internet - Chrome Extension Download

I like to know if the website I’m looking at is a popular one. Alexa’s Chrome plugin does that for me with 1-click. People complain about Alexa’s data being a little off, but it is still a good measure of website popularity. Check it out or tweet it.

What free apps are missing from this list? Let me know in the comments and I will add to this list if it is awesome.


More Free Tool Suggestions from the comments!

Dharmesh’s Suggestions:

  • Flowdock – What Google Wave should have been, chat + Inbox for teams

Nitin’s Suggestions:

  • Asana – Project Management Tool
  • awesome screenshots – Chrome plugin for taking screen shots
  • Pandora – Awesome app for music radio, suggests new music based on your listening habits
  • Mint – AMAZING personal finance app, put in all your bank and credit card accounts and it automatically categorizes your finances, I love the budgeting feature because it lets you know when you are spending more in a certain area.
  • Apple Podcasts – podcast app 

Anand’s Suggestions:

  • RescueTime – shows you how you spend time your time on the web.