Hack & Hustle

Sales Mindset: Attached & Fearful Vs. Committed & Couragous

We share a lot of sales tactics for very specific situations you encounter when you're trying to drum up business on our blog. But I believe that some of the biggest gains you can get are not by learning tactics, but by shifting your mindset. That's of course also the harder thing to do, but that shouldn't deter you.

One common reason why founders fail to sell as good as they actually could is that they are attached and fearful, when they should really be committed and courageous.

  • Why feeling that "your business is your baby" can be a bad thing.
  • How being attached to outcomes can sabotage your sales success.
  • When letting your business endeveaours fail can actually be a catalyst for growth
  • Feel a little timid and fearful? Have a hard time selling your product or service? There's a way to rethink the way you think about your business that can lead to much better results.
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The Real Reason Why Y Combinator Is Dominating The World Of Startups!

I recently talked with a guy who's about to launch an incubator in Europe, and he asked me about my experiences at Y Combinator. He wanted to know what makes Y Combinator the arguably most successful incubator there is.

Is it Paul Graham's genius? Is it the amazing partners?  The awesome network? Is it the quality of the founders and partners? The way the program is set up?

All of these things are major elements of Y Combinator's success, but my personal interpretation of what really makes YC the number one player in this game is something else...


When Thomas, Anthony and I got into YC, there were two things that impressed me a lot on the first day of the program.

"You're one of us."

Paul Graham welcomed everyone and said basically: "Guys, you're now all part of Y Combinator. There's nothing that you can do or say or screw up so badly that we'll change our minds. If something dramatically bad happens, come to us first - that's why we're here. We're there for you when things go down. And believe us. No matter how catastrophic things seem to you, we've seen this before. There's no way we're going to turn our backs to you, you're now part of the family."

That's a very empowering thing to hear as an entrepreneur. It gives you the freedom to stop trying to impress the YC crew, and you don't have to invest your energy into trying to hide your flaws and failures.

The Circle of Trust

At YC there's a tradition of Tuesday Dinners, where some very accomplished person comes to YC and talks about their experiences and shares their insights with the YC alumni. People like Mark Zuckerberg, Mark Andreessen... really high-caliber investors. These aren't the typical speeches you get to hear at conferences - they really let their guard down and "share it as it is". No publicity-versions of real events.

There's a rule about these talks: everything that happens at Tuesday Dinners stays at Tuesday Dinners. No tweeting about it, no blogging or other forms of sharing it. They can afford to actually share unfiltered insights and raw opinions they wouldn't share publicly. And there's a lot of value in that kind of shocking honesty shared by entrepreneurs who seem to have it all figured out. 

Why do they share it with what's basically a bunch of strangers to them? Because they know the Y Combinator network is trustworthy.

Don't be the founder that fucks it up for everyone else

And then PG said: "We've been able to maintain this circle of trust for many years. That's why these people come here again and again and share stories they never tell anyone else. And the only reason why they keep doing that is because they can trust us. Don't be the founder that ruins this for everyone else forever. Don't be the first person who breaks that trust and destroys the value."

The room went very silent. You could feel the tension - because we've all been entrusted with a heavy responsibility. Nobody wanted to be the person that fucks it up for everyone else.

We all shared these secrets, and it forged a strong bond among the group of new alumni sitting in the room.

It goes back to something I've spoken about before: trust trumps everything.

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How to respond to an RFI?

Have you received an RFI (Request For Information) from a large organization or government agency? This could turn into a huge deal - but there's a lot of complexity involved.

What's the best way to respond to an RFI?

First of all, the appropriate response to an RFI is this:

Keep It Simple

Way too many people freak out when they receive an RFI. They see this huge opportunity, and their mind goes into hyperdrive - full speed in the wrong direction.

They spend hours and hours studying about the RFI process, about the company that requested it, about the person in charge, about potential competitors and on and on. They discuss it with their team members and ask smart people for advice. They learn about procurement procedures, contract vehicles

Their mind drowns in a sea of questions, for which they try to come up with the answers in their own mind. They make all kinds of assumptions, they worry, they get caught up in their own head.

When you're getting caught up in a net of complexity, seek simplicity.

How exactly do you 'seek simplicity' when you received an RFI?

Pick Up The Phone And Call Them!

Look at the RFI letter you received. Do you see a phone number somewhere? Pick up the phone and dial that number.

Say this: "Hey John, I just got your RFI. Really awesome that you guys included us. I need five minutes of your time to ask a few follow up questions, and make sure that we can make a good decision if we want to be part of this or not."

That's it. A few simple, but important questions.

What Should You Ask them?

Ask them a couple of big picture questions. At this point it's really just about figuring out whether it's worth your time to actually put together and submit a response, or whether it would be a waste of time for you. 

  • How did you find us?
  • Why did you decide to include us in the process?
  • How many other vendors are in the process?
  • Do you have examples of winning bids in the past that could guide us in terms of what the most successful way is to give you the information you need?
  • Is there one of the participants that you guys have been further in the discussion with than others?
  • You said that there's ten things that are really important to you. Can we go through them really quickly, and can you give me some context on why these things are important?

The answers to these questions provide the context you need to make an informed decision. Can you win this deal? Is it a good fit? If yes, how exactly do you need to provide the information to the prospect? How do you have to play this game to win? 

But won't asking these questions make me seem amateurish?

Many founders and small business owners are intimidated by prospective government agencies and large organizations. They're concerned to blow it by revealing their lack of knowledge, not speaking the right lingo, or not knowing what to do.

The important thing to keep in mind is: you're not asking them to hold your hand while writing the RFI. You're asking them legitimate questions to assess 

What If You Can't Call Them?

Sometimes you can't reach the right person by phone, or the person in charge isn't willing to talk with you. In that case, send them an email.

The important thing is to respond quickly. It's an opportunity to show them you're responsive and professional. It's an opportunity to demonstrate you're the kind of vendor they'll enjoy dealing with.

Is It Worth It To Work It?

There's no hack to simplify the complex buying process of a large organization or a government agency to a point where it can all be explained in one blog post. (Although you should definitely shorten the buying cycle by using the "previous contract hack"!) 

Responding properly to an RFI takes time - it's not enough to just send them marketing materials. You'll need to put together a customized package that succinctly tells the buyer what they'd get from you, and answer their questions in a way that will make your response stand out from all the other vendors.

But before you go down that road, quickly find out whether it'll be worth your time. If there's a real opportunity for you to close a major deal, then it might be worth to put in the effort.

But don't understimate this. Selling to large organizations is a significant investment of your company's resources. Long sales cycles with uncertain outcome can kill startups or small businesses.

Chasing the wrong rabbit just because they sent you an RFI can be a costly distraction. Simply asking the right questions will help you to keep your focus.

Further Reading on RFIs by Others:

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Week of bug fixes

We spent this week looking through a backlog of bugs and fixing as many of them as possible. Here's the update.

  • Fixed a bug where merging leads would sometimes result in showing duplicate emails in the resulting merged lead.
  • Fixed a bug where duplicate emails could be sent under certain conditions.
  • Fixed an issue where replies sent from Close.io sometimes wouldn't be associated with the original email.
  • When changing your SMTP credentials, try to resend any emails stuck in "outbox" immediately.
  • Emails that didn't have a "from name" associated with them would incorrectly show the currently logged in Close.io user's name as the "from name". This is now fixed.
  • Fixed the edit lead form so the "URL" field isn't marked red/incorrect if you enter a URL without "http://", since we auto-prefix with http:// for you.
  • Fixes to Explorer that prevented certain combinations of filters from working.
  • Fixed a JavaScript error caused when switching organizations after viewing Customizations settings page.
  • Fixed a bug where creating a lead/opportunity status with an existing name would fail, but without showing a reason.
  • Added support for abbreviations of Puerto Rico, US Virgin Islands, and US Armed Forces in an address "state" field.
  • Answering a call on your phone number from a different organization now switches you into the relevent organization.
  • Fixed expanding and editing of contact details on touch devices like iPad.
  • Enabled clicking on a Smart View link for a page you're already on to reload the search results.
  • Fixed a bug where thousand separators and currency codes would be included in the CSV exporter, making Excel not recognize the cells as numeric.

Plus, added a couple features, for good measure:

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Introducing Explorer: customizable reporting graphs

You've been asking for more advanced ways to report on your sales data inside Close.io – summary information about your leads, opportunities, calls, emails, etc. Rather than just adding another report inside Close.io to answer a couple common questions, we've put together a data exploration tool to help you visualize your data, in graph form, in hundreds of new and useful ways. We call it Explorer.

Explorer lets you quickly create line graphs and bar charts based on whichever parts of your sales data you care about. You choose a metric for the vertical y-axis, a field for the horizontal x-axis, and any applicable filters, and we'll bring you a graph in seconds. 


Here are just some of the questions that Explorer can now help answer:


  • Show me a breakdown of my leads by a specific text custom field (e.g. Industry).
  • What % of my leads have a specific numerical custom field value (e.g. Score)?
  • Show me a line graph of how many leads have a certain date custom field value (e.g. Contract Ends Date).
  • Show me my how many of my leads were created by each teammate.
  • Show me when leads in a specific Smart View were created (how many per week/month).
  • How many points of contact do we have per company, on average?
  • Show me the breakdown of all my leads bucketed by how many times I've communicated with them.
  • For a specific lead status, show me how long ago our latest communication was with those leads.
  • I'd like to know if our first point of communication with current customers was more often a call vs. email.
  • How many of our leads still need phone numbers or an address added to them?
  • Show a breakdown of leads created manually, by API, or by email.
  • Do we communicate, on average, more with certain types of customers/leads than others?

Opportunities & Opportunity Value

  • Show me a graph of $ in closed deals, over time, by user.
  • Show me how many opportunities were created by each sales person, over time.
  • Show me how many total active/won/lost opportunities each teammate created.
  • Show opportunities broken out in buckets of their deal size.
  • Show me a graph of how many opportunities were won over time, and when.
  • Show me how many leads have more than one Active opportunity.

Duration of Calls

  • Are we making more minutes in sales calls per day/week/month than we used to?
  • How do our incoming call's vs. outgoing call's durations compare?
  • Show me the average call duration, per sales person, over time.
  • Are our sales calls longer, on average, at certain times in a day?
  • Have our sales calls gotten longer or shorter over time?
  • What percentage of our calls are over 1 minute in length?
  • Are calls to leads in one Smart View longer or shorter than calls made to another?

Number of Calls

  • Are we making more calls per day/week/month than we used to?
  • Show me how the number of calls compares between sales people.
  • For leads in a specific Smart View, show me how many calls were made over time, and by whom.
  • Are the number of calls over 1 minute in length higher on certain days of the week?
  • Do we make more calls with our current customers, or with prospects? 
  • What percentage of our leads have never been called? Called more than once?


  • How many emails were sent, over time, by person?
  • Which % of my emails are opened? Opened more than once?
  • Show me how many emails from a specific Smart View were replied to.
  • Which email templates are our team using most often?
  • Are we getting more incoming emails than we used to?

... and many more.

Learn more about Explorer on our FAQ page.

Explorer has been live in Close.io since last Friday – check it out under Reporting -> Explorer! It's free for all Close.io users until October 1, and then it will live inside our Business plan. 

We expect Explorer to get better over time. Please share with us which graphs you find particularly useful, and other other feedback about the new feature.

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What Can Legit Startups Learn From Shady MLM Businesses?

Think of Multi-Level Marketing (MLM) what you want - there's one thing we founders and sales reps can learn from these people. 



We all know that these MLM schemes are bullshit. What they're pitching you is too good to be true. You know it.

But a really skilled MLM sales rep will be able to have that little voice in the back of your mind ask you: "... but what if this is true? What if I'm missing out? What if this is the one exception to the rule?"

All successful MLM businesses do one thing masterfully: building credibility.


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Call Forwarding UI

Quick update --

You can now edit your call forwarding number and turn on/off forwarding quickly from within your Close.io settings.

Head to Settings -> Phone Settings -> Call Forwarding to checkout the new section:


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How NOT To Be Frustrated By Failure: Don't Celebrate Your Losses

Here’s a little happiness hack for entrepreneurs: don’t celebrate your failures. You’ve probably already heard you should celebrate your successes, to make sure you and your team cherish and enjoy your victories.

I think that’s great advice… in theory. I just find it hard to practice. I’ve been an entrepreneur all my life, and I’ve had my fair share of successes and failures, ups and downs.

And the one thing that stayed consistent through all of it was this: failure hurts much more than success delights.

It turns out I’m not the only one who’s wired this way. Many entrepreneurs I speak with can relate to this phenomenon.

The Negativity Bias

It’s a universal human characteristic: Bad is stronger than good. That’s the gist of a study Roy F. Baumeister popularized.

  • Daniel Kahneman and Amos Tversky found that losing $50 is much more upsetting than it is pleasing to gain $50 - this is what the loss-aversion theory is about. We value gains and losses differently.

  • Researchers also found that having a bad day often had a negative impact on the following day, whereas having a good day did not carry over to the following day. Even if the bad and the good are experienced with equal intensity - people tend to carry only the bad over to the next day, and let go off the good.

  • Another study found that we react more intensely to bad odors than to pleasant odors. Just try walking past a garbage truck and smelling a flower or freshly baked cookies. You prefer the latter one, but the first one affects you so much more.


Why Do We Focus On The Negative By Default?

It seems our brains are wired this way. Negative experiences get processed by our implicit (emotional) memory almost instantly. Positive experiences on the other hand take about 5 to 20 seconds to begin to register in implicit memory.

Look at it from an evolutionary point of view. People who are “more attuned to bad things would have been more likely to survive threats and, consequently, would have increased the probability of passing along their genes,” said Roy Baumeister in an article “Survival requires urgent attention to possible bad outcomes but less urgent with regard to good ones.”

5 Against 1

If you just let your brain do what it’s used to do, and you’re just like most people, there’s an unfair fight going on in your mind. Baumeister’s research shows that it takes on average 5 positive experiences to balance out the impact of one negative experience.

The Good News: You’re In Charge

Fortunately, knowing this, you can use your mind in a way that makes you happier, and lessens the impact of negative events. You have a say in what your brain pays attention to - you're not a passive recipient of the feelings your brain hands you. 

And that’s exactly what this happiness hack is about. 

Thinking ‘I Should Feel Happier’ Didn’t Make Me Feel Happier

When I didn’t celebrate my successes as much as I thought I should, and then tried to force myself into being happier about it, it almost had the opposite effect. Rather than making me happier, it took away from the little joy I got out of it. I felt like I failed at being happy about it, and even experienced a pinch of guilt.

Given that amplifying the joy of success proved difficult - how about doing something else, instead of just trying harder?

Could I turn the “emotional volume” of failure down when some part of our operation didn't move the vision for our inside sales CRM forward?


Could I train myself to care less about failure, not be so affected by it?

Turns out this worked a lot better.

It’s easy for me to tell myself after a period of bad results.

If you ever catch yourself getting frustrated with failure, just tell yourself this:

It’ll pass, another week will come, another month will come. Let’s not get all worked up about this problem, let’s just solve it and move on. If I don’t celebrate my successes, I’m not going to celebrate my failures.

Like a Buddhist monk, you can let go of these negative feelings the moment you become aware of them. Watch them disappear in the distance, get washed away by the rain. (It's much better to use your imagination for positive purposes than to imagine how everyone will hate you because you didn't perform).

There’s no point in punishing yourself with bad feelings when you failed to perform. Nobody gains from that. Burning your emotional energy on frustration is a waste - it takes away from the focus and energy you need to move forward, find creative solutions and grow your business.

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B2B Sales: The 3 Levels Of Customer Needs

Here’s one of the most common mistakes I see startups committing when doing B2B sales. They assume that selling to businesses literally means selling to businesses. It doesn’t. Selling to businesses is multidimensional. You’re selling to:

  1. The company
  2. The department
  3. The individual person


In an ideal world you’d focus on selling on all three levels. In the real world (where you’re operating with limited time and resources) you’ll often have to prioritise.

What do you think, which is the most important level to sell on?

When you’re qualifying the needs of the buyer, whose needs exactly are you eliciting? Do you learn about the company’s needs? The department’s needs? The individual’s needs?

Let’s look at those three in more detail.

The Company Level

These are the needs of the company you’re selling to. Here are some typical examples of company needs:

  • big strategic initiatives

  • launching a new product or major feature

  • total revenue numbers

  • cost savings

  • large-scale marketing and brand campaigns

  • competitive game plan

  • etc

The Department Level

These are the needs of the specific department you’re selling into. Among these needs are:

  • specific KPIs that the department is measured against

  • projects the department has to complete

  • strategic initiatives this department has to see through

  • company politics (e.g. company internal “wars” with other departments, competition for budgets & resources, internal power struggles, etc)

  • potential changes in management of that department

  • desire to solve particular problems the department is charged with

  • circumnavigating externally imposed constraints

  • etc

The Individual Level

These are the needs of the actual decision maker - or the internal champion who will “help” the decision maker to make the right choice. Among the needs of this person are often:

  • personal career goals like getting promoted, getting a raise, securing their position, etc

  • deliverables that person wants to be credited for

  • personal life goals

  • family goals (e.g. wanting to spend more time with the family, moving elsewhere, providing kids with better education, spending less time with the family

  • getting hired for another company

  • etc

I recently talked about this with Gary Vaynerchuk:

You can watch the whole segment of the interview on B2B sales here.

There’s a great story on the importance of individual buyer needs when selling to large organizations in Ben Horowitz’ book The Hard Thing About Hard Things:


In this case, they ended up buying a whole company just to meet one of Franks needs. If you haven’t read the book yet, I definitely recommend you do so now.

How To Deal With Conflicting Needs

Sometimes the needs of the individual buyer are aligned with the company and department level needs, but many times they are not. Many times what the company wants and what the individual buyer wants is in conflict with each other. What do you do in a situation like this?

If your product/service actually provides massive value to the company, then by all means do give the individual buyer what they need to make the decision in your favor.

Let’s say the buyer wants to get a job at another company. If he’s a talented employee, that’s obviously not in the interest of the purchasing company. If the overall value you deliver outweighs the downside, you should still make it happen.

Again, Gary put it clearly:

If you’ve got a good steak, make the spark and the sizzle whatever it needs to be.

Focus On The Individual Needs First and Foremost

When you’re selling, adjust your value proposition so that it fits the individual’s needs best. It’s harder to do this, because you need to establish some real rapport.

You have to get the person to open up, which requires a deeper-level conversation than talking just about company needs - but that’s exactly why so few people do it, and why it will give you an advantage over other vendors.

Have a question or comment? Tweet at me! :)

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Sales Objection: "It's Not a Priority Right Now"

You've had a great sales conversation with a prospect, pitched your product, asked for the close... and your prospective buyer tells you: "This sounds all really good, but it's just not a priority for us right now."

How do you respond to that? What can you do to make a sale happen?

There are two ways of handling the "this just isn't a priority right now"-objection. Which of the two you should choose depends on why the prospect tells you it's not a priority.

Reason #1: Your Pitch Doesn't Push Their Buttons

Did you properly qualify your prospects? Do you really understand their needs, challenges and priorities? 

If not, you need to ask more questions until you have a clear picture of what matters to them.

Then you can customize your sales pitch to match their priorities.

If you're going to use a generic, one-size fits all value proposition, you're going to miss out on a lot of opportunities. One of the reasons why sales people can create more revenue is precisely because they can personalize the sales approach for each prospect.


The same product/service can be presented in different ways, to match different needs.

Example: Saving Costs vs Increasing Revenue

Let's say your solution helps businesses to reduce their accounting costs, and for a particular prospect you estimate it could save them $20,000. After qualifying your prospect, you learn all they care about is increasing revenue though. 

What do you do? Just pitch them on saving $20k on accounting? Hope that they'll bite, because, well, a dollar saved is a dollar earned?


You get creative and present your solution as a way to increase revenue. This will require further questioning. And you make it about identifying opportunities how $20k can be put to use to increase revenues.

Don't expect the prospect to connect the dots - it's your job as a sales person to find ways to create value for them. Sales isn't just about peddling your goods - it's about consulting them to better achieve their goals.

Reason #2: They're Avoiding the Real Issue

You have qualified them and they told you about their priorities. You adjusted your pitch to match these priorities. But when you ask for the close, they tell you: "This sounds all good, but it's just not really a priority now."

What's going on? Maybe you misunderstood them, maybe they just bullshitted you about their priorities.

There's some kind of disconnect - but what do you do about it?

How do you get to the real issue?

You just ask them: "You know what? I'm struggling with this, and I need your help. How come that it's not a priority, since you mentioned that increasing revenue in the next quarter or two is really the number one goal that you guys have in mind? And I think I've demonstrated that our product could help you accomplish that in a pretty powerful way. Where is the disconnect? What am I missing? Why isn't this a priority at this point?"

Don't be confrontational about it - just be upfront and honest, and ask them to resolve this mismatch in a way that allows them to save face.


Oftentimes they just told you a little white lie because they were polite, or they were just uncomfortable to bring up the real issue. At this point, many inexperienced sales people make it about who is right and who is wrong. Yes, you can start to argue with them and prove them wrong, point out their fallacies. But do you want to close the deal or do you want to be right?

Most of the time if you probe, the prospect will then tell you about the real objection, for example:

  • "You know, it actually is a high priority right now, but the thing is, we've tried this many times with other startups, and one issue we had is the technology looks really cool, but it's usually not mature, and then it takes way longer to implement than we thought, so, I really don't want to get into these problems." → It's really about a lack of trust!
  • "You know what, the disconnect is that I don't really think you're going to move the needle on the revenue side. Yes, this could bring like a 2% improvement, but we're looking for 30% growth! And we already plan to do X, Y and Z to increase our revenue. This is really a small distraction, its not going to make a big enough difference." → It's about your value proposition.

NOW you have something you can work with. Here's a real objection you can manage to move the sale forward!

In sales, an inconvenient truth is always better than a convenient lie.

Because it's something you can use to move the deal forward (or determine this just isn't a fit and stop wasting your time on a bad prospect).

If they still give you "not a priority BS", become more confrontational.

Challenge them.

Ask them: "What would need to happen to make this a priority? If you're three quarters into the year and you're not on track to meet revenue goals, and you don't have more budget to spend? If you fail to grow revenues and your company needs to let people be able to afford more for marketing - will it then be a priority?"

You'll want to get a good sense for who you're dealing with before you take the gloves off, but sometimes that's what it takes.

The thing is, "not really a priority" should never be the reason why they resist your pitch - if you've properly qualified them and identified them as a good fit.

"It's not really a priority" should never be the final argument in a sales conversation.

There's always a next step - it might ultimately lead to figuring out that they're actually not a good fit, but oftentimes you'll see that there's an undiscovered opportunity to create a win-win.

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