Learning to Sell … Art of Reading the Deal

I was really lucky coming out of college to get hired by Burroughs Corporation  which was a leader in mainframe computing platforms and a Fortune 50 company (later Burroughs merged with Sperry to create Unisys).  At the time most big companies had management training programs that took 50 new hires from around the country and trained them on technology, business, and the art of selling.  They generally picked people that had good technical acumen but as I learned later what they were really looking for were extroverted people that had good people/listening skills which they could train on the market vs. hiring tech people and teaching them “softer” skills.   I was fortunate enough to be one of those “Good Athlete” hires!

We spent a year in and out of the classroom setting and traveled to sites all over the country.  I’ve often called it my MBA.  I learned about technology, various vertical markets,  the art and science of selling and even how to dress for success (with a trip to the Malvern PA mall with an instructor showing the class the best shoes to buy!) … but most of all I learned to SELL and CLOSE deals by working alongside some of the best professional sales guys I’ve ever met!

One life lesson I really took away was that evaluating and strategesing an opportunity is more art than science.  Anyone can read a book on selling or travel with a sales guy on a single trip and say “I can do that”, however, I learned that selling is being able to quickly understand an organization, adopting the tone and tenor of your customer, and being able to read the tea leaves in how best to provide the information your customer/prospect needs to make a decision. It is a softer skill.  Sure you need metrics and strong pipelines to be successful but each deal on its own requires finesse and takes on a life of its own.

Some of the lessons I learned early on in my career I still use today or think about when I’m working with customers, coaching my sales teams, or reviewing forecasts and pipelines. Oh … and I still make sure my shoes are polished and tie hits right at the belt buckle if I’m going to more formal meetings!

Lesson 1 — Art of Reading the Deal:

I was in my second or third year and was running a territory in New England selling to some of the largest banks and financial institutions.  I’d made Presidents Club and was feeling pretty good about myself (yes, sales people are cocky!).  I was assigned Liberty Mutual Insurance as a new account and quickly found a pretty big deal for PC’s and a network.  Of course I forecast it and started spending a ton of time working with the customer.

Sitting adjacent to me was a chain smoking older sales guy in a completely different territory.  He pulled me into a conference room and asked me a few very basic questions on the people at the account, drivers for the projects, and budget.  After 3-5 minutes he gruffly said “walk away kid you’ll never win”.  Well I hated him after that.  What did he know, he hadn’t even met the account and weren’t we taught to keep fighting and figuring out how to close anyway?

Well guess what … I lost the deal after several months of effort and EVERYTHING Bob told me would happen … DID HAPPEN.  Following that loss I learned how to take in the smallest details , listen better, and apply what I learned in past projects to the one I was currently on. I even learned to walkaway (although I hate that still!)

Now 15+ years later I find the I can now look at a sales situation and use the experiences I’ve had working with customers and think back to a similar situation and pull out the playbook.  I’ve found that most situations have some theme to draw from regardless of market, product, or issue.  Selling is selling … buying is buying!

It’s kind of like a movie — if you know its a romantic comedy you can usually figure out the general plot and with fairly good accuracy figure out the ending by reading the subtle twists that are generally standard for stories of that genre. Sure the names change and locations are different but if you’ve seen enough movies you know the story line and general plot twists.

Selling is just like that.  If you know how to read people, listen, communicate, quarterback resources efficiently, negotiate, close, and support you can do it across products, markets, and industries. It becomes intuitive.

In selling — Listen, Be Nimble, Listen, Be Humble, Listen … AND TRUST YOUR INSTINCTS!


Where have you been ?

Good Question!

As you can see I have not blogged in a long time.  Not because I’ve not had a desire but because I’ve been busy with a robotics start-up over the last 18 months.  During this period I’ve learned a lot about starting a business since the financial market melt down and working with savvy entrepreneurs.

In forthcoming posts I’d like to continue to find my voice as an advocate for “customer development” which I’m afraid still very much gets shuffled to the background by way to many VC’s, startups, and even at times … sales and marketing personnel!

If you read this blog … please encourage me to post and to provide real examples of the great, good, and even ugly examples of how companies are going about understanding new markets, getting “bottom’s up” customer feedback, acting on that data, and closing real business.

Oh and since this sounded way to formal I’ll also try and post on stories relating to other passions including sports, music, and family.

Decision Making … It says alot about people and companies

I’ve worked with lots of people and companies over my career and I’m constantly amazed by how the culture of various teams can be determined simply based on how they make decisions and treat people/vendors.  These decisions can take a number of forms including how they buy products, fund companies, and even how they hire people. Recognizing the different styles quickly is easy and can certainly save a lot of valuable time!

In thinking about this recently I’ve realized people (and by association their company) can fall into several high level categories:


  • Provide clear direction on what they are looking for, steps/deadlines, and provide feedback as you go thru the process in timely manner
  • Often get to salient differentiators quickly and leverage practical experience to guide their thoughts
  • They give quick yes/no answers and tell you why they are going in a particular direction … even if not with you or your product.
  • Their rationale for the decision passes the “sniff test” and you feel they paid attention to your ideas in appropriate manner.

Recently I’ve been raising money for a startup I’m heavily involved with.  We have seen a number of VC’s and mostly all have fallen into this bucket.  One in particular, however, stands out as a great example.  I’ll keep the name private for the moment — but you might figure out who it is.  I pitched him a few years ago when he was with another firm in the area for a different company I was with and about 20 minutes into the 1 hour meeting he said “guys I’m gonna pass … and here is why”.  At first it was a little difficult to take the feedback (and quick no) but upon reflection it was spot on and it allowed us to move on to more relevant targets (we eventually closed a round with more appropriate VCs).    This partner has now moved on to his own shop and I reached out a few weeks ago to see his interest in this new project. He quickly responded to email dialogs and set the meeting up in an appropriate window given calendars.  After our first meeting went 30 minutes over allocated time we had clear next steps, got clear feedback as we went along, calls returned promptly … and then a prompt NO!

OK … so the story didn’t have a happy ending — but regardless I still really liked the process, have a good feeling for the VC, gained insight on what he didn’t like/had issues with and we can continue on in funding process.

These types of people/companies are winners!  You may not always agree with the output but bet your money here and you will win!


  • Want lots of analytical data and deep details (sometimes more than any others have asked for)
  • Involve many people in the process
  • Make decisions based on matrix comparison and after thorough technical research
  • Takes a longer time to plan but execution is usually on target to goal dates
  • Once they make a decision it is bought in from top to bottom and execution commences immediately

This style is often driven from the top of the organization and can really work well … if used appropriately (i.e. does not get too bogged down in irrelevant analytical detail and BS).  At a company I was with for much of the ’90s we DID NOT follow this decision making process and it was reflected in the well known culture of the company.  Sure we got things done fast — but often at a longer term cost. In contrast at my first startup we did spend a lot of time planning, looking at strategic implications and for the most part made decisions in a quick and clearly communicated fashion.  The success of that company and the market reputation we developed I can clearly equate to the decision process we utilized.

On the sales side of dealing with these companies you have a longer process than “from the gut” people — but as long as communication stays open these can often be the most rewarding wins and long term relationships.

While these companies/people are methodical and slower moving they are not likely to be down for long in tough markets and assuming they don’t trip over the curb stone the longer term horizon is likely well seen.  The trick here is to balance strategy and tactics!


  • Say they move fast … but they don’t and decisions drag for evvvvvver
  • Say they are consensus driven … but they are not
  • Say the will give honest feedback … but it is not provided
  • Say they are going to be a great company … but it can’t be!

OK — this is pretty obvious and there are unfortunately too many of these types of companies, investors, and people out there right now.  The challenge is figuring out how to identify them so you don’t waste precious sales resources or personal time chasing them for funds, sales, or a job.

In running sales at my last company we called on a few of these types of companies.  They ended up wasting a lot of our time, ate up travel budgets, gave us false hopes and it took a lot of effort to get the internal team to walk away (which we correctly did before it became a larger problem). Oh and the one company I’m thinking about in particular is now in Chapter 11.

I admit its hard to walk away from a perspective customer who say’s all the right stuff about project funding, meets with you, returns calls every so often … but can never say no!

Its hard too to not go after a VC who you is with a firm that all indications are they are not doing investments or running out of money … but still meet with you!

Walking away from a potential job because the interview/recruiting process and company culture feels “Dysfunctional” is also hard but think about it … if they can’t make a decision during a RECRUITING process what will life be like as an employee!

I’m sure there are many other subsets of these types of companies and great examples but I’ve experienced all three of these distinct types in the last week or so and just couldn’t let it go without a comment.

Raising Money — view from the other side

I’ve been involved with raising money for 5 different start-ups and without going back thru every business card I guess I’ve pitched about 75+ different firms and likely a lot more.  If I include the websites I’ve visited and research I did on firms I did not contact I’ve likely looked at or discussed >300 firms.  Depending on your perspective that’s either a lot or not very many!  For everyone of these raises I found that it took considerable effort to distill 100’s of data points, references, market trends, etc into the 15 or so that got the points across crisply and showed the compelling value of the idea/company.

Currently I’m helping three different teams raise money each in a unique market (Cloud Storage, Robotics, and Alt Energy) but all with the same challenges.  What I find amazing (and I guess refreshing for someone like me) is how similar the needs are between each company seeking to raise the funds and how with a really open team you can quickly see the problem in telling the story and embark on fixing it.  Honestly you do not have to be a domain expert you just have to listen well and apply common lessons from past experiences and the answers/ideas start to flow.

To understand what I’m talking about first lets look at VC traits as to craft a story you have to know your audience.  As a general rule VC’s are:

  • Outgoing, personable, generally willing to listen, Type A … BUT
  • Short attention span … if you don’t figure out and diffuse their major objection is likely to be within opening minutes your toast (more on that later)
  • Feedback is weak and not often helpful as they don’t want to appear rude (“that idea just sucks”), want to preserve relationship, can’t share partner/firm dynamics and lastly don’t want to deal with time consuming counter arguments
  • They often DO know more about the markets than they let on AND the competition you are going to face in coming years — but you have to listen carefully for signals in their questions to gain from that insight.
  • Lastly they look at on average a deal or two a day at some level … they only do a few a year so pretty easy to say no to you if any hair raises on their neck!

So with all that against raising money and communicating your idea here are a few of the simple steps I follow when embarking on the process:

  1. Develop a crisp story and refine constantly
  2. Create a targeted and phased VC approach list and track progress/follow-up crisply
  3. Have your customer & market references ready to go for 2nd level questions/diligence in various forms to meet different styles
  4. Bring the right pitch team to meetings
  5. Follow-up for feedback appropriately and with expectations in right place
  6. Never lie and ALWAYS admit problems, concerns, communicate openly
  7. Once they say no … it over.  REALLY
  8. Don’t get discouraged

Lets quickly jump into each of the above area so I can explain further what I’m talking about because this list is pretty obvious — but here is the point … I’m amazed by how few people really do it!


There are great posts on what should be in a Exec Summary or VC pitch — HERE & HERE so I’m not going to cover that part.  What I’m going to comment on is the mechanics and mistakes I’ve seen.  First figure out what the likely objection is and bring it to the front on the deck.  For example if you think that VC’s may not know a lot about your end market or growth prospects get that on the table before you explain the solution.  If concerns are competitive in nature bring the competition slide right up front and say why you are different before you show product ideas.

What this does is kills the tendency we all have to listen to a pitch and decide why the idea won’t work. By eliminating the common objectives first people sit back and listen in a more appropriate frame of mind. I’ve even gotten up and verbally said “here are the three things you are likely concerned about X,Y, Z because we have heard this from others. Well in this presentation we are going to tell you why these concerns are unfounded and how we  have the ability to kick Big Guy Named Competitor, do have a unique go to market approach, and have the following four customers behind our idea and will leave you with an MP3 of their testimonials on the way out”.

Another tendency I’ve seen is to try and do too much in the first meeting and put too much information out.  My favorite technique to resolve which my CEO at Sitera taught me is to lay out all the slides on the conference room table and look at it from above.  You can really then see redundant information, which slides are too wordy and can go to pictures, and re-order your points in rapid fashion.

Last point on story development is time allocation.  It will take you 6-8 weeks before you are really ready to go and plan too to regularly schedule time once active to modify your existing approach and story.  Yes, that sounds like a lot of time and you can have draft decks for “friends of the company” before that period but remember it takes time to get crisp data and good at telling the story.  Don’t rush it and constantly rethink, change, dump slides/ideas you worked days on and question “will they get it”.  Remember you get one hour max on first meeting and they are not being dumb in not getting it (yes, I had someone say that to me once) it is your story they can’t get!


Putting together a real approach strategy is critical.  It’s just like a sales pipeline you have to know who to target, understand the funnel, track responses and actions, and know when it is appropriate to ask for the order.

I like to break my approach list into these categories and approach the meetings as follows:

  • “Friend of Mine/Company” — Tell them upfront you are pitching them first and only looking for feedback and issues.  Don’t expect investment.  You know partner very well and they know it is practice.  Pick 2-3 guys to talk to.  Keep it casual.
  • “Initial Targets” — Local to your company, mid-size firms, domain knowledge with history of investing in your space and stage.  Pick 4-6 guys to target and then refine pitch.  This is not Madison Square Garden — but these guys are real so do it right. Odds are 1 may stay active .. but that’s OK its a big ocean.
  • “A List” — OK now you are ready.  Hit the big guys.  The ones who are very active.  Pull out all the stops to get meetings.  I’d still stick with an approach list of about 10 and realize that will take about 30 days to really hit and schedule. So reality you will have two waves to refine your pitch.

OK … now the dilemma.  If you do it right life is good.  No further early pitches as you have enough action to feel like you are going deeper into DD with at least three firms.  However, life is never that good.  What to do next?

I always keep my list of “B’s” and “C’s”.  If my my meeting pipeline is looking bare I go to the next group on the list. I may also start thinking about strategic partnerships.  I’ve also refined my story a lot during this period and my deck from the “friend of mine” stage looks very different to what I’m pitching today.  I like it better!


This one is obvious but there are a few ideas I’ve used that work well. Here is a good post from Flybridge Partners on the DD process

First customer references.  You will need them and it is a big favor to get someone to go on the record with a VC.  It is also a little scary if you are not there to know how it is going to go. One trick I like is to record the customer interview session and then provide as an MP3 file to the VC.  Its actually quite easy to record (use a teleconference service and record feature) and then have a third party “interview” the customer as if they are a VC asking questions.  Of course you tell the person you are recording and can even tell them you will only send with permission.  Best part is you can ask questions that go to competition, why they picked you, etc and weave a great story.

Another good idea is to create an on-line extranet of all your DD documents.  This way you can simply give access to the room and even get records of what/when items were looked at.  Makes your company look professional too.


You need to bring at least two people to every VC meeting and maybe three.  Not only does it allow you to showcase your depth it allows for a better post mortum review and honest critique of the meeting.  There are however, things to avoid.  Many obvious but I’ve seen these happen … really. In early stage deals team dynamics are almost more important than the technical feasibility.  If VC’s sense any concern what so ever they will go with there gut and pass right away.  Here are some good rules to follow:

  • Agree ahead of time who presents what and how much time to spend on topics.  Know who is QB.  They set the tone, pace, everything.  Follow their lead if they call an audible (i.e. VC walks in and doesn’t want to use the flow you have).
  • Don’t correct/argue (even a little) the person talking on your team.  If a minor mistake let it slip or correct appropriately later but NEVER in challenging factor.
  • Let everyone talk.  If you bring them to the meeting at least have them perform a task or address an area of expertise. Show em/ off.
  • Presenter does not have to be CEO.  Sometimes VP of sales or marketing is simply better.  Have CEO do intro, financials, and leave “details” to others.
  • Body language is important.  Yes — I’ve heard of people falling asleep on pitch team and looking at BB’s … NEVER, NEVER, NEVER!


Some VC’s will caucus after your meeting and only give feedback on call after first meeting.  Don’t be surprised.  It is important to follow-up with an email after the meeting and get any questions/actions documented or out of the way.  If you don’t get feedback live in 48 hours by them reaching out … call and leave a message.  Wait … and call again 48 hours later.  Don’t be a pain but push for resolution.  By the way — if they are really in love they will start chasing you.


This goes really into story creation, DD preparation, and follow-up sections.  It is also obvious.  Look every business has a problem, every person has a failure, every plan has a weakness.  Admit it!  You might avoid an issue in meeting 1, 2, or 3 — but before they write that 7 figure check they will find it out.

My favorite story on this is from my Cabletron days.  The founders on Cabletron (which became a NYSE traded $1.6B annual rev company) could not raise VC money and the founders flunked a personality profile test they were subjected to per tales they told.  Didn’t stop em — they became members of Forbes richest by mid-90’s.


I’ve never seen a VC revisit a “no” answer.  Even if one partner passes others will VERY RARELY look at the deal.  Many dynamics cause this — but if your are turned down don’t hold out hope of a re-connect.  Sure you can go back to friends in a firm and run stories and ideas by them but take them off the list and call’em what they are … PASSED!


The question is often asked … when should I go and get a real job, get the internal round, or close the company.  I’ve been involved with all of these thoughts personally.  I’ve had to close two companies when Series B or C could not be raised for various reasons and also had success when I thought the company was toast.  My favorite example is Sitera where we were really down to weeks in the bank and looking for a new lead.  Long story short — we got the lead and <12 months later sold the company for more and 25x return on capital!

Would welcome your thoughts on the Do’s and Don’t and experiences on raising money from the entreprenrual side!

Get going promoting your company … The Price is Right!

A few weeks ago I read a BLOG post from Dharmesh Shah who writes/created the OnStartups website and 60K member LinkedIn Group of the same name.  He had a particular post recently that I found interesting as it serves as a punch list of things to do if you are a one or two man start-up looking to get a presence on the web and drawing traffic to your idea/people/business (never to early to start in my opinion).  Now much of it is pretty basic on getting a URL, do a blog, etc. but it got me thinking about the changes that have occurred in last few years and the process of getting a web presence and embracing social media.  Not only has the technology improved greatly in the last year alone but with a MUCH LOWER barrier to entry enabling your company/idea cast a much larger shadow.

To give you an idea of how simple it is (and cheap) lets play a game similar to the old “Price is Right” game show where I give a list of items and you guess how much it would cost.

Here goes:

  1. Custom website domain for one year
  2. Hosting service for your website
  3. 100+ email accounts, group calendar, collaboration — with no advertising that you administer and control
  4. Very professional well laid out website customized to your unique needs
  5. Blog site with ability to post via web interface or mobile device
  6. Twitter and LinkedIn, site customized to your needs (note I avoided Facebook for business stuff as I think that is more of use for personal stuff & family)
  7. Ability to add pictures to your blog, twitter or other feeds
  8. Search engine optimization
  9. Google AdWords purchase

Well now guess …

10 years ago likely $100K and leave off items #5 thru #8.

2 years ago you could have all items but it would cost about $20K plus consulting to figure out what these things really meant and a very hard time convincing management to spend.

But if you guessed $17.95 for all of it in 2009 … YOU WIN!

Let me break it down as it is really amazing and how I created a very simple web presence myself for a project I’m working on:

  • Website URL purchase (used GoDaddy and only selected service to buy the domain for 1 year w/coupon for $7.95 — avoid all the other add-on stuff they sell DO NOT NEED!)
  • FREE* Web Hosting (used WordPress and mapped my custom URL to their site so when people go to wadeapp.com it is actually WordPress but hidden from user! Note I did need to purchase $10 credit for URL mapping service* to map to wadeapp.com and used PayPal to buy credit … couldn’t be easier.
  • Group Email (Used Google Apps to have FREE email with custom addresses which I can setup and administer (i.e. wade@wadeapp.com or info@wadeapp.com) Note good instructions here too from WordPress on using GoogleApps and although looks daunting … very easy!
  • Used the WordPress templates they have for free to pick a look I liked and then customized unique home page and sub-pages.  Don’t forget to use widgets for extra info!
  • Signed up for Twitter to setup my Twitter name (wca1) and got the free TweetDeck application to make it easier to follow groups of people and reply (oh and I customized my Twitter background and applied it for a different look).  Note a good way to find people or conversations is to use Twitter Search or Twitter Location Finder Application
  • Made sure my LinkedIn site I use for networking pointed to my website and also advertised my link in my profile
  • Signed up for TwitPic to be able to send mobile pictures to my twitter account via mobile phone (check out http://twitter.com/wca1)
  • By using keywords in Meta tag of word press blog I was able to start the SEO process
  • Lastly used AdWords to purchase a few key search terms (like my name) so that if you Google “Wade Appelman” you find me quickly … it I only bid $.01 per click (guess I was cheap!)

One last thing — I didn’t need to setup a storefront to take in money or sell a product but if you do need a backend — check out this very cool product BravoCart. Other services I use regularly include Constant Contact and Siebel CRM onDemand but more on those usage models another time.

Now this whole effort took me about 4 hours at the most and I did it to learn the latest tools and try out the experience for a project I’m working on that is for another startup.

Try out these steps and tell me what you think and be blown away by the latest options if you haven’t tried it in the last … 3 months or so!!

Patriots Day — Excellent use of video

Yesterday was Patriots Day and less than 1/2 mile from my house over 8000 people descended on Lexington Green to watch the reenactment of the first battle of the revolutionary war.  It was a great day in town with the festivities starting at midnight with Paul Reveres ride and then a day of events starting again at 5:30 AM.

I’ve told my friends over the years about the event (because no one understands that we have a holiday on Patriots Day in Massachusetts) and no one really gets it.  Sure they know guys 20+ years older than the actual participants dress in authentic clothing/uniforms and do a great job of bringing the story to light but they don’t get a sense for the event itself.  Pictures tell part of the story and of course the written word — but a well done video brings you right into the action.

The Boston Globe has a great piece that was posted today here.  I particularly enjoyed, however, the VIDEO and noted that it was created by a friend from town Joanne Rathe.  I know her as the staff photographer for the Globe and always look for her work.  I found this piece interesting because she has done an excellent job morphing from shooting stills to using multimedia to tell the story when required. Now maybe I’ll find out she has done this a lot — but regardless the newspaper world is moving to use “new media” and bringing new technology to bear and I think its great example of telling the story in a new way … using the same staff!  The Lexington Minuteman paper has a good set of links too for additional coverage.

Here is the video:

SlideShare — Cool Tool … but not for faint of heart

It’s been a long time since I posted … but I’ve tried some new tools and I wanted to give a quick review of one.  SlideShare.net is interesting as it lets you post PPT files and add audio track.  I think of it as YouTube for the business set. 

The experience for the end-user is fine as you can simply click the “play” button and sit back and watch/listen. 

Setting up the presentation is not straight forward.  To add an audio track you have to link to an .mp3 stored on some other location on the web and then thru a very clunky interface map your recording to the slides.  It also seemed to die on me a few times — but that was likely a workable bug. 

Bottom line — this is a great way to get out a message cheaply — it is not, however, ready for the average MARCOM employee without a little IT help.

Check out the example from Lightstorm Networks.