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59 Tips for Scaling Startup Sales: Announcing a New eBook from Upshift!

When some of our Upshift advisors suggested we develop an eBook to help encapsulate some of the great teachings that are part of our 12-week curriculum to help accelerate the growth of tech startups, I thought, ok, I’ll add it to our project sprint for that week. Four months later, I couldn’t be prouder of the detailed, yet easy-to-read summary of 59 tips, directly from the mouths of some of our stellar team of advisors, that can help any startup hone in on the process necessary to scale successfully. We all know “learning from mistakes” is part of the drill when it comes to startup growth, but who wants to make mistakes? Wouldn’t it be great if you could minimize some of the pain that comes with turning your passion into a profitable enterprise? In this eBook, startup founders will come to understand some of the common pitfalls made by young companies in the early days so you can do your best to avoid them. For some, it will provide the structure and organization that your company currently lacks; for others, it will be a refresher on what you know to be true about building exceptional sales teams but are too caught up in the day-to-day tasks to act upon it. The eBook is divided into six sections which closely mirror the stages of growth acceleration Upshift implements through its curriculum:

  • Setting Your Foundation
  • Creating Systems & Processes
  • Developing a Sales Playbook
  • Hiring & Managing
  • Testing & Optimizing
  • Scaling for Growth

We’ve interviewed some of the best and brightest minds in startup growth and distilled down their knowledge into these powerful tips, including advice, lessons learned, and “aha moments” from: Arjun Dev Arora, Chairman of the Board and Founder of ReTargeter David Baga, SVP of Revenue & Operations for Rocket Lawyer Andrew Riesenfeld, VP of Field Sales for GuideSpark (formerly, VP WW Sales Development + Pipeline at Responsys) Mark Roberge, Chief Revenue Officer of the HubSpot Sales Division Aaron Ross, #1 best-selling author of Predictable Revenue and The Predictable Revenue Guide to Tripling Your Sales David Skok, Venture Capital Partner at Matrix Partners, and the author of the ForEntrepreneurs blog Navid Zolfaghari, Founder of Pinpoint Mobile (formerly, early team member at Wildfire Interactive) And their advice is not always what you would expect. For example… On Setting Your Foundation,  Aaron Ross says: “Set it up right from the beginning. Dedicate an inside sales team or role 100% to prospecting and generating opportunities to pass on to the Account Executives/closers. This is always priority #1! Plan to segment your inbound and outbound teams; don’t expect the same sales reps to do both.” On Hiring & ManagingArjun Dev Arora says: “Understand that hiring is one part research, one part execution, and one part gut. For the research, investigate what they sold before. For execution, give them an assignment and see how they do. Don’t rely solely on gut; look for signs or past examples of flexibility, consistency, intelligence, follow up and creativity. Do they have a desire to close and win? Are they driven? How badly do they want it? It may be hard to quantify these; that’s where the gut comes in.” On Scaling for GrowthMark Roberge says: “Create your own space and own it.  As competition grows, your original vision may be copied or done better by another company. Don’t duke it out in a bloody battle. Figure out where you excel and focus on that, and market yourself that way. Be prepared to pivot based on market conditions. What works now may not work three months from now.” The eBook includes a special bonus section that shares personal wisdom in the form of What Every Startup Founder Should Know. Here, David Skok candidly advises new Founders: “It’s not a straight line to success; you need to have the ability to go through walls to get to your dream. The journey is much harder than what most people romanticize. Most people who succeed will tell you they’ve had some horrendously hard moments and had to reach deep into their souls to figure out how to survive. You have to have unbelievable fortitude to make it happen.” Of course, you’ll also find lots of advice from me throughout the eBook, as I have definitely learned a few things along the way to founding, bootstrapping and selling my own startups that I would love to share. Together with my partners and advisors, we’re building Upshift to be a premier resource for startups that are ready to take their businesses to the next level. Are you one of them? If so, check out our new eBook and let me know what you think by leaving a comment below. Or reach out to us here and tell us about what your company does and why it’s ready to scale. We’d love to hear from you!

You Can Download Your Ebook Here

What are the Hot Startups to Watch in 2015?

Upshift is dedicated to helping startups grow by scaling their sales teams, and it’s hard to believe how much our own company has grown in just one year! We’ve graduated 15 companies from our sales coaching and acceleration program for 2014, and we’re busy rounding up new promising companies for 2015 to give them the same opportunity to set up the systems and processes they need to scale. So to help us survey the landscape and see what’s hot in the tech startup space, we asked our Upshift advisors to weigh in on what companies they admire, and what industries they think are likely to have their day or make an even greater impact in 2015. Here’s what they told us.

Andrew Riesenfeld

Lots of great minds, from Warren Buffett to Oliver Stone via Gordon Gekko, have talked about “the transfer of wealth,” essentially believing, “wealth isn’t created, it’s transferred.” If you look back on some of the hugely successful new companies, they were all able to create a disruption by using online technologies to help improve an offline process:  not being able to find a taxi (Uber), automating + personalizing the marketing automation process (ResponsysEloqua), even my current company GuideSpark, which enables employers to shift the education + communication process with its employees from offline channels to online channels throughout the employee lifecycle.

The list continues with some of these companies I am fortunate to advise: Take the Interview, which empowers employers to leverage a digital video management platform for interviews to replace time consuming, early stage in-person interviews, and ToutApp, which helps sales teams be better, stronger and faster at closing more deals through it sales acceleration platform. What do all of these companies have in common? They make a process better for both the user and the customer. Even the tablet wasn’t the first of its kind, it’s just that Apple made it better.

So looking forward – any company that has a strong Total Addressable Market (TAM) and can enable a transfer of wealth from offline to online, especially when they have a great leadership team – these are the types of companies I’ll be watching and looking for in 2015. Social selling evangelists like Jill Rowley, Daniel Barber, and Koka Sexton talk about this all the time – how improving the conversion, or the path to purchase, and making it more enjoyable, is what helps to transfer the wealth ultimately to the end user, by making their lives easier and better.

Andrew is currently VP of Field Sales at GuideSpark and the former VP of WW Sales Development + Pipeline at Responsys, where he helped lead the company to an acquisition by Oracle for $1.6 billion.

David Baga

I think we’re at the forefront of three major trends that will impact the next year and beyond:

1) Data science. We’re at the very early stages of realizing what’s possible with artificial intelligence and we’re going to see significant progress in 2015. Natural language processing, machine learning, and data mining are all maturing, and the applications in both B2C and B2B are endless. The next wave of software companies will build data science into their solution from the ground up rather than bolted-on afterthoughts. Companies like Entelo in recruiting and RelateIQ in sales enablement, and 6Sense in marketing automation, are a few examples of companies that built their solutions around data science.

2) Mission-driven startups. For the last couple of years, the blogosphere and the media have increasingly challenged the Silicon Valley community to build technology solutions that will contribute to society. We’ve already begun to see the reaction: startups like Clever are tackling educations, Grand Rounds and Stride Health are improving access to and quality of healthcare. It’s just the beginning; I think we’ll see more meaningful startup ideas come out of Silicon Valley for years to come.

3) Verticalization. Over the last decade, we’ve seen a lot of SaaS companies do a great job of replacing broken offline workflows and on-premise software. Now, there is a great opportunity for companies to verticalize and create complete experiences for entire industries. Emergence Capital has done some great work in the area of industry clouds and had a great outcome with Veeva Systems in 2014. I think we’ll see more of the industry cloud model in 2015.

David is SVP of Revenue & Operations for Rocket Lawyer where his team has grown revenues from $2 million to over $40 million in just four years. David spent seven years at Oracle, building and leading sales teams that delivered record-setting results.

Navid Zolfaghari

I think the big winners will be those companies that are able to understand how their online marketing influences offline activity. 90% of commerce happens in brick and mortar settings and this represents trillions of dollars. Understanding the full consumer journey has always been a blind spot, but now the technology has risen to be able to figure out what types of ads actually result in people walking into a store, making closing the loop between online and offline a real opportunity. And then you have companies like Google that are doing such innovative things like the Self-Driving Car, Project Loon (balloon-powered internet for remote and rural areas), smart lens technology (to treat ocular diseases using contact lenses) – this is where some of the brightest and best minds are working to change the world.

Navid is the Founder of Pinpoint Mobile, formerly the Founder of TriFame online talent discovery site, and an early member at Wildfire Interactive, which was acquired by Google in August 2012 for over $400M.

David Skok

There are many areas in which there is tremendous innovation right now. This is one of the most exciting eras we’ve ever lived through because of the evolution of three new platforms, the combination of which create an unbelievably potent computing platform. These are:  mobile, social and cloud platforms, all working together. The power of a portable mobile device – carried around, minuscule, always with you, always on – combined with the full computing power of the cloud, means any operation can be bigger that what can be done on the phone alone.

An example of this is Waze, which not only has the ability to transmit GPS driving instructions, but, by connecting with the cloud, and also using the shared capabilities of multiple drivers, you now have a faster routing engine than with the phone alone, or with social alone. The shared power of all of the social drivers sharing the speed at which traffic is running on certain roads is an example of how these three technologies can be used together. Companies that creatively leverage these three new capabilities to solve problems in new ways are going to be the big winners.

David is a serial entrepreneur turned VC.  He started his first company at the age of 21, and over the next 25 years, founded a total of four companies and oversaw one turnaround. He is currently a venture capital partner at Matrix Partners, the firm that had backed his last two companies.

Mark Roberge

From a very high level, when it comes to software and technology, I think in the last five years the hot space has been people management/HR, with companies like Workday and Concur. More recently, marketing software like our company, HubSpot, along with Marketo, Eloqua, Pardot and ExactTarget, have been a huge focus. In the next five years, there’s a new category that not a lot of people see but is on the rise, and that’s the space of sales enablement and sales acceleration, which really fits somewhere between marketing software and CRM.  For the first time, we’re seeing technology being focused on the sales person and making their job faster, and enabling them to create a better buying experience for their customers.

Mark is the Chief Revenue Officer of the HubSpot Sales Division. HubSpot ranked #33 on the Inc. 500 list of Fastest Growing Companies for 2011, and Mark was ranked #19 in Forbes’ Top 30 Social Sellers in the World.

Arjun Dev Arora

There’s a lot that’s going to be happening in the Internet of Things (IoT) and data connectivity in and around IoT. In addition, the “now economy” will continue to grow – examples include Uber, Lyft, Sprig and Spoonrocket. These speedy food delivery companies in particular will continue to grow, but we’ll also see them become verticalized for things like pizza and healthy food options. The restaurant industry as a whole (in particular fast casual) will start to change as a result of these companies. Not that people will stop going to restaurants, but food delivery models are changing, starting with GrubHub and Seamless in the first wave, then these others in the second wave. This space will continue to become more efficient and interesting over time.

On the enterprise side, there will be more data that lives within organizations, particularly within email services that will now be able to be leveraged.  Email is critical to day-to-day business, we’ll see more of a verticalization of email clients – for example, real estate agents will have a different email experience or email client than a sales person – we’re already seeing that with RelateIQ and Salesforce. As more data gets pumped in, we’ll be able to know how long someone spent on the email, if it was opened, if it was forwarded – we’ll have better built dashboards to better understand communications within enterprises.

Arjun is the Chairman of the Board and Founder of ReTargeter, where he bootstrapped the company to be in the top 100 of the Inc. 500 list of Fastest Growing Companies for 2013.

Wow, lots to think about (and look forward to!) but it looks like verticalization is coming, along with continued advances in sales and marketing automation software and basically, just continuing to make people’s lives easier in ways we haven’t even begun to imagine yet.

What companies or industries do you think will be hot in 2015 and beyond? Tell us about them below.


Upshift’s Year in Review: Congrats to our First 15 Graduates!

Here we are at the start of a new year and I can’t believe how much we at Upshift, as well as the tech startup industry in Silicon Valley, has to look forward to. It’s never been a more exciting time to be part of the innovations that are changing—and improving— the way people do things every day.

At Upshift, we’re even more jazzed about the potential of today’s startups because we’re helping to grow their businesses faster than they could on their own, and in a way that’s sustainable to keep them thriving.

Upshift, still less than a year old, already has graduated 15 companies from our sales acceleration program, the first five of which raised over $215 million in follow up funding within six months  of completion. If you know me, you know I’m not shy about saying WE KICKED ASS by kicking the asses of our program participants so that they could be successful.

How did we do it?

Part of the beauty of Upshift is, we’re not just teaching the companies in our program how to scale, we’re committed to sharing information for the community at-large to help them kick ass as well. Part of the plans we have for 2015 is to post in-depth case studies on how we moved some of the companies in our program from Point A to Point B. Quite candidly, it’s too much to talk about here since each company is different and each deserves their achievements to be highlighted in a way that can be fully absorbed.

What did we learn this year?

When we first started out in March of 2014, we had a concept – to help accelerate the growth of Silicon Valley startups. I had experience scaling companies through my own businesses, and learning from my own mistakes as well as the mistakes of others, is a key tenet of our curriculum. We learned as much from the companies that came through our program as they learned from us. They learned how to develop a structure for their sales process, and we learned how to take our experience and turn it into an actionable blueprint for them and other companies to follow. In the 10 months since launch, we made several iterations to the program and continually grew and standardized it based on what we identified as the areas in which the companies needed the most help.

Did we meet our expectations for our first year?

I’d say things have gone better than we could have hoped for. Back in March, there were two of us working on two companies at a time, and taking between four to five months to execute our scaling process.  In the fourth quarter of 2014, adding Julian Pisani to our staff helped us to expand to six companies working over the course of three months. Not only have we learned to streamline our process so that it’s faster, we’ve also learned how to add more value and take on additional capacity – now that’s scaling!

What did we learn from the companies participating in our program?

Looking back, I’d say it comes down to five things that startups need to focus on:

1 – Don’t boil the ocean.  Startups don’t struggle because of lack of potential customers, they struggle because they’re going after too many prospects at once. It’s important to hone in on the customers most likely to be interested in your product or service. Don’t go after everyone.

2 – Data is essential. Many companies in the early stages set out flying blind and relying on emotion over data.  They make gut decisions about strategic directions that can very often prove wrong or misguided. It’s important to accumulate data early on, and analyze it so you can begin to identify trends as to what’s really working. You need transparency in everything you do and you need to back your decisions with data.

4 – Learn how to prioritize. Another setback that tends to befall startups is a lack of execution or prioritization. Often startups are doing a lot of things, but because they’re not prioritizing what’s most important, it inhibits their ability to execute on the things that matter most.

5 – Every house starts with a blueprint. Often companies have a process or structure for the way they go about customer acquisition, but if it’s not documented and only the founder knows what it is, then you can’t scale. It’s like trying to build a house without a blueprint.

What’s in store for Upshift next year?

We are continually focused on identifying the areas we can leverage most to help scale startups rather than doing everything. (We take our own advice!) So we’re taking another look at the program to reevaluate what we can do to be even more productive in 2015. And in keeping with our commitment to the greater startup ecosystem, we’ll be rolling out a great deal of content here on the blog and throughout our site, and making it free to startups to help them expedite their own learning curves.

The first of these initiatives will be an eBook with advice and tips from several of our Upshift advisors – the kind of advice most startups would kill to get in their early stage – we’ve culled it and couldn’t be more excited to be putting it out there. Of course, we’ll also be making core revisions to our program to help the companies we bring on board and give them the best experience we possibly can. As a sneak peek, one of the areas we’ll be looking to focus on will be helping startups implement a management structure for high performing teams and ensure that all the companies going through our program can execute on that.

To get an idea of the types of companies that can best benefit from Upshift’s program, take a look at our first 15 graduates. We couldn’t be more proud of their accomplishments and can’t wait to see where they go from here.

Betterdoctor – Discover the best doctors in your area
Boomtown – The new age of tech support
Boomtrain – The only personalized marketing platform with artificial intelligence at its core
15five – Stay connected with your employees, projects and culture as your company grows
Honeybook – Delightful, simple tools for event professionals
Massdrop – Bringing enthusiasts together
Metromile – The smart approach to car ownership
Pathbrite – Capture and share your projects
Proven – Easy, Elegant Hiring.
Supplyhog – Built from the ground up to better connect vendors and manufacturers with customers in the construction industry
Symphony Commerce – Commerce as a service
Thanx – Use your credit or debit card to earn free stuff from your favorite merchants
Ubiquity Retirement + Savings – The smart way for you and your small business to start saving for retirement
Whalepath – The largest marketplace for market research and competitive analysis
XTV – Connected TV and media management platform

In terms of scaling our own company, we’re planning to double our staff, if not triple it, in 2015, to accommodate 50 companies. Will yours be one of them? If you think you’re ready to scale, leave a comment below or email me at We’d love to hear from you!






A Look Back: Sales Hacking Bootstrappers Guide – Deep Dive #2- Stop Pitching

Earlier this year, we ran a two-part series of deep dives on the bootstrapping process based on my own personal experience. In these posts, I broke down my sales process into easily digestible steps that anyone can follow when it comes to selling just about anything. The posts were so well received that we thought we’d highlight them again for you now when, hopefully, you’re spending a lot of time thinking about how you will grow your business in 2015. Be sure to stay tuned to the Upshift Dispatch throughout the year, we’ve got lots of great stuff on tap you won’t want to miss!

Here is Part 2, and if you missed a look back at Part 1, make sure you check it out here.

If you’ve been following my posts here on the Upshift blog, you know that: 1) I posted a detailed guide giving away my trade “secrets” for succeeding as a bootstrapped business, and 2) it was so well received that I decided to go into more detail on the points presented in response to your comments. You can read my first deep dive on the 80/20 rule which addresses many of your questions about how to identify your best customers and create more of them. Here, I’ll be focusing on your questions about how to get new customers without ever doing a sales pitch again. (Okay, I’ll admit, that’s a “buzz” term my marketing folks want me to use to get your attention. I don’t necessarily think there’s anything wrong with a “sales pitch,” it’s just that so many of them suck that it’s given the whole concept a bad rap. So for the purposes of this post, forget about pitching.)

How did you grown your business from $2,000 to $2,000,000 in sales in just four months without pitching your product? I provide great detail into how I accomplished this in my first post in this series, the Bootstrappers Guide. Here, I’ll tell you that I had a lot of doors slammed in my face along the way. Like I said, the idea of a “sales pitch” has a bad connotation. What I’m proposing, simply put, is, rather than go in with your sales pitch, offer something of value before asking something from the other person. Interesting idea, huh? Just a slight reorientation of your intention can shifts the dynamic a little bit, hopefully a lot. We hear sales pitches everywhere we go, and we get immune to them. We cringe at the sound of anything resembling a “pitch.” Don’t get me wrong, the entrepreneurs out here in Silicon Valley are selling the vision for their companies to the VC’s on Sandhill Road every day and raising millions of dollars in the process. Are they doing it with a sales pitch? Maybe. But I’ve seen that the ones that are getting money are the ones that are educating and solving problems, not selling.

The Takeaway: Don’t pitch your company/product/idea; rather educate your prospect. Discover their pain point and tell them how your company/product/idea can help.

It can be so demoralizing when you gear up for a big pitch and don’t get the business. Any tips on how to handle this and keep knocking on the doors? Doors will get slammed in your face. I know, I literally had my nose pressed to thousands of them when I went door-to-door over a series of summers while building my first business. You need to develop a thick skin. Those entrepreneurs that develop that skin and keep going are the ones that have built really successful businesses. If you can walk around and get used to doors being slammed in your face, congratulations, you’re an entrepreneur! In more practical terms, if you spend one-half hour with a customer and don’t close the sale, ask yourself:

  • Have you educated someone about your industry or product?
  • Have you helped them in some way?
  • Have you left an impression?
  • Have you built trust and respect?
  • Have you made a connection that could potentially call you in six months, should their circumstances change?

The takeaway: If you can walk away from a meeting believing that you’ve accomplished at least one of these points, it wasn’t an unsuccessful sales meeting. Develop thick skin.

I find it hard to work on pitching my business or raising funds when I’m still ironing out our product and dealing with the day-to-day issues that come up. Can I delegate this to someone else? It depends on what stage your company is in. For early stage companies, you as the founder absolutely should be involved in the marketing and sales of your company. You need to hear firsthand the feedback that’s coming in on what you’re putting out there so you can work to make improvements. There are other things that you can find others to do, like operational tasks. Find someone you trust to handle opps and focus your energy on how to get customers.

The takeaway: No matter how great your product or idea is, you won’t go anywhere with it if you don’t get yourself some customers.

In your Bootstrapping Guide, you talk about continually following up with prospects with calls and gifts every week. How adamant are you about these “stalker” tactics? Pretty adamant. That’s because I’ve seen the payoff. There’s a fine line between being persistent and being an asshole that no one wants to talk to. Obviously, I’m recommending the former. By repeatedly sending key prospects something funny or clever, eventually they realize you’re serious. So even though nothing might typically happen the first few times, it’s that one golden moment when the CEO of a prospect company calls and says, “Okay, you’ve got my attention, what can you do to help me? — that makes it all worth it.

The takeaway: Calling and pestering doesn’t accomplish anything. But if you really think about how to stand out when you’re making those calls, then you’ll get noticed.

Okay, so if I’m going to be a stalker, do you recommend a specific time of day or week or days to reach a contact by phone, email, social media? Companies have to discover this for themselves, but what’s key here is that most entrepreneurs don’t take the time to try different tactics and track what’s working. An early stage company, in particular, should be reaching out to prospects at different times of the day, and different days of the week, and measuring the success rates of each tactic. The results might be one thing for a healthcare company versus a SAS company or a BtoC company, so try different things and see what works the best. A later-stage company should have a more sophisticated CRM tool in place that records the highest response rates for email, phone calls, etc.

The takeaway: Take a step back, look at your results, see which 20% is working best (see more about this in my post on the 80/20 rule), and then refine your strategy.

Can you share some examples of offers that have worked for you in the past? Again, what worked for me may not be exactly what works for you. But I’ll tell you what we did for my marketing consulting company that brought in new business. We sent prospects:

  • A $2 bill

With the tag line: This $2 bill is magical; it multiplies when you spend it on generating more traffic to your website. And the solution: Let us prove it to you.

  • A sticky hand

With the tag line:  Are you concerned that your marketing programs aren’t sticky enough? And the solution: Call us we’ve got some great glue!

  • A flying pig figurine

With the tag line: The only time your conversion rate will increase is when pigs fly. And the solution: Unless you call us!

  • A pen with a flashlight –

With the tag line: Do you feel in the dark about how your marketing results are going? And the solution: Give us a call; we’ll help shine a light. There were a lot more but you get the idea. We sent one of these little gifts in succession every week; some funny, some compelling, but always with a message that showed we were serious.

The takeaway: In all of these cases, the key was to think about the pain point they have and how our service addressed it, but in a fun and clever way. (Okay, maybe cheesy in some cases you might think, but it worked.) Think about what will work for your business.

So, why are you giving away all of your trade secrets?
I’ve done this already; I’ve built my businesses and I wish that someone had given me this kind of advice when I was coming up. I’m not saying my process is the be all and end all; just that it worked for me. There are lots of ideas out there but what makes the best ones rise to the top is testing and execution. I like to drill it all down into a step-by-step process, learn what works and what doesn’t, and try to adopt the things that work. A lot of this basic information was missing when I was started out; I sincerely want to help others avoid the same mistakes I made.

It’s important that new ideas get out there. That’s what my current company, Upshift Partners, is all about. We at Upshift want to see companies succeed; we want to see entrepreneurship thrive. Our core mission is to help increase the success rate of startups. And to do this, we are continually learning, uncovering new concepts and ideas that help the companies we incubate. We’re out there trying to improve our program and learn from the companies we work with so we can help them and others succeed. So I guess that’s why I’m really doing this.

What else would you like to know about the sales pitch or any other part of the startup process? Leave a comment below and I’ll either get back to you here, or address it in an upcoming post.

A Look Back: Sales Hacking Bootstrappers Guide: Deep Dive #1 – The “80/20” Rule

Earlier this year, we ran a two-part series of deep dives on the bootstrapping process based on my own personal experience. In these posts, I broke down my sales process into easily digestible steps that anyone can follow when it comes to selling just about anything. The posts were so well received that we thought we’d highlight them again for you now when, hopefully, you’re spending a lot of time thinking about how you will grow your business in 2015. Be sure to stay tuned to the Upshift Dispatch throughout the year, we’ve got lots of great stuff on tap you won’t want to miss! Here is Part I.

Back in April, I posted here about my experiences hustling, eh building, my online directory software company from $2,000 to $2,000,000 in sales in just four months. I knew it would be a challenge—distilling all of my hard-earned wisdom into just a few hundred (okay, thousand!) words—not building the company—although that was a challenge too, but of an entirely different sort. So I broke down my process into easily digestible steps that anyone can follow when it comes to selling just about anything. And you responded. So I thought it would be helpful to hone in on some of the steps I covered in my last post, based on your questions, comments, and just stalking me in the street to find out more. This post will cover the 80/20 rule; my next post will cover sales pitches (and why you should never do them). To summarize:

  1. Selling is bad. Educating is good.
  2. Figure out who your best customers are and then find more of them.
  3. Be prepared to do a lot of research, or hire someone to do it for you.
  4. Be persistent, not just in your vision but in your tactics. There’s a difference.
  5. Knock on doors—literally and figuratively—to make the sale.
  6. Get used to doors being slammed in your face—congratulations, now you’re an entrepreneur!

So to dig a little deeper into your questions and concerns, I’ve selected some representative comments here. It helps a lot if you read my first post, but I’ll try not to make too many references that seem out of left field. Oh go ahead, read my first post. I’ll wait…

 1.   I like your breakdown of the 80/20 rule, but it seems my 20 in each category is a tough nut to crack. Is it really that important to identify the 20% of your business that’s working? Is it really that scientific?
Yes, it’s scientific. Yes, it’s important. But it doesn’t necessarily have to be an 80/20 ratio. In every company that I’ve run or worked with, there’s always been a minority percentage that accounts for biggest impact on revenue and I believe the 80/20 rule applies across all types of companies, generally speaking. It could be 90/10, it could be 70/30 but the idea is essentially the same. In a sales organization, for example, it’s likely that 20% of the team produces 80% of the sales. The same holds true for marketing, where 20% of your marketing brings in 80% of your new customers. The learning here is: don’t always focus on everything, but on the most important things. It may not be 80/20 every time, but the practice of going through and evaluating what you’re doing can help you to realize where you should be spending your energy. Find that 20% that’s working.

2. Okay, once you identify your 20%, how can you replicate them?
It all comes down to attributes. Taking a broad view, if 20 % of your sales target is performing the best, there is likely a group of characteristics—like how old they are, where they’re from, what school they went to—all this can prove predictive of the next group with these attributes being successful. It works the same for customers. Find the percentage, whether it’s 10, 20 or 30, that account for your lion’s share of revenue, then look at the attributes of those people. It may sound simple, but many businesses typically don’t do it. I’ll say it again: find the ones that account for the most revenue; then figure out the attributes they have in common.

3. What if you’re just starting out and you don’t have enough for a representative sample of 20% success?
Take your best guess. Ask yourself

  • Who are the people most likely to need my product?
  • What is the biggest problem they have?
  • Where are they spending the most money to fill a need?

Try testing different things to find out what or who are your best performers. For example, if you sell HR software, ask yourself what companies have the biggest problems that your software addresses? Who are the companies with the highest turnover or who are hiring the most people?  Then ask yourself, how old are these companies? It may be that the more up and coming businesses need what you offer. Take your best guess and try to narrow your focus. You may start out going after everyone, but eventually you’ll need to look at your numbers to make concrete decisions as to what’s working the best.

4. No, I mean we’re really starting out. We’d be happy to have 20 customers, let alone the figure out who the best 20 are.
If you are hell bent on an idea for a company, then you have something you feel people want.  And you must have some idea of who it’s for; you had to cover that in your business plan. My advice to you is, be careful as you expand. Taking on everyone who says “yes” to your product might not be the smartest strategy in the long term. After the seed phase, you need to go back and refocus before putting any more money into growing your company. You may have signed up only15 customers but if 10 of them aren’t good leads, you’re better off finding more of the 5 who are. Identify what makes the 5 good, and set out to find more of them. Even if it means you have to fire a customer. This is especially true for early stage companies, when you are moving really quickly. If a customer just turns out to be a big drain and isn’t giving you good feedback, move on. Just like in life relationships!

5. Do you have to have your 80/20 strategy in place along with production and operations from the outset?
In the beginning, of course, you have to build the product you think people want but you also have to find the people who want it, who are willing to give you their money and who you’d like to keep as customers. These are the two components I see a lot of new entrepreneurs not putting enough focus on and it could be the deciding factor of what could makes or breaks your company. I hope this answers your questions about the 80/20 rule discussed in my last post, but if you still have anything that’s eating at you, leave a comment below. And please, shoot me some ideas for what else you’d like to see me address in coming posts, I’m here for you!

Is Your Startup Making One of These Deadly Sales Mistakes?

Here’s an excellent recap of my presentation last week at the Sales Hacker Conference from an attendee, Tony Perez, CEO of Sucuri and blogger at Perezbox.

In his post, “10 Deadly Sales Mistakes Startups Make,” Tony says he was “pleasantly surprised with the content and caliber of information being shared” at the event and that he was “especially keen on one talk,” by, well, me!

So don’t take my word for it; see what this founder/blogger has learned for his own business when it comes to the top mistakes startups make and how to avoid them.

Thanks, Tony, for the shout out!



3 Lessons Learned from Bootstrapping Sales from $0 to $20 Million


Eight years ago, I started a tech company in Silicon Valley without an email address or computer and bootstrapped it to over $20 million. And I did it without a penny of outside funding.

If I can do it…anyone can…

To say that my journey is unique is a huge understatement. I didn’t go to an Ivy League school; in fact, I dropped out of college. I didn’t get funded by a VC; instead, I bootstrapped my way along on credit cards and home equity lines of credit. Growing up on a hippy commune, I didn’t have many examples of what it meant to be an entrepreneur. We had no electricity, internet, or televisions and the only entrepreneurs I knew were in let’s just say, “farmers.”

How did I do it?

Here, I’d like to share three powerful lessons I learned the hard way in the hopes that you don’t have to make all the same mistakes that I did.


Lesson 1: Do More With Less



In this lesson you will learn:

  • How to focus on the customers that have the most pervasive and urgent need
  • The importance of a top 10 and bottom 10 analysis
  • Mo’ money = mo’ problems

My Story:

My partners and I were running a marketplace for local services called Calfinder that –with a bit of tenacity, the ability to tap an untapped market and perhaps even luck – we were able to grow to about three million in sales. (More on how we did this in Lesson 2). But eventually, we found ourselves stuck. You see, like many entrepreneurs, we were incredibly ambitious and wanted to continue growing as fast as we could – our goal was doubling revenue each year. I wondered what we would have to do to accomplish this and was feeling deflated.

At that time we were still struggling to hire the right salespeople – we were generally hiring about three people to find every one top performer. Running the numbers I saw that in order to accomplish our goals we were going to have to triple our sales team. But I had to find a way to accelerate the process. I started digging through our customer list and saw two of the companies in our top ten were spending almost ten times what the average customer was spending. I knew I was on to something…

Then I hired a freelancer through Elance to research both our top- and bottom-performing companies to gather other attributes on them like:

  • how many counties they covered
  • how long their website had been up
  • what our entry point had been into the account

When I got the spreadsheet back I sat down (with some beers) to analyze it and found that there were a few key attributes shared by these exceptionally profitable customers. I then built a list of 100 more companies that matched this same criteria. After building the list, I designed a coordinated campaign to hit them from all sides – phone calls, emails and attention-getting gifts sent in the mail. Then I executed on my plan – sending out the mail pieces each week and ensuring that each of our 100 prospects got a follow up phone call. To my surprise—absolutely nothing happened during the first four weeks of my brilliant campaign.

As I sunk back in my chair (with another beer) to doubt myself even more, it happened. My phone rang and it was the CEO of a multi-billion dollar company. He said…”ok, you’ve got my attention, how can you help me?” The next week I got another call and then another one the week after that.

Four months later, we had signed up over $2 million in contracts and after tallying up our total spend, it cost us around $2,000 and we didn’t have to hire a single new salesperson.

What I Learned:

It’s not only the power of hustle to get results, but the incredible power of doing less, but with focus. If we were flush with VC cash the odds are that we wouldn’t have been as creative or willing to put our foot on the gas. Or, we would have been doing so many things at once, we would have given up a lot sooner before seeing any results. Focus.

The Takeaways for YOU:

  • If you’re just starting out, pick a market with the most urgent, pervasive and costly problem that you can solve.
  • If you’re already running, take a step back in order to take a huge step forward.  Analyzing the attributes of your top and bottom ten customers; then look for 100 more that match the criteria of your top ten and pursue them with all that you’ve got. Read more on this in my post: “The 80/20 Rule.
  • Once you’ve identified your prospects, be relentless about contacting them; but be creative and smart, too. Read more on this in my post: “Stop Pitching.”


Lesson 2: Make the System the Hero



In this lesson you will learn:

    • A better playbook = faster growth
    • Document everything that you do more than twice
    • The importance of iterating weekly

My Story:

When we came up with the concept for Calfinder – a marketplace to connect homeowners with local service professionals – we didn’t know how to build a website, use software or even spreadsheets. In order to test the business model, four of us wrote down a script on yellow note pads and went around to houses asking people if they would want to get free quotes on household projects. To our surprise, when we all met up at Starbucks at the end of the day we had collected 10 leads!

The next day we wrote another script, this time geared to service professionals, then looked in the Yellow Pages to find contractors with the biggest ads to see if they’d be willing to pay to get connected to the homeowners we identified. We set up three appointments for the following day. We asked the contractors how much they’d be willing to pay for leads – the names and phone numbers of the people we knew wanted work done. The first one said “$80,” we literally made a photocopy of the yellow piece of paper and sold it to them on the spot. A company was born.

We took the money, refined our script and hired college kids from the local campus to knock on doors for us over the next weekend – that brought in 30 more leads.

We repeated this process, continually refining the script and process for months, all while documenting everything in the system, testing it and iterating on it every single week.

Over the years this helped us to go from 0 to 50 salespeople and run a highly organized company with a relatively small staff.

What I Learned:

I’ve never forgotten that hustle and documentation go hand in hand and build upon each other to create momentum. I’ve taken this process with me to every company I’ve started and every company that I advise and invest in.

The Takeaways for YOU:

  • Your playbook is one of the most important things you will create as a startup
  • Document everything you do more than twice
  • Review weekly to start, then start reviewing monthly


Lesson 3: Let Data Drive Decisions



In this lesson you will learn:

  • Why you should let data drive decisions
  • How to manage by the numbers
  • How to remove ego from decision making

My Story:

We were up to a 50 person sales team at Calfinder and closing four times the number of deals than we were before…but…when I looked at the data for previous 6 months I saw that we had actually lost $1 million ramping up the team and though the deal volume had increased sharply, we hadn’t seen any boost in profits. In fact, churn had increased significantly which meant that the lifetime value of our customers was cut in half.

We were on a very rough road; one that called for a serious correction.

Again, we dug into the numbers looking at churn by rep, average deal size and customer happiness, as measured by repeat business.

We found six salespeople that were profitable and in order to save the business from going under we made one of the most difficult decisions of my career – letting go 42 salespeople (84% of our sales force!) and going back to the drawing board.

Sometimes difficult decisions pay off. After our layoffs we focused on the specific, measurable things that made these six salespeople so successful. We looked at every attribute and approached it like a science. And we found some very interesting similarities in terms of:

  • where they came from
  • the approach they took
  • the specific customer segments they were going after

We then emulated everything they were doing and cut out a lot of what we “thought” made for a successful salesperson, instead only focusing on what the data told us.

Over the next 12 months we grew revenue by over 50% with a team of 6 and eventually, Calfinder grew to become a $20 million business. Did I mention we started with nothing?

What I Learned:

Less is more when you’ve figured out what works the best. Just do that and forget about the rest of it.

The Takeaways for YOU:

  • Don’t let the highest paid person in the room make decisions that aren’t supported by data
  • Don’t let your ego get in the way of doing what needs to be done
  • Don’t try to scale until you really have a good understanding of the metrics that lead to success

Do you have any of your own stories of how bootstrapping sales worked for you? Tell us about it here, or ask me a question about any of it below.

How to Increase Productivity

When I first started my company we didn’t have meetings and we learned how to increase productivity. If you needed something or had a problem you could just speak up or get a partner’s attention by throwing something across our 400-square-foot garage turned “World Headquarters.”

Don’t stop hustlin’ on those b2b sales

48% of b2b sales people never follow up with a prospect;
25% of sales people make a second c ontact and stop;
12% of sales people only make three contacts and stop;
Only 10% of sales people make more than three contacts.
80% of sales are made on the fifth to twelfth contact.