Secrets of a successful enterprise software startup founder

Enterprise sales complexity

It seems every entrepreneur wants to start an enterprise software company. However, many of these founders do not possess a realistic understanding of what selling to the enterprise actually means.

While it is true that enterprise budgets can be large, convincing managers to buy your products is often difficult, complex, and time-consuming. Enterprise buyers tend to be risk averse and have a carefully defined process for evaluating products and vendors. Thus, enterprise selling can be a slow and expensive trap for startups that are unprepared.

On the other hand, for startups that get it right, enterprise buyers offer a great way to gain product feedback, references, and revenue.

Although CXOTALK usually highlights stories about digital transformation and innovation in large organizations, now and then a startup catches our eye. I became interested in Helpshift because they have cracked the code on enterprise selling.

Helpshift has raised $36.2 million and counts companies such as Zynga, Target, and Virgin Media among its customers. Microsoft is also a customer and Helpshift provides the chat support infrastructure for mobile apps such as Outlook and Office.

When founder, Abinash Tripathy, started the company, he envisioned a future in which software companies and app developers would need to provide direct methods to offer in-app support on mobile devices. Solving this problem required Helpshift to build an infrastructure that can handle millions of help transactions every day.

I asked Abinash to be a guest on CXOTALK and explain how Helpshift entered the enterprise and managed to build relationships that companies such as Microsoft consider mission-critical.

We spoke for 45-minutes, creating a treasure trove of information valuable to both enterprise buyers and founders. Among the key points:

  • Startups that want to compete in the enterprise must endure long sales cycles and an extended investment horizon
  • There are benefits of being an enterprise company from the start, but it requires patience and founders who have expertise in the large enterprise segment

You can see a summary of our discussion in the short video embedded above and read a transcript here. Of course, watch the entire show and read the full transcript at the CXOTALK site.

Michael Krigsman: What about the sales cycle? As a startup, how did you manage that aspect of it?

Abinash Tripathy: If you’re selling to the enterprise, and you’re consciously building an enterprise to sell to the enterprise, all of those things are a given. You have to do those things to be able to sell to an enterprise, including the long sales cycles.

If you don’t have that experience in the Valley and you’re trying to build an enterprise company, you won’t see the value of working with these companies, being patient, and investing up-front to go work with companies of that size, and you’ll always go after what’s easy. So you see a lot of these B2B companies in the Valley, they do what’s easy. They’ll go after small companies – five, ten person companies – that don’t have a lot of complex requirements and build for them. Then they find that it’s really hard to move upstream, and sell to the enterprise.

And, you know, there’s a reason why Salesforce is Salesforce, and Zendesk is Zendesk. They’re two different-sized companies, from a revenue and size standpoint, and they probably have an equal number of customers, right? The revenue difference is 5 – 10x, right? Because one sells to very large enterprises, and the other one sells to sort of, you know the long tail.

Michael Krigsman: What is the advice that you have towards startups who want to sell to the enterprise, but they look at these long sales cycles; in many cases, getting introductions is hard. But once they have an introduction and the sales cycle, the need to invest is very, very difficult. It’s just that delay, that time, is so expensive for a startup and it’s cash that they don’t necessarily have and time that they don’t necessarily have.

Abinash Tripathy: Yeah, so for companies that sell to the enterprise, the scaling and the growth is slower than those selling to the SMB, initially. So, let’s say you take two companies: one selling to the SMBs and the other selling to the enterprise-sized companies, and they start their journey at the same time. Chances are the SMB-focused company will scale much faster than the enterprise-focused company in the initial years, right?

And, so after the three-four year mark, it looks like the SMB company is ahead. But then, once that market starts to peak out, or, you know, bottom out, and it happens very rapidly in those sort of SMB segments where you run out of all the SMB that company can sell to, and then you make the decision to go up-market, and then your product is nowhere near close to being up-market at that point. Any company… I haven’t seen a single SMB-focused company become a successful enterprise company. I haven’t seen any examples of that. Nor have I seen examples in the reverse where you see enterprise-focused companies being really good at selling to SMB. I think they’re two separate markets, they’re two separate needs or requirements, and different types of companies will cater to those segments.

That’s really…So, the biggest thing, coming back to your question, which is “What do you really need to do to be an enterprise-class company?” The first thing you need to do is you need to know that you are building a long company or a long-term company. You need to find patient investors, investors who have the patience to build a longer-term, enterprise-class company and are not looking for that SMB, fast-growth kind of model. So, it starts with picking the right investor. In the Valley, there are those investors that really want the rocket ship, B2C-style, no-sales kind of companies. They basically tell a founder, “Oh, you should not have any salespeople at all; it should only be inbound marketing,” so there are investors that prefer that. And then there are investors that believe that “You should start working with large enterprises. It’s going to be slower. Build an outbound team.”

And the two types of companies are very different. If you’re looking at the SMB companies, they’re investing a lot of dollars in marketing, in digital marketing, and not as much in sales. And you look at enterprise-focused companies: fewer dollars in marketing, more dollars in BDR [business development resources], outbound, inbound, having account reps and inside sales. Very different models, right?

Now, the other thing I’d like to add is if you think about how we grew as a company before we built our sales, the BDR, SDR machinery, the first thing we invested in was customer support and customer success. Because, when you work with enterprise customers, they are big brands, and you don’t want to fail them, so you want to make sure you have the best customer support and customer success teams in place to handle these big accounts and make them successful, and they become case studies. They go around to the world telling them how good you are as a solution provider, and then companies in their class come in, inbound. And when that engine starts to work, it’s very powerful.

Abinash Tripathy: My biggest advice is if you don’t have a co-founder that has worked in the enterprise category or space, selling or in BD [business development], then get one. You need a person that understands what it takes to work with enterprise companies. That’s the first and foremost requirement.

And, the second one is to find patient money. If you want to build a long-term enterprise company, you going to want a VC that is patient and knows what you’re going to be doing, and it’s going to take some time and is willing to work with you and help build the company. And so, patient money is really important.

I think those two things, if you’ve got people who have the experience that you need for enterprise, and you have patient capital, then I think you’re on your way. It’s not that those problems can’t be overcome, it’s that those are the two things, the foundational elements.

To see the list of upcoming CXOTALK episodes, click here. Thank you to my colleague, Lisbeth Shaw, for assistance with this post.

(Cross-posted @ ZDNet | Beyond IT Failure Blog)

How I Promise You One of the Most Meaningful Days of Your Life

I know the title “I promise you one of the most meaningful days of your life” sounds grandiose but I mean it and I hope you’ll read through to the end and choose to take one small, totally free action, that will change your life and likely those of others.

On September 10th of this year I spent an entire day in California State Prison with people who had committed felonies and worked with them on business plans to help them create legal enterprise upon their release as part of Defy Ventures 6-month training program.

I hadn’t cried this much maybe since childhood. Not cries out of pity but out of joy, pride and sadness at the lost lives, broken families and a broken system but also at the hope, ambition and remorse that I witnessed. I wasn’t verklempt — I wept.

I hadn’t felt this human since the day my two sons were born. I felt a deeper connection with human beings than I have felt in many years. I gave myself to help others but it was clear that the prisoners gave me as much as I offered. They showed vulnerability and a genuine interest in learning.

I sat standing 1 foot away from somebody who’s been in prison for 15 years of his life and I had 60 seconds to open up to him about something that causes me pain in my life while he stairs into my eyes I found myself going deeper than I would with even friends or family.

How could I not? Similar men had just gotten done telling me about their own childhoods. They told me of losing fathers at 3, of moms on drugs, of uncles that asked them to hold guns to cover them at 8. Grown men, prisoners, with huge muscles and tattoos everywhere cried and told me stories. And they didn’t want pity. They wanted opportunity. They wanted to learn.

Defy Ventures is a program that aims to educate people in prison to become better humans upon graduation. They offer classes in personal responsibility and accountability, they teach men to forgive themselves and to forgive the people who perpetrated them as children because they all grew up surrounded by bad influences. Defy teaches them to love themselves and their fellow man but also to love and respect their families.

Defy teaches them personal finance like how to keep a checking account, the difference between debt and equity, what cashflow is and so forth. And then Defy encourages every member to create a business plan for a business that they can launch upon release with an emphasis on tangible businesses that can be cashflow positive in just 3 months.

Defy Ventures runs business plan competitions and has people like us who attend and give business advice and feedback. You can go. You SHOULD go. Here is how. You can make excuses — many do. But if you commit one simple day of your life I literally promise you that you will email or Tweet me a “thank you” and tell me you’ve been moved. I know because I went back a second time with 75 or so tech executives and VCs and my inbox is flooded this morning.

Catherine (Cat) Hoke founded the program in 2010 and launched the business plan competition in 2012. You can read more about her here but let me give you my take. I think my personal branding is one of not offering false praise. I don’t sugar coat and I don’t make people artificially feel nice by saying how AMAZING they are. It’s just not me. I don’t try to be mean but I value directness and integrity when I offer praise. So here it is

Catherine Hoke is the most inspirational person I’ve ever met

Why Cat?

She works as hard and is as committed as any of you founders or VCs out there and she’s absolutely crushing it on impact and results and the better she does — there is no upside for her. She runs a 501c3 (non profit).

When she talks in prison she commands the respect of every person in the room — and you’re obviously talking about some pretty hard individuals. When she stands in front of executives she doesn’t cater to us. I’m sure she appreciates us but she’s not there to kowtow. We are on a level playing field with the EITs. And I watched her get up in the grills of people who are convicted of serious crimes and get them to confront their anger, frustrations and fears. I watched her when the graduates met their family members and you can see that the “everything” to her is the bond between incarcerated men and their children and wives.

As Cat says, “the best way to keep these men from coming back to prison is to find a way for them to earn legal dollars.” And as I’m sure you know the system isn’t exactly hospitable to employing ex-felons so the best way to sustain them is to find self employment and for them to hire each other. And the results?

  • Defy Ventures graduates have a 3.2% recidivism rate (the rate at which they are re-incarcerated) against a national 5-year average of more than 75%. The 3-year recidivism rate in California for comparison is more than 50%.
  • Defy has graduated 1,100 prisoners upon release who have created 150 businesses that now employe 350 people — many of them ex Defy Graduates

And of course Defy has a post-release program to help with reentry into a society not geared towards helping with recovery. They charge alumni $100 / month to stay in the program to make sure they have real skin in the game.

I this all sounds like psycho-babble but I promise you that if you’ll commit just one day of your life to go to prison with the team at Defy Ventures you will feel profoundly moved, you will feel deeply human and you will feel the calling to do more. It will shred every perception you have about convicted felons and the penal system in the US. It’s not that these men aren’t guilty — they are — but that the system is biased towards over-incarceration and sentencing to people of color and has a byzantine set of rules that often elongate the sentencing of those who don’t have resources to fight them.

And leaving aside the penal system you probably have pre-conceived ideas of what it would be like to sit and talk with somebody who has committed armed robbery, been in a gang or even committed a violent crime. I went in feeling intimidated to be in a room with these men. By the end of the day I was eating pizza at the same table as them asking them questions about their lives and they of mine.

There is literally no way for me to describe this — you just have to experience it. You forget they are prisoners and realize they are men who have done bad things and made mistakes — many of them as teens. You forget you’re in a maximum security prison. You lose all fear and inhibition and even find yourself pushing yourself to be more open. I know this will happen because I’ve now watched it on two occasions with more than 100 tech executives.

I watched tough men melt as they made commitments to their children and wives upon their graduation ceremony.

I watched this man who has been incarcerated for 20-or-so years get down on his knees and re-propose to his wife and promised her to be a better man and stay true to the Defy mission upon graduation. No: There was not a try eye in the room — inmate, business executive or family member.

I watched a man who had a 9-year old struggle to tell her that he loved her and that she was smart to her face. He kept telling the audience but struggled to tell her directly. Cat was having none of it. She went to him, asked him to look in her eyes and tell her directly and he did. But nobody ever told him to his eyes that he was good or loved and so it literally wasn’t an experience he knew how to deal with.

Anybody who has been on a Defy trip know the drill. You get in a line with executives on one side and EITs (entrepreneurs in training) on the other. Cat hates calling them “inmates” or “prisoners” or “convicts” or any other label that emphasizes the worst things they’ve done in their lives and wants them to see possibility in their futures.

She asks you to “step to the line” when a statement made about you is true or back from the line when it’s not.

  • How many of you were raised with 2 parents?
  • How many of you had violence in the home?
  • How many of you lost an immediate family member before the age of 18?
  • How many of you finished high school?

Of course the contrasts are stark and the questions get more personal and much harder to hide from the privilege our side of the so obviously enjoys.

  • How many of you were suspended from school ever?
  • How many of you committed an act for which you could have been arrested — whether you actually were or not?

On that question nearly every person is at the line. The difference? On our side if you were truly busted for a “stupid childhood indiscretion” you simply hire lawyers to get out of situation with a hand-slap unless it was truly a heinous act. Oh, wait. Even those have a price in our society … Brock Turner raped an unconscious woman and was released in 3 months. Can you really say we wouldn’t have thrown away the key on a poor African American or Latino who wasn’t a white, Stanford swimmer?

What Tangible Thing Can YOU Do?

Go to prison with Defy Ventures. The rest will just happen. And you will never see our society in the same light.

I met Catherine several years ago at the request of my good friend and colleague Mike Su. He kept telling me how profound this prison program was and would I meet Cat. Yeah, yeah, whatever Mike. Sure, I’ll meet her.

We met. She was smart (she started her career in private equity!) and ambitious and wanted to “save the world” but who didn’t. Everybody I meet seems to say that and have some sort of angle for making the world a better place. I sounded great but it was one other to do for me “some day.”

Mike didn’t let up. He asked and asked and asked until I ran out of excuses and I met Cat again and agree to come. Honestly, Mike is a mensch and never gave me a hard time and also never gave up on me.

So I went.

And I will never be the same. It’s that simple. I got as much as a gave.

Mike — Thank you (he’s the tall guy standing next to me)

And I’m a huge believer that “a few people can make a really big difference” and start a snowball effect. So I committed to going back again and partnered with Brad Feld to bring a team of 75 entrepreneurs and VCs to do it with us.

And my hope that as Mike brought me and I brought others that we can now create a snowball effect where every person in our industry makes a trip to prison. If we can experience the system we can begin to fix the system. Until then it’s theoretical.

Brad and I had such a positive experience that we’ve committed to now leading a delegation of VC and tech executives in the Bay Area as soon as we can coordinate it. I’ve given my time and my money but I know I can do more.

I am committed to finding ways to help graduates get jobs. I have my first candidate who gets out in a few months. I was touched by his story and his family. They are Chinese immigrants and as he said directly,

“They gave me every opportunity to succeed. I wasn’t raised badly — I was well educated. I made a mistake when I was 19. I was with the wrong crowd. And I’ve paid dearly with the last 13 years of my life. I will never be back here again and Defy gave me the confidence to believe in myself.

You know what else he said? In front of the entire crowd?

A month ago I had a group of executives in here teaching interviewing skills. One guy was particularly harsh on me — but I could take it. I’m used to harsh. 30 minutes later he came up to me and told me he was thinking about our discussion and I have a couple of other ideas for you. Why don’t you try a, b and c

And then he paused and his voice quavered.

It was the first time in 13 years that anybody other than my family had actually spent 30 minutes thinking about my well being. It was the first time in 13 years that I truly felt human. Defy Ventures has given me my humanity back.

And it will do the same for you. Please take that small action. Attend. It’s free. Don’t worry whether you’re “qualified enough” — most of the ideas are about building businesses in landscaping, car detailing or graphics design — all businesses designed to cashflow. And I promise you that you’re qualified to have an opinion on these things.

And by the way — you’ll also become kindred spirits with the execs who go on your trip so there’s that benefit, too.

The winner of my first visit?

This amazingly passionate man who has been incarcerated 20+ years. He has a business that will provide sanitation services to clean your public garbage & recycling bins. He had graphic boards showing the designs of the trucks, knew his target markets and he stated goal was

To be the most successful Defy Ventures graduate in the history of the program so I can employ the most number of Defy graduates and give back to this community that has literally changed my life.


On our most recent tour Caroline Fairchild from LinkedIn attended. I promised her I would write about this experience for the LinkedIn platform so I didn’t write about yesterday’s trip here. I will write about that as soon as Caroline is ready.

(Cross-posted @ Both Sides of the Table)

Oracle in the cloud: The analyst conversation


Wavebreak Media LTD

Last month, Oracle presented OpenWorld, its annual confab of enterprise software, in San Francisco. OpenWorld gives Oracle the opportunity to showcase the latest technology, products, and future directions of this huge company. It also creates a nexus of customers, prospects, press, and analysts who converge to study the company and its plans.

As part of the CXOTALK series of interviews with leaders, I invited three important analysts to examine Oracle and read between the lines of what the company said. Part of this mandate included looking at Oracle’s position in the market relative to important competitors.

The three analysts who participated in this session are:

All three are known as astute and trustworthy observers of the enterprise software market.

The analyst conversation converged on the idea that Oracle is all-in on the cloud as a technology, product, and service platform. For this transition, the question is not Oracle’s engineering ability, but whether they have a business model to compete with native IaaS and PaaS players, in particular, Amazon Web Services. For example, can Oracle match Amazon’s cadence of price cuts to remain competitive with AWS?

We also discussed why Larry Ellison, Oracle’s founder and CTO, pushed so hard on Workday yet hardly mentioned historical competitor SAP. Louis Columbus hypothesizes it is because Workday’s potential addressable market is extremely large and Ellison wants to draw attention to growth in the cloud opportunity rather than to the large, existing on-premise business, which will inevitably decline over time.

It’s worth noting here that Oracle’s overall 2016 revenue was $37 billion while its SaaS and PaaS revenue rose 82% in Q1 to a run rate of almost $4 billion. Although cloud remains a small part of Oracle’s current revenue, it is clearly the future. [Source: Mark Hurd discussion at OpenWorld.]

At the conclusion, the analysts offer specific advice to CIOs and Oracle customers.

To summarize the in-depth conversation, we created a special short video and transcript, which are embedded above. You can also watch the entire episode and read a complete transcript.

Michael Krigsman: One of the interesting things at OpenWorld, they really leaned heavily on their competition with Workday, and pretty much just dismissed SAP as a contender at all. So what’s that about?

Louis Columbus:

I think it’s a total available market issue. I mean, to your point earlier, these are very, very sharp people and of course, Larry knows exactly what he’s doing. The total available market of Workday is 10x what our salesforce is right now. So, it’s a very attractive target, and positioning against them relative to SAP is completely understandable. I mean, SAP clearly has a strong ERP base, has done fine with a variety of its acquisitions, however, it’s not nearly as attractive as a cloud-based company making headway in a market with a 10x market-sized multiple than other competitors that have gone down the path. So really, he’s signaling, “There’s a total available market pool, this is a great profit pool and I want a part of it.” I think that’s what he’s really saying.

Michael Krigsman: They’re saying that the Workday-addressable market is better than the SAP-addressable market? I mean, is that the point or am I missing something?

Louis Columbus:

It shows potential for growth, whereas the SAP market doesn’t. I don’t think that Larry wants to take a high profile event and go into the trenches of how they win and lose deals every day against SAP on their core business, core functionality around ERP. I mean, that’s probably where they face a majority of competition. SAP’s efforts into the cloud had been sometimes strong, sometimes weak. They’re not a poster child of exceptional cloud competitiveness and strength. He’s further ahead, looking at Workday and saying, “How do I position against HCM there?” That’s a growing market. The total available market is much larger; the compound annual growth rate is greater. They’re dealing with customers who believe in the cloud at the enterprise level, to Larry’s point that the CIO believes that. And, I think, to Larry’s point, the heterogeneity of technology stacks is driven by the decision-makers: CMO, Chief of Marketing, is going to go, “That is a great analytical tool, I’m going to need that to be able to manage my pipeline or to quantify my value as a business unit,” relative to the CIO saying, “I need a business consistency.”

Yeah, and back to your point: I think that that’s what’s going on. I think that’s just a prime base. It’s an enterprise that believes in the cloud, it can go to hundreds and thousands of seeds easily, plays exactly to where he wants to go with his revenue model.

Larry Dignan:

Don’t forget the narrative, right? These conferences are about a narrative. They always are. So, you know, the narrative for Oracle, “It’s cloud,” they’re innovating. Two words, that’s what they’re tryin g to project. So, if you come out and you start yappin’ about SAP, well, it’s like reading a sports story from ten years ago. We’ve all heard it over and over again, right? You know how it’s turned out, how it will turn out, whatever. But it’s an old story. And that’s why you see Larry Ellison going off about AWS, right? Because Workday arguments get a little tired, right? I mean, I see Workday, Oracle, I’m thinking apples and oranges. I mean, they compete in the same space in HCM, and ultimately financials, but it’s a different kind of company that they go after.

Michael Fauscette:

But I think that supports the idea of its position as much as it is anything else. It is in fact the right opponent at the right time, and the story against SAP, you’re right. It’s over. So I want to tell an exciting new story that sets me in the markets, in the focus, in the way I want to be seen. And that perception shapes a lot of people’s reality.

Michael Krigsman: So the narrative, as Larry Dignan was saying.

Louis, do you want to share some thoughts on this infrastructure strategy, which was so prevalent, so powerful at OpenWorld?

Louis Columbus:

I think there’s two really critical pivot points for them on this whole infrastructure strategy. First of all, can they innovate at the speed of Amazon? Arguably, yes. Oracle is a powerhouse Silicon engineering center company. So yeah, could they match them on pure patent production? Sure. And there are plenty of engineers there who would love to rack up a hundred patents in their career by going after Amazon. So that’s a pretty compelling value proposition.

The issue is, can the culture of Oracle engineering sustain the kind of culture that Amazon has right now in terms of a market leadership position and the way that engineers get their work at Amazon. So, can they pace on innovation? Sure. I mean, they’ve got to win a patent war somewhere, they’ve got to rack up a couple hundred patents really fast, and Oracle has the ability to do that.

Can they match the cadence of price cuts of Amazon? That’s a completely different story because while they do have that great revenue stream coming off their database business, matching the cadence of the price cuts of Amazon? Really hard to do, and stay profitable and still grow; and balance that, balance that with building apps that make money. So you’ve got this triad of factors that they have to keep in balance: drive a profitable applications business as they transition to cloud, be able to deal with the cadence of innovation of a competitor that has attracted world class engineers daily, and then third, being able to deal with the touring pace of price reduction. So yeah, it can be done. But will it be done in the short term? Probably not.

Michael Krigsman: Larry Dignan, what about the question that Louis raised of the ability of Oracle to keep undercutting Amazon? They’re both very large companies, so what about that?

Larry Dignan:

There are some things with Oracle’s AWS fascination that kind of boggle the mind a bit. A. just on margin, that Infrastructure as a Service business? It’s challenging, right? So my guess is, you know if you read Clay Christensen, you kind of see that slide where Toyota started down here, and the established players, in this case Detroit, kept moving up and up the stack, and then eventually the players at the bottom were also there too. I think that’s what this is about, because the biggest takeaway I had watching Ellison’s keynote is that yes, AWS must be taking database workloads from Oracle, otherwise Oracle will not be trying to punch them in the face. So, when they talk about their databases, their AWS databases not being as open, AWS being harder to move from, there may be some element of truth in that, but the bottom line is AWS made that stuff very easy to consume. And, that’s a hurdle.

So, I think from Oracle’s strategic point of view, they need the infrastructure piece because they need to sell you on the platforms and ultimately the applications, because that’s where the money is.

Michael Krigsman: So it’s the fuller scope, so it’s the infrastructure that’s the fuller scope of the suite.

Larry Dignan:

Right. And Oracle can’t lose infrastructure because once you’re in AWS, you’re probably going to buy higher level services. And, there’s not question that AWS is moving up that stack, they’re moving up that value prop, and that’s showing up in database workloads. So, if all these databases run around and they have this server-less infrastructure, and all that, then … So the real race is, you’re going to be buying business functions in the future.

Mike Fauscette:

But, we’re not moving to a world where one vendor’s going to own everything. It’s a world in the cloud where you’re going to have to see a lot of peaceful coexistence, you’re going to see a lot of openness. And it’s something they’re not quite… and no vendor from the old world to the new wants to accept that, but that’s just the world that the cloud is leading to.

Michael Krigsman: And, Larry Dignan, your final thoughts and advice for CIOs.

Larry Dignan:

I mean, I think any tech buyer is going to play ball with Oracle. And if you’re an existing customer, trading up in the cloud might totally work well for you. You’re going to get bundled deals, and yeah, a CIOs got to look at Oracle just as they would any other vendor.

Michael Krigsman: And Louis Columbus, you’re going to get the final word here.

Louis Columbus:

Ok, well I appreciate it. Well, my advice to CIOs is: use this ambition from Oracle to your advantage and push them to bundle in everything you possibly can. If you’re looking at a suite refresh, push for that. If you’re in an audit, threaten to leave and move your database loads to AWS and watch the audit probably drop. But you know, play hardball, because the ball’s in your court as a buyer now. Competition’s a beautiful thing, and competition brings out the best there is to offer, I think, from all these people. And I think you can look at beginning to reduce even maintenance fees, if you’re a CIO. And, in other words, Oracle’s hungry to build out this stack on the cloud, and use AWS pricing as a barometer in your negotiations with them. So, you’re in a buyer’s market. You’re in a great position, so make the most of it. And go cut a great deal with them.

Oracle is a client and paid my expenses to attend OpenWorld. Thank you to my CXOTALK colleague, Lisbeth Shaw, for assistance with this post.

(Cross-posted @ ZDNet | Beyond IT Failure Blog)

Venture Capital is About Human Capital

Gregg Johnson, CEO of Invoca

For the first 5 years or so after I became a VC I didn’t talk much about what I thought a VC should be excellent at since frankly I wasn’t sure. I was mostly doing my job and trying to figure out how to be better every day.

After a decade on the job I’ve started to speak more openly when newer industry colleagues now ask me what I’ve learned.

The number one advice I give is “stop trying to be too smart”. Most VCs did well academically and had enough career success that a venture firm was willing to give them an investment role or they were able to raise their own fund. It’s easy to think the role of a VC is to have strong opinions about markets, trends, tech dynamics and so forth. We think we’re supposed to act smart and have insights that others don’t possess.

I don’t think this is the job.

Entrepreneurs are supposed to have insights that others don’t have and we’re supposed to be good judges about which entrepreneurs and executives have both the most clever ideas and the right skill sets to do transformational things against all odds.

So I tell people we’re fundamentally in the people business. Our core skill is being able to identify talent and how to persuade the most talented people with whom we have access that we would be valuable to work with. We then help surround founders with other talent who want to join important causes but don’t have the startup idea themselves. We help founders through difficult moments, we help coach, we act as sparring partners, we help them resolve conflicts when they’re fighting with co-founders and we help them deal with adversity as well as successes.

That’s why I often say

The role of VC is “chief psychologist.”

We might help a management team deal with a vexing strategic question or a thorny negotiation but these are mostly tactical. The biggest difference we can make is helping support talented teams with complementary talent. Think about how profound a difference adding Sheryl Sandberg early at Facebook was to Mark Zuckerberg and knowing that he should stay in charge of product and strategy while she ran operations.

Fundamentally venture capital is about human capital.

The role of VC is sparring partner. The role is to challenge the thinking precisely because we get a bird’s eye view across many situations and many of us have been in the driver’s seat ourselves in our younger days.

And as a VC I often cultivate relationships with the most talented people with whom I’ve worked over the years and look for opportunities to work with them again. It’s rare to find extraordinarily talented individuals who are natural leaders and who are driven to succeed and who have a passion for startups so when you do you work hard to find opportunities for them.

Today I couldn’t be more delighted to tell you about one such individual — Gregg Johnson — who just left after 10 years to come and be the CEO of Invoca, a company I proudly backed.

Gregg and I worked together at Salesforce more than a decade ago. Gregg was a graduate of Stanford and a Wharton MBA and had worked at the consulting firm BCG so I knew he was smart and capable. But what I noticed about my time with Gregg was how quickly he turned thoughts into actions. I noticed that team members naturally gravitated to him because he was a doer more than a pontificator. And in an industry of sharp-elbows he is amongst the most likable people I know.

So when I left and became a VC I stayed in close touch with Gregg and he was on my very short list to hopefully work with again one day. The rest of our team included the founding CTO of Maker Studios (Ryan Lissack) and the CEO of DataSift (Tim Barker) so we seemed to all be in good company of ex Salesforce execs looking to make a difference.

But Gregg stayed and grew and took on more responsibilities and became a senior member of Salesforce’s Marketing Cloud team. I think he wanted a meaty role if he was going to leave and finally we had something compelling.

Invoca has grown its enterprise customer base 550% in the past three years including major customers like Microsoft, Allstate and SunTrust. It has grown recurring revenue by more than 500% and deal-size by 276%. Importantly, we recently announced a $30 million financing that gives us the resources we need to build a global enterprise software company.

For years I struggled to convince people that phone calls mattered. While everybody was infatuated with the “truthy” belief that in the future nobody will make calls as we all interact with AI chatbots, the volume of calls has exploded with inbound calls to businesses skyrocketing to nearly 170 billion per year over the next few years.

The explosion of mobile phones has led to a boom in inbound click-to-call traffic that has proven to convert at a higher close rate and increase average-order-value over web-only sales & marketing. For some of my more skeptical portfolio companies I simply asked them to run a trial of inbound sales calls and they were shocked. For some companies it is now > 70% of the deals they’re closing and they’ve seen it as their secret weapon.

Marketing departments, software partners and investors have now woken up to this opportunity.

The existing Invoca team has been in place and functioning incredibly well the last few years and I’m so honored that Gregg has decided to come on board and help lead us to the next level.

I have often said that “a few key people make all the difference in any company — no matter how big or small” and that is my core principle as a VC. I can try to be as smart as possible on market trends, industry dynamics and so forth.

In the end I know the only true differentiator in venture capital is the company you keep. It’s the people who want to work with you. It’s the founders who are willing to let you join their boards. It’s the executives who trust you to join the early-stage startups you’ve funded. It’s the executives at bigger companies who trust you and are willing to partner with the startups you’ve backed because they know your word is good.

Venture Capital is a people business. Nothing fancier. And the real talent are the teams on the field.

(Cross-posted @ Both Sides of the Table)

Why I Backed a 24-Year-Old Trying to Assess Human Potential

Last week Upfront Ventures announced backing Rebecca Kantar’s startup Imbellus, a company designed to assess human potential and ultimately change the way we teach children. We led a $4 million investment along with Thrive Capital, GLG and Sound Ventures.

The news blogs  covered the what, how and how much but I want to focus on the “why” and try to be instructive of what I think makes for a great A-round startup.

I speak a lot on college campuses and entrepreneur events and amongst the most common things I’m asked to talk about are:

  • What do VCs fund?
  • How does one come up with the right idea to start a company?
  • Do VCs really take risks on ground-breaking ideas any longer or do they just fund businesses once there is proof of traction?

I have standard answers to all of these questions at least as far as my personal funding preference are concerned.

Hard Problems

I encourage entrepreneurs to try and tackle harder problems even if it makes fund raising more difficult and is less likely to succeed. As entrepreneurs many people are driven to solve their personal issues right in front of them, which leads a disproportionate number of founders to focus on: music, bars, restaurants, photos, etc.

There is nothing wrong with focusing on these if you’re passionate but know that you have a large set of competitors and industries in which it’s hard to eke out a meaningful business.

Mission Driven

I also am looking for founders that are on a personal mission to solve a big problem. I know that “mission driven” sounds nebulous or some convenient definition of anything we want to fund. But really it’s something I look for. It’s actually very easy to spot when a founder has decided to focus on a concept because he or she has “spotted an opening in the market” or building a derivative business that is “Uber for X” or “Airbnb for Y” or “Dropbox for Z.”

There’s nothing wrong with these businesses but as a VC you tend to see 5 similar ideas all at the same time and knowing that it’s going to just come down to who executes the best it’s hard to pull the trigger on a A-round until you have more data on who’s winning.

Building any business is hard, all-consuming, frustrating and fraught with personal challenges. When a founder is “opportunity driven” it’s too easy to quit at the first bump in the road. When a founder is “mission driven” you get the sense that he or she will do whatever it takes to make an impact in the market they serve and will keep persevering whatever the startup trends of the month.

70% Team, 30% Market

I also talk often about how much the team plays a critical role in my decision backing an A-round company because so much changes as a company develops. Incumbents launch products, VCs throw cash at other competitors, team members quit, the economy dips — whatever. But only truly talented entrepreneurs show the grit required to respond rapidly to a changing environment. When you think about great companies that have survived market changes or platform changes you think about Facebook, Snapchat, Uber and the like and have to respect their great ability to constantly adapt.

So Why Imbellus?

When I first met with Rebecca Kantar I was stunned with the wide scope of her vision for building a company. Her mission was vast: She wanted to change the way we teach children in America. But she had such concrete plans for the 10+ years that it would take to build towards her goal.

She highlighted for me how we measure human potential today and it’s based on the workforce that existing post WWII where teaching rote memorization of facts: Math, reading comprehension, writing, basic science, etc. was sufficient for the jobs that existed in the industrial economy. We assessed skills by standardized tests designed to assess competency in this basic knowledge and this persisted in both the workplace interview environment as well as how we admit students into colleges.

Inevitably as a society we began “teaching to the tests” and we design curricula around proficiency in these basic skills.

But we of course now live in a “knowledge economy” that has to constantly adapt to changing market conditions. As leaders we intuitively know that while basic skills in math, science, reading & writing are necessary — they are not sufficient.

As leaders we know that to succeed in today’s economy we need people who possess abilities to deal with large volumes of information and cut through the clutter to get to what’s important. We need leaders who can rigorously prioritize. We need leaders who can deal with a vague set of inputs and rationalize decision matrices. We need leaders who know how to accomplish feats through teamwork and collaboration. We need people who have emotional intelligence as well as actual fact-based knowledge.

Fundamentally the system feels broken. We educate and train and test for a set of skills designed to succeed in 1950.

Imbellus is designing systems to assess how candidates analyze information, develop ideas, make decisions and solve problems that aren’t based on rote memorization of facts. There aren’t necessarily right or wrong answers and each company may index differently for how its employees need to score across various dimensions to succeed in that particular organization or job functions.

The systems they are building are adaptive and computer generated so they can’t be studied, memorized or gamed.

It is a super early-stage company so over time we’ll reveal more about the methods, systems and types of assessments we’re building.

But what was clear to me in backing Rebecca was that I was getting behind somebody who has unbridled ambition is mission-driven and has a differentiated plan for how to solve a problem that we all know exists but feels intractable.

Truly, in many ways, my concern was the inverse of normal business pitches. My only concern was whether we could limit Rebecca’s scope of work enough to focus on shorter-term, more tangible problems that could lead to a business before the mission. Luckily Rebecca herself is highly adaptive and was able to rigorously prioritize which problems to solve first. Invariably she would no doubt score very highly on her own assessment tests.

It’s rare that I feel so inspired by one entrepreneur and his or her vision. Rebecca is truly unique and I can’t wait to see what she and her team at Imbellus deliver over the coming years. It obviously takes an entire team to build and execute against such an ambitious project. Wishing all of Team Imbellus much success in your journey.

(Cross-posted @ Both Sides of the Table)

How Do VCs Choose Their Investors (and should entrepreneurs care?)

captureI recently read a blog post by Beezer Clarkson, Managing Director of Sapphire Ventures about why entrepreneurs should care about from whom their VC funds raise their capital.

I spent a bunch of time thinking about this position — especially since Beezer is an investor in Upfront Ventures. There are a lot of things I think entrepreneurs should care about when raising from a VC:

  • How big or small their fund is?
  • What percentage of their fund will you be?
  • How much money will they reserve from their fund for future investments in your startup?
  • How much pull that investment professional has within his or her fund? (which matters for getting future support)
  • Where the fund is in its investment cycle (year 1 out of 10 or year 7 out of 10)?
  • How much experience they have in your sector?

I could go on for a long time. Maybe I’ll save that for a future post. But should entrepreneurs really care whom the LPs of a fund are? I’m still not sure.

But I do know that VCs should care a great deal about whom their LPs are and I find that some are less thoughtful than they could or should be. We were in the very fortunate position of having more than $425 million in commitments for our last fund, which only raised $280 million. We capped our fund size so that we would stay true to our investment strategy in terms of size, scope and number of partners as we stood in 2014 when we raised the fund.

And we felt terrible not being able to let every LP in but we were forced to make some hard compromises yet we opened up our fund to Sapphire even though they were a first time LP.


1. Truly Focused on VC / Knowledgeable About How Partnerships Work

One of the things I value in an LP is a really passionate and inside knowledge of the venture capital industry. There are many LPs who invest in VC one day, oil & gas the next and timber on Wednesday. I’ve met many smart and capable people like this but it was also clear that many of them didn’t have an intimate knowledge of what is truly unique to venture.

Beezer did. She has formerly worked at a VC fund (DFJ) and worked closely with the partners and the network at DFJ and knew what it was like to build, manage and evolve a VC partnership. So I immediately felt like I had a partner whom I could call for sensitive advice on topics where there aren’t many sources of input or mentorship. It’s the same reason I think many entrepreneurs like working with VCs who had formerly been entrepreneurs.

2. Help with Hard-to-Access People

Of course I also appreciate the fact that with Sapphire came better access to the executive team at SAP, including organizing a small dinner with their CEO so I could learn first hand where they see the future going. We have many LPs who come from industry and this is truly a value-add in a LP/VC relationship

3. Stable Capital

Amongst the hardest things to find when one raises a new fund is ability to have stable capital. Many of the sources of capital for new funds come from investors who can’t necessarily back you in good times and bad.

We lived that first hand. Our first LPs from 1996 were industry players who put us in business: Carrefour (the large European retailer), DLJ (the former investment bank) and a billionaire software exec. As venture fell out of favor all three pulled out of the asset class. Even though our 2000 fund was the single best performing fund in the United States for that vintage, continuing to get investments wasn’t possible so we had to rebuild.

We rebuilt our base and secured what we thought was the perfect anchor only to find out that a strategy change for the firm meant our lead was moving from VC to timber and they pulled out of VC altogether. This was in 2010 — exactly the wrong time to be pulling out of venture.

So you really want LPs who invest in the category in good markets and bad. And as a VC you still need to earn the right to get allocations when you raise new funds but that’s within your control.

Many VCs have turned to Foundations and University Endowments (F&Es) as a source of stable capital and this has certainly been a strong pillar for many a VC fund. We ourselves decided to build > 35% of our fund with F&Es.

What’s interesting about Sapphire is that they have now raised on an “evergreen structure” with $1 billion new fund (across LP investing and direct investing into portfolio). So we see them with the same long-term eye as we would our other sources of capital.


Should entrepreneurs care that we have Sapphire as an LP? Well — only in so much as we have an easier time than others in getting technology entrepreneurs in front of executives at SAP when appropriate.

But to other VCs — when you go to raise money — we’ve been thrilled with our choice to work with Sapphire. They’ve been a great partner, delivered on what they said they would do and working with Beezer has felt like working with any other VC I work with. She knows our business and often acts like an entrepreneur herself.

For that — I’m grateful. Congrats on your new fund, Beezer and Nino. And thank you for having the conviction to back Upfront.

(Cross-posted @ Both Sides of the Table)

​#CXOTALK Reinventing the legal industry with AI, machine learning, and augmented reality

#CXOTALK Reinventing the legal industry with AI, machine learning, and augmented reality

Image from iStockphoto

The legal industry has a reputation for being slow to change and behind the curve on adopting new technologies. A credible survey of law firms in the UK indicated these facts:

  • 17 percent of partners in the top 25 UK law firms are women
  • 80 percent of the law firms surveyed see digital strategy as critical
  • 23 percent have made corresponding operational changes
  • 95 percent are planning major IT projects to improve efficiency

These numbers paint the picture of a backward-facing industry focused on efficiency at the expense of innovation. A study of the legal industry by Georgetown University [PDF download] concludes:

Since 2008, the market has changed in fundamental ways. Not only has demand growth slowed dramatically, but the competitive dynamics of the market have shifted as well. Clients who once deferred to their outside law firms on all key decisions impacting the legal services they purchased no longer do so. Instead, clients increasingly demand that outside counsel offer more efficient services with more transparency into both work processes and costs. Clients are also more prepared than ever before to disaggregate matters, to retain work in-house, and to bring in additional (even non-traditional) service providers.

In other words, law firms must respond to the changing demands of consumers just as companies do in other industries. For this reason, digital transformation is coming to the legal industry.

For episode 188 of the CXOTALK interview series, which invites people shaping our world to discuss their experience with digital transformation, I spoke with Michael Shea, CIO of Morgan Lewis, one of the largest law firms in existence. With over 2000 legal professionals and two billion dollars in revenue, Morgan Lewis is a true multinational organization.

The discussion with Shea centered on how law firms can use technology to drive innovation in addition to improving efficiency. In a comment that echoes the Georgetown report mentioned earlier, Shea explains:

Lots of new technologies that are coming onto the market that will have a significant impact on how law firms operate in the next five to 10 years. Firms that are investing in these new capabilities and adopting change will gain competitive advantage. Those firms that adopt and change and innovate will be the haves and the have-nots in the industry.

Our in-depth, 45-minute conversation explores the role of technology in helping Morgan Lewis remain competitive in this changing field. Of equal importance, creating the right workplace is essential to helping the firm attract and retain senior partners and younger Millennial workers.

In the short clip embedded above, Shea explains why the firm invests in knowledge management, artificial intelligence, machine learning, and augmented reality. The answers go far beyond efficiency alone and get to the core of innovation and remaining competitive as a global player.

CXOTALK brings together business leaders shaping our world for in-depth and personal conversation. Please watch the entire episode and read the complete transcript. Thank you to Avanade for being our sponsor.

(Cross-posted @ ZDNet | Beyond IT Failure Blog)

What to Make of Andreessen Horowitz’s Returns?


Rolfe Winkler wrote a piece in the WSJ about A16Z’s returns in which he says they “lag behind Sequoia, Benchmark and Founders Fund.”

Scott Kupor of A16Z responded with a comprehensive overview of valuation methodology in a post that while accurate feels more targeted at sophisticated Limited Partners (LPs) who invest in funds.

Let me offer you an insider’s take. VCs strangely never seem to weigh in on other VC funds. I have no incentive to do so other than to help those reading the WSJ piece better understand how I believe most insiders think. As an entrepreneur I never really knew what to make of VC return data. Now from Both Sides of the Table I know a thing or two.

When Andreessen Horowitz as a fund first started the industry went from “We love Ben and Marc” to “they raised how much?” to “holy fuck, they paidWHAT for that deal I tried to get into?” to “Jeez — they sure are hiring a ton of staff. Can that really work?” to “How can we hire more staff to keep up with the services they offer?”

In short, the VC industry is very sharp-elbowed amongst some very competitive people who are used to winning and most deals don’t have enough space to share investment rounds so people were naturally pretty quick to judge A16Z.

The word on the street now is that A16Z is truly a force to be reckoned with and has done a lot to change the dynamics in our industry. Having a huge services venture firm isn’t for everybody and it isn’t the only strategy that can succeed. But privately now most VCs I know contend that it has gone much better than they had initially expected.

There is obviously room for different types of firms / approaches that can be successful. Case in point: Benchmark, USV, Foundry Group and a ton of other great firms maintain the really small organization model.

Here’s what I know:

  • Most entrepreneurs I know would love to work with A16Z. They perceive it as a place that is well connected and very helpful given the level of services they provide.
  • Upfront Ventures has partnered with Andreessen Horowitz on several deals. In some they have large sums of money and others they have small checks. But in each case I would work with them again. Why? Simple: it is value-added for both entrepreneur and co-investor. I obviously benefit if a co-investor on a deal I’m involved with helps with introductions, recruiting and so forth. Especially in an industry where so many investors do so little to actually help.

But, Mark, that’s not the point. What about those RETURNS the WSJ article spoke of?

Ok. First, the returns data Rolfe has shown are actually pretty damn good. I know tons of LPs in A16Z and I haven’t heard any complaining. Even when they are off-the-record with nobody else listening.

But more importantly, VC returns are notoriously hard to measure at one point in time. Why? In the article it talks about Sequoia’s $19 billion sale of WhatsApp to Facebook that generated apparently $3 billion for Sequoia and its shareholders. It claims that this is more than Andreessen has returned across all of its funds. But let’s be honest — this is more than much of our industry has returned. This was an industry defining deal on returns in the league of Google, Facebook, Twitter and one imagines Uber.


The day before the deal was struck it’s very possible that Sequoia could have held the total value of the WhatApp deal at $1.5 billion (and their stake worth $237 million not $3 billion) — the reported value at which they invested in the last round. Why? Because VCs tend to “mark to market” for private investments so you would often value a company based on the last financing. If a company has significant revenue you might value it based on some industry multiples but WhatsApp had very limited revenue.

So literally the day before the Facebook acquisition Sequoia’s fund could have been significantly less valuable on paper. Now — I’m not saying it wasn’t already a spectacular fund — I believe Sequoia is the best VC in the industry in terms of consistently amazing returns.

But I’m making the opposite point. A16Z could be sitting on several deals that could be worth 15x what they are today. Or not. We can’t know.

So. What’s an LP to do in deciding which funds to invest in?

LPs decide based on a variety of factors but it boils down to some version of:

  • Ability to source the highest quality deals that will become valuable
  • Ability to win competitively when multiple VCs compete
  • Quality of investment partners and likelihood that they are going to work hard (and play well together) for the next fund
  • A proven track record of delivering results

In essence they’re investing in a firm’s potential. Consider that Accel had been a great fund and then post dot-com crash some were questioning whether they had lost their way. So some LPs pulled out. And then they closed their next fund that invested in Facebook at its A-round and that fund must be one of the best performing in history. Whoops!

See. Great firms can have consistently great returns and then for whatever reason one less good fund and then another spectacular one. And Accel has gone on to attract a deep bench of fantastic investment partners and many LPs would fight to get into their funds.

So LPs are investing in potential. Does A16Z attract more than its fair share of amazingly talented entrepreneurs? Of course. Do they win competitive deals? Absolutely. Not always. But often. Have Marc and Ben attracted great partners? Sure. They now have a really wide group of talented investment partners like Jeff Jordan, Chris Dixon and others whom I respect.

So as far as I can tell, Rolfe’s article is a great summary of a snapshot in time for Andreessen Horowitz in which their returns look great and they likely have happy LPs but they are not yet the same return levels of the last few funds of Sequoia and Benchmark — two of the greatest investment firms in our industry. Most LPs would gladly invest in all three funds. Will those A16Z returns be significantly better in the future than today? We’ll see you in 5–10 years. Nobody knows.

But I do know that nobody I know in the industry (Ok, maybe 1 or 2 people) doubts that A16Z is building a great venture capital firm that will have enviable returns.

Photo credit: jdlasica via / CC BY-NC

(Cross-posted @ Both Sides of the Table)