Welcome to Episode 189! Craig Walker is the Founder & CEO @ Dialpad, the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris’s Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product managed Google Voice. Before that Craig founded Grand Central Communications, a personal communications startup that was acquired by Google. Finally prior to that, Craig enjoyed roles in the world of VC as General Partner @ Sterling Payot Capital and Founder & Senior Director of Yahoo Voice.

In Today’s Episode You Will Learn:

* How Craig made his way into the world of SaaS following time as both a GP in the world of venture and then as the creator of what would become Google Voice.

* Why does Craig think go-to-market is the most challenging element of being a CEO? How does Craig think about when is the right time to go large on go-to-market? Where does Craig believe most founders make mistakes here?

* How does Craig look to balance aggressive scaling of team with the maintaining of early company culture? What are the foundations to doing this successfully? How does Craig approach the element of hiring external talent vs promotion from within? How does Craig think about managing the internal discontent if hiring an external candidate?

* How does Craig assess the effectiveness of trials in attracting large enterprises? What are the parameters that must be set for a trial, before it is agreed? What must founders learn to say no to when it comes to trials? How does Craig approach discounting? Why does Craig argue if your client asks for aggressive discounts, you have not explained your core USPs successfully?

Craig’s 60 Second SaaStr

* What does Craig knows now that he wishes he had known at the beginning?

* When I say success in SaaS, who does Craig first think to and why?

* Quality or quantity of logos and why?

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Jason Lemkin
Harry Stebbings
Craig Walker


Harry Stebbings: Welcome back to the official SaaStr podcast with me, Harry Stebbings. Now, I’d love to have you more involved in the making of the show. So, on Instagram at @hstebbings1996 with two B’s, you can both suggest questions for future episodes and put forward potential guests. It’d be great to see you there. However, to our episode today and the founder that I’ve wanted to have on the show for a long, long time. And so, I’m thrilled to welcome Craig Walker. Founder and CEO at Dialpad, the startup that provides a business phone system for the modern workplace. And to date, Craig has raised over $120M in VC funding with Dialpad, from some of the very best in the business, including Iconiq, Andreesen Horowitz, Google Ventures, Felicis, and Bill Marris’ Section 32. Prior to Dialpad, Craig was an EiR at Google Ventures and founded and product managed Google Voice. Before that, Craig founded Grand Central Communications, a personal communication startup that was acquired by Google. Finally, pre Grand Central, Craig enjoyed roles in the world of VC as general partner at Sterling Payot Capital. And founder and senior director of Yahoo Voice.

I do also have to say a big thank you to John Kim at Amasia for the intro to Craig today. I really do so appreciate that.

But that’s quite enough of this dulcet English accent, so I’m now thrilled to hand over to Craig Walker, founder and CEO at Dialpad.

Craig, it’s absolutely fantastic to have you on the show today. A big hand to Jonathan at Workbench for the intro, but thank you so much for joining me today.

Craig Walker: Yeah, thanks for having me. Thrilled to be here.

Harry Stebbings: Not at all. I wanna kick off this thing with a little about you and how did you make the way from creating Grand Central and ultimately what became Google Voice to moving to the world of SaaS with the founding of Dialpad and what was that founding story?

Craig Walker: So, I had left a job at Yahoo, where they had acquired a prior startup called Dialpad, funnily enough. And we had started–Vincent Paquet, who ran product for me–he and I started a company called Grand Central, it was all about controlling your communications, and at the time, this was 2005. People had a cellphone, they had a work phone, they had a home phone, they had voicemail in every different spot and it was really annoying. So we gave you a number that rang you everywhere and moved all your features to the Cloud and that became Google Voice once Google came and acquired us in 2007.

So we did that for 3 years at Google and realized that businesses were moving to the Cloud for their email, for their CRM, for their documents and we realized that voice was going to be the next big thing to go to the Cloud for businesses. So, we left in 2010, we got fronted by Google Ventures. I was actually an Entrepreneur in Residence at Google Ventures for a little while. We really built a Cloud-based enterprise voice product and then we went back to our friends at Yahoo and got them to sell us back the name Dialpad that they acquired in 2005. So, it kind of comes all full-circle, we got the name back from Yahoo. And that really built on the concept of how people work in the modern world and a lot of it is fully mobile and being able to do anything from anywhere and make it seem like you’re still at work. So, being able to have all your business communications just in the palm of your hand or in your pocket with your cellphone.

Harry Stebbings: Can I ask, you mentioned your time at Google there, I’m super intrigued. What were the biggest takeaways for you from that time that were maybe kind of transferrable to you and the starting and scaling of Dialpad.

Craig Walker: Yeah, I’d say one of the best things about Google was that it was very entrepreneurial and it was about a fifth of the size of how it is today but it was a big crazy startup inside there. So, we were able to experiment and really have a lot of flexibility with the product but the one thing that was really, really important was – in order to launch a product or a consumer product at Google, it had to be able to scale to millions and millions and theoretically hundreds of millions of users so it had to be built and architected in a way that would allow that kind of scale.

So, the way we rebuilt Grand Central to make it Google Voice was in a Cloud-based architecture, that really allowed for that kind of scale at high quality so when we left to go start this company, we already had that training and that experience and we basically built a modern version of that Cloud architecture here. We have paying customers in over 50 countries and we turn them on or add seats without even thinking about it and it’s because we were built in that same scalable way. I think the willingness to experiment and the requirement to build for scale were two of the best things that came out of Google.

Harry Stebbings: I love that building for scale learning, but I do want to break the [inaudible 00:05:03] up into a couple of different segments. I wanna start on some foundational technical aspects of go to market strategies, then move just to less tangible learnings on culture and finish on some good old advice on when to say ‘No,’ sound good?

Craig Walker: Yeah, that sounds great

Harry Stebbings: So, starting on the go to market advice, I wanna withhold assumptions and my opinions and put the ball in your court here, Craig. So, when’s the right time to go large on go to market?

Craig Walker: It’s a great question because when you’re launching a product, kind of like the natural SaaS progression is you build a online SMB type product first, you slowly add features, you slowly add bigger and bigger customers and ultimately down the road, you then start hiring expensive enterprise sales folks to go after big enterprises. We had a really different experience. One of our very first customers was Motorola Solutions, so we won a 20,000 person company as a customer, straight out of the gate. So, it forced us to accelerate our go to market and it’s really a challenge for any startup of when you put in all those resources to go after the big enterprise. Because it’s expensive. You hire a enterprise field sales rep, not only do you pay for that rep, who’s generally pretty expensive, but then they also need support of a sales engineer and they also need support of a solutions architect, and they generally have a piece of a vice president who sits over them.

It ends up, when you go to market at the big enterprise head, it’s almost like an aircraft carrier battle grip where you have the aircraft carrier but it’s got destroyers and frigates and submarines and all these other things around it. That’s how you kind of feel about enterprise go to market, so it’s really trying to find the right time when you really do see that there’s that product market fiit that enterprises are buying it and are happy and your company can support them and you’re not just getting pecked to death by ducks. This is kind of getting to your third one, of when to say ‘No,’ but enterprises will ask you for real custom solutions or they have some special way of doing things that they want you to tweak your system for and so it’s really tempting to say, “We want to go after enterprise because they pay they most and there’re super big budgets,” and things like that but it does come at a lot of cost and a lot of investment so you gotta make sure you’re ready for it. It’s a long answer of saying, you should know when the market starts asking for it. Once you do have that product market fit, really going after it hard is important because getting a great enterprise customer just pays ridiculously good dividends because generally, they’re large and they expand and they pay on time and they’re really good customers to have.

Harry Stebbings: You mentioned the advice there about custom technology, what advice would you have on customizations and some learnings on that?

Craig Walker: Ooh, it’s tough. Particularly as a startup, because your sales guys will go out there and they wanna get a sale. More than anything, they wanna get involved in deals and they wanna win. Often times, they’ll want to do unnatural things too–not unnatural but sometimes there’s requirements that you just don’t have at the time. They’ll say, “Look, if we win this deal, can we get it built in 30 days?” And it is so tempting to say ‘Yes’ to that every time because everyone’s competitive and everyone wants to win those deals and you have a great engineering team that you feel you can give more to.

But at the end of the day, the way we look at it is, we’ll take on additional features or additional pieces that we don’t have but we’ll only do it if we think it’s gonna be for more than just that customer. Right? We won’t do a custom thing for one particular customer. It’s just too hard to manage and maintain. But if we think that it’s something that would help a lot of different customers, it’s probably already on our road map and then we’ll likely move it up the road map in priority to win a deal. But it is – you’ll get a big company saying, “Hey, we built this custom ERP system that we’d like you to integrate with and if you just do that, you win this deal.” You can go down a rabbit hole pretty quick building a lot of custom stuff and there’s generally no guarantee that that will even get you the deal. So it’s something that you gotta keep an eye on and make sure you’re not stressing your engineers too much on.

Harry Stebbings: Absolutely. In terms of the go to market though, we’ve discussed it before and you mentioned that building sales capacity. What have been some of your biggest learnings on building sales capacity successfully with Dialpad and really in sync?

Craig Walker: What we found, I think this is a unique time in the world to be able to do this but we try to build all of our products that are really simple for the end user and delightful for the end user. So at the end of the day, even though we’re selling to a large enterprise, we still want it to be simple enough that a small business could come online and go buy it. We have the benefit of having a big self-serve online piece of our business that grows and maintains itself that doesn’t require a big sales investment. Then, we hired a team of inside sales reps. We have three teams for our inside sales, one for the West Coast – and this is all US focused right now, but one for the West Coast, one for the Central and one for the East and those generally work out of our San Francisco and our Austin, Texas, office and they’re handling phone calls and emails and really selling probably up to about 750-person sized companies.

Then, for the go to market on the enterprise, the big 750 to 20,000 type employee companies, they’re out in the field. They’re in New York, they’re in Chicago. They’re in San Francisco, they’re in Los Angeles. They’re in all the places where you think all those companies are gonna be and they’re out spending nine months to close a single deal but if they close that single deal, it’s potentially a multi-million dollar deal and it’s well worth the investment. So, it’s really kind of three-pronged, online, inside and outside.

Harry Stebbings: You mentioned inside there, we have a lot of founders coming to me, struggling to scale their inside and really make it an effective machine. What have been some big learnings for you in really building and getting that really effective machine of inside sales?

Craig Walker: It’s a really tricky thing to get right but once you get it right, it’s good. So, first is, you gotta have the right product and you have to have the focus on the right buyers. We look at companies in basically three categories.

One is a company that’s born in the Cloud, they’re probably less than 10 years old but they always started in the Cloud, they don’t have a lot of legacy stuff to switch off of. And we do really well with those type of companies and those are customers like WeWork, Uber or Domo or Stripe. Those type of companies just make a ton of sense for us.

Secondly, there’s companies that are older but moving to the Cloud like Motorola or Gate Gourmet or Remax or Keller Williams so things like that.

The third set of companies are the ones that are not in the Cloud, are not interested in the Cloud, don’t have a CIO that sees the benefit of it and those we try to avoid.

So, in order to be effective in our inside sales and even outside sales is step one is really targeting on the right type of buyer and the one where our message is going to make a lot of sense. And then giving them the right training and the right enablement and the right pitch stacks and then just having the proper cadence and activity and follow-up and coaching. It’s just a never ending cycle of staying on top of that but if you have the right target, you have the right enablement, the right pitch and the right activity, generally it’ll work out pretty well. We’ve seen really good uptake in the commercial segment just because it takes a while to get there but it’s all starting to really hit now.

Harry Stebbings: For sure. In terms of it hitting and that feedback and reporting, VCs often kind of aggressively push on the go to market. Jason Lemkin always tells me that founders should posit and suggest targets that they have a 30% chance of hitting, how would you respond to this? How do you approach the reporting and feedback element?

Craig Walker: Yeah, it’s interesting because investors love, if you look at all the SaaS companies that have gone public and have had these great breakout multiples, most of them have had a pretty good large enterprise story and they’ve started small in SMB but they’ve made the move to enterprise. Investors love to, want to see you go be a big enterprise company. It is a matter of timing and it is a matter of when you have the right product market fit, when you have that right target buyer, when you have that right enablement and everything else.

I’ve seen companies where they’re burning $10M dollars a month just to fund 75 field sales reps. They may go and build a good pipeline but at the end of the day, it’s an unsustainable model. So it really is to me, you gotta find out when’s the right time to double down and invest. We just closed a $50M Series D round and we think we’re at that point now and we think we have the right product market fit, we’ve identified the right buyers. Now for us, we’re going heavily at it but we’ve been at it for seven year,s so it does take some time to get to that right time when the dials all line up, when you think it makes sense. It’s for an investor or a founder out there, being able to know when that time is is important because you can run through all your capital pretty quickly if you do it too quick.

Harry Stebbings: Speaking of knowing when that time is and really moving heavily into the scale element, I’m really interested in the kind of transition from that startup to more of the professionalization and turning into a real company. How do you think about that? Without losing the very startup fabric and culture that got one company to where it is?

Craig Walker: That’s a great, great question just because it is a challenge. We’re at 300 employees now and we’re gonna be at 400 by this time next year. That’s a lot different from when it was the first 10, 20, 30, 40, 50 folks and in those early days most of you would work to get, in our case, almost all of us had worked together either at Google Voice or even going further back to Yahoo, even further back beyond Grand Central, so you go from this really intimate setting where everyone understands each other because you’ve worked together so closely and all of the sudden, you’re at this real company with hundreds of people and all the sudden you have to do grown-up things.

So what we did is we hired a great head of HR, Tasha Liniger from BlueJeans, she came in and put in a whole bunch of structure and proper management training, proper development, proper compensation, pants, proper feedback and just kind of built the machinery that allows the company to grow without frustrating everyone but still  being true to yourself and keeping that culture alive is something that we work on all the time. We do, every Friday, all hands meetings where anyone in the company can ask me any question, I’ll do my best to answer it. We give business updates and I fly to all our offices and just do everything I can to make it still seem like a small company while it does scale because at the end of the day, you can look up and seven years have gone by, it’s a real business and you have to do the right things to help your employees  in progressing their careers and get feedback they need and get promoted and get raises and all those types of things. Sometimes, in the startup world, you’re so heads down you don’t even think about that stuff. So it does require some real conscious effort to do it.

Harry Stebbings: In terms of that scaling and the team, you mentioned that, the additional 100 people you’ll have in a year. The core elements being obviously attracting that best talent and then retaining it. Starting on attracting, what have been your takeaways in scaling Dialpad in terms of truly attracting those A star players?

Craig Walker: I think a couple of things. One is, the people we try to attract are the ones that want to get their hands dirty, that want to make something, that really want to own an interesting project and we do really well when we recruit against, pull people out of a big company like say, versus Cisco or Microsoft just to name a big company by example, a lot of times they’re able to recruit and hire these really, really talented developers but then they work on a tiny, tiny little bit of  a very overstaffed project. If you’re working on one little part of one feature of one product on Microsoft Office, just to pick on Microsoft. For a lot of folks that isn’t all that thrilling. So, we give them a ton of responsibility and say “Look, you’re going to be responsible for multi party video and there’s going to be three of you working on this and you can experiment different ways to do it, you’re limited only by your own imagination. So I think that having interesting products to work on in a growing space at a growing company that feels like the opportunity is now, that really helps on the attracting. Just having a culture where people are honest and open and fair and hopefully that comes through during the interview process and they get feedback from their friends who work here who’ve gone through the interview process and it all just kind of perpetuates.

We have a culture, we have a phrase of “Do the right thing.” We apply that to everything, including our recruiting.

Harry Stebbings: If one is recruiting and is recruiting an external candidate for a position, how does one prevent internal discontent when there’s maybe an existing team member or two that would like the promotion, how do you prevent that discontent when the external hire gets the job and how do you think about that?

Craig Walker: We try to promote from within as much as humanly possible. We’ve done a pretty good job at that. Generally, if you have to go bring in a real senior executive, it’s because it’s just a gap on your team. When we hired a Chief Marketing Officer, we didn’t have – this was years ago but it was clear that we needed a Chief Marketing Officer and the folks who were on the team were doing good spot pieces but no one was ready for that role. But generally, we’ll try to promote from within and not have to bring in outside senior people. It’s actually relatively rare when you do do that. Mostly at kind of the C level, you need a CFO, you need a head of HR, you need a CRO, you need a CMO. Those generally are the types of ones that come in but for developers and designers and product managers and sales reps, those we all try to cultivate and really grow from inside.

I’ll tell you this too, that they all love when new people come join the team because there’s more than enough for everyone to do and we want to move faster and do more stuff so everyone’s generally thrilled when the teams grow.

Harry Stebbings: Now, I do want to finish today, and before we move into the quickfire, on an element which I need your help on here, Craig and it’s learning to say ‘No.’ In the heat of scaling customers, scaling teams, it’s easy to say ‘Yes’ to everything just to feel the growth but we’ve discussed before, the importance of saying ‘No.’ So, starting broadly, what’s your overarching thesis on when to say ‘No?’

Craig Walker: Yeah, I think you have to be really disciplined on what it is you do really well and what it is, what’s your competitive advantage and not trying to be everything to everyone because there’s too many shiny objects out there and your sales guys will come back with deals that all you have to do is just create some custom thing and then you’ll theoretically win that deal or there’ll be a business development conversation with another company that, “Hey they’d love to integrate, if you could only do this certain, particular, weird way for them.”

And at the end of the day, I’ve seen plenty of times, there’re deals where you end up taking the bait like ,”Okay, let’s do it, this sounds exciting.” And then you spend three to six months working on it and then at the end of the day, nothing comes of it. And then you’re super frustrated because you’ve now wasted time, changed your road map and it really didn’t pan out. So what I try to do is say, “Look, we know what we are. We’re great at business communications and we’re really, really good at voice and video and messaging and so all of our products are gonna be focused around that.” And if someone comes to us and says, “Hey, it would be awesome if you could build a to-do list to go with my meetings or some archiving of something else or can you integrate with these 40 different legacy systems?” Yeah, the answer’s no. We could, but we’re not going to.

And the reason we’re not going to is those developers are going to be, I’d rather have them working on the things that I think are going to be more important like Artificial Intelligence, that’s something I’m really excited about. We’re putting Artificial Intelligence into all of our calls and I would love my developers to spend their time on that rather than having to work on some legacy phone system feature that nobody’s going to use. So it really is just trying to be true to yourself and figuring out where you have a differentiated advantage and really double down on that.

Harry Stebbings: In terms of kind of founding questions on when to say ‘No,’ it often kind of arises in two elements, discounting and pilots. In terms of discounting, how do you think about this more broadly with the scaling of Dialpad, have there been some learnings for you on when to say ‘No’ in discounting conversations?

Craig Walker: Yeah, it’s interesting because everyone’s competitive, you don’t wanna lose deals and then the people you’re fighting against are theoretically, will be in there offering really, really lower prices to try and win a deal, and I think it comes down to really having confidence in your product, that it’s a differentiated solution, it provides much better value and if someone’s looking at it and looking at it, comparing it to a competitor, and thinks it’s just a matter of, “Hey, this guy went down to X and you’re up at Y.” Then we didn’t do a good enough job explaining the differences and that’s on us, but at the end of the day, I don’t wanna get into to a discount war. I think we’ve got a uniquely great product and it’s going to make everyone more productive and it’s worth a couple dollars more. So, we try to avoid it, but let me tell you, when you’re a startup and you wanna win deals and a big deal’s right in front of you, they want a lower price, it is hard to say ‘No,’ but now that we’re mature enough and big enough and I think that we have the right product market fit we’re to a point we can say ‘No’ to that pretty easily.

Harry Stebbings: I think you’re absolutely right, in terms of being at that scale to say ‘No.’ In terms of the other element, being the pilot element, how do you assess pilots today, is that kind of customer acquisition bridge and what elements would force that bridge into a ‘No’ for you?

Craig Walker: Sometimes people want, it almost feels like an endless pilot. “I wanna test it for three months.” That’s just too much, and we’ll do pilots, we do proof of concepts, we do a lot of, we let people use the product is a lot. In fact, we actually have free versions of our product. If they wanna get comfortable with it, they can go use our free versions of the product and get as comfortable as they want. But by the time it takes to go deploy a large company, to really train them and do the change management, and really make it a smooth onboarding, you gotta be able to do that efficiently and neverending pilots or long pilots just sap all your energy and make it impossible to be efficient at that. I generally like to say “Look, come use our stuff. If you wanna full-blown pilot, we’ll do that but it’s going to be limited in duration,” and we can get you comfortable, we have reference customers, we have analysts, we have all these things you can do to learn about us but saying ‘No’ to the endless pilot is something you gotta learn how to do otherwise you’re just always going to be juggling endless pilots.

Harry Stebbings: The endless pilot is never a winner, but I do want to move into my favorite of any interview, being the quickfire round. So I say a short statement, Craig, and you give me your immediate thoughts. Does that sound good?

Craig Walker: Yeah, I love it.

Harry Stebbings: So tell me, the quality or quantity of logos in the early days, what’s important?

Craig Walker: The quality. So you’ll want ones that’ll be referenceable, you want to have ones that people will recognize and I’ve seen competitors, I’ve seen other people’s logos and they just put up every logo. Like one guy in this million person company uses our product and they put up that logo, it loses some credibility when it’s not real. So I’d say real, referenceable, quality logos is the most important thing.

Harry Stebbings: What’s the most challenging role to hire for and why?

Craig Walker: Mobile developers and they are just in such demand by every company, and it’s really hard to find good ones with a lot of experience, and they’re really hard to get.

Harry Stebbings: Tell me the hardest element to learn is a SaaS founder scaling.

Craig Walker: Geez, the hardest element is the go to market. The go to market is really the hardest element. To me, it’s not the product and it’s not the platform and it’s not design or support or any of that stuff, it’s when and how you fund that go to market and who’s the right person to lead it and when do you go all in? When do you probe? It’s really kind of an interesting exercise.

Harry Stebbings: Totally off-track, but I have to ask with that in mind, when do you really shift your thinking into prioritizing unit economics and that kind of granular level sustainable financing?

Craig Walker: It’s got to be part of it from the start. We’ve always tried to be really efficient, I remember I was a startup guy in 2001 when the world ended so I’ve seen good days turn into dark days pretty quickly so I’ve always kind of had unit economics on my brain and when you’re going in pitching VCs and talking to them, you do have to show them your margins and you do have to show them your churn and you do have to show them your customer acquisition cost and all those things. So, thinking about that early and making sure you have a sustainable business model is, I think, seems like something you should all be doing from day one.

Harry Stebbings: When I say success in SaaS, Craig, who’s the embodiment of this to you?

Craig Walker: Great question. I think companies like Zendesk, companies like Salesforce, ServiceNow, companies that have just owned a category and run away with it and continue to. Atlassian’s been fantastic, Bessemer Venture Partners has–their cloud index, it’s up a ridiculous amount over NASDAQ and the Dow. A lot of those companies are in there, like Shopify, Square, just Cloud-based companies that are crushing it. But I’d say Zendesk is almost the perfect match. They serve everyone from SMB, to mid market to enterprise. They’ve added a lot of functionality over the years and they’ve just continued to run away with the support market.

Harry Stebbings: Now, my favorite and final question. What do you know now that you wish you’d know at the beginning? Now, you can choose the beginning time. It can be the beginning of Dialpad V2 after Google, it could be the beginning of Dialpad V1, but what do you know now that you wish you’d known at the beginning, dot dot dot.

Craig Walker: I would say, I wish I had hired a HR business partner, a head of HR earlier, we’ve just added one in our sixth year of the company and I think I would have done much better on other hires had I had that in place and when you’re just battling day to day and scaling and hiring and going to market and stuff, it’s hard to take a step back and really have a strategy around it. Had I done this, If I were to do it again, I’d bring that person in much earlier ’cause I think that helps you scale, it helps you recruit, it helps you grow without a lot of these growing pains that you go through when all of the sudden, you have 300 people and it’s like, “Wow this is a real company, we gotta go put a lot more support into it.” So that would be the one thing I’d change.

Harry Stebbings: Craig, as I said, I heard so many great things from the team of GV, to Jonathan at Workbench, so thank you so much for joining me today and I so appreciate it.

Craig Walker: Yeah, I loved it. Look forward to talking again in the future.

Harry Stebbings: What a special episode that was, to have Craig on the show. And you must check him out on Twitter at @cwalker123 and we’d love to see you behind the scenes at SaaStr and you can follow us on Instagram where you can suggest both questions and guess for future episodes. You can do that at @hstebbings1996 with two B’s. As always, I so appreciate all your support and I cannot wait to return to the dark side of the table next week with our interview with enterprise investor Ed Sim at Boldstart.



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