Ep 305: Karen Page is a General Partner @ B Capital Group with a portfolio including the likes of Bird, Branch, Icertis, Evidation Health and Ninja Van to name a few. Prior to joining the world of venture, Karen was a Senior Director at Apple and before Apple, Karen spent an incredible 9 years at Box as a founding member of the executive team, where she was responsible for defining and leading Box’s Industry GTM strategy. Plus, from 2007 until 2013, Karen ran all of Box’s business development, partnership, and strategic alliance activities. If that was not enough, Karen is also on the board of some incredible companies including Deputy and Plastiq.

Pssst 🗣 Loving our podcast content? Listen to the start of the episode for a promo code to our upcoming events!

In Today’s Episode We Discuss:

* How Karen made her way into the world of SaaS as one of the first employees at Box and then how that led to her transition to the world of investing with B Capital.
* What were Karen’s biggest takeaways from seeing the hyper-scaling at Box? How did helping Aaron raise the Series B and onwards inform her view of what it takes to raise funding from the best SaaS investors? How does Karen think her mindset will shift when making the move from angel to now institutionally investing with B Capital?
* When does Karen think is the right time for startups to think about partnerships? What questions should they ask in the “dating” phase of a potential partnership? What are the red flags? Does Karen agree that signing a massive partner too early can be dangerous? What does Karen recommend in terms of getting in front of the best CIOs?
* Is Karen concerned by the compression of fundraising timelines? How does Karen meet entrepreneurs before they go out to raise? How does Karen advise founders when it comes to the question of whether they should always be raising or not?


Ep 306: Join Bessemer Venture Partners’ Alex Ferrara as he takes a look at trends and predictions for the cloud industry in 2019. One of the most popular sessions from SaaStr Annual, this presentation will provide an in-depth look at the cloud computing industry across Europe and globally.

This episode is sponsored by Owl Labs.


SaaStr’s Founder’s Favorites Series features one of SaaStr’s best of the best sessions that you might have missed.

This podcast is an excerpt from Alex’s session at SaaStr Europa 2019.


If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
Karen Page
Alex Ferrara

Below, we’ve shared the transcript of Harry’s interview with Karen.

Harry Stebbings: You are listening to the official SaaStr podcast with me, Harry Stebbings at H Stebbings 1996 with two Bs on Instagram and I would love to see you there. But to our show today, and I’ve wanted to have this guest on the show for a long time, being part of a rocket ship as early as this guest was, is such a unique experience and we had a blast unpacking that journey today, and so I’m thrilled to welcome Karen Page, General Partner at B Capital, with a portfolio including the likes of Bird, Branch, Fishbrain, Hollar, and MachineMax, to name a few. Prior to joining the world of venture, Karen was a senior director at Apple and before Apple, Karen spent an incredible nine years at Box, where she was responsible for defining and leading Box’s, industry GTM strategy. Plus from 2007 until 2013, Karen ran all of Box’s business development, partnership and strategic alliance activities.

Harry Stebbings: If that wasn’t enough, Karen’s also on the board of some incredible companies, including Deputy and Plastiq. I do also want to say huge thank you to the wonderful Aaron Levie at Box and Howard Morgan for the fantastic questions suggestions today. I really do so appreciate that.

Harry Stebbings: But that’s quite enough for me. So now I’m delighted to hand it over to our fantastic guest today, Karen Page general partner at B Capital.

Harry Stebbings: Karen, what can I say? I’ve wanted to do this one for a long time. I mean I heard so many good things, both from Aaron at Box and then also Howard Morgan. So thank you so much for joining me today, Karen.

Karen Page: I’m so happy to be here. Thanks for having me

Harry Stebbings: Not at all. But I do want to kick off with a little bit of you and your story into Venture, because it’s weird and it’s a wonderful world. But how did you make your way into the world of startups and how did that lead to today being a partner at B Capital?

Karen Page: I started my career in sales and marketing. I was living in Honolulu and I was working for LexisNexis and had the opportunity to move to Silicon Valley and I really had no idea what I was getting into. But when I moved here, I immediately was bitten by the bug that so many people get bitten by here, and knew that I was destined to be in the world of startups. And had the opportunity, my first startup experience was at Prosper. We had an incredible founder in Chris Larson, unbelievable market opportunity. I came on board as a VP responsible for building the community. We had Jim Briar on the board and Bob Kagel on the board. So I was really thrown into quite an incredible opportunity. But you know, I really feel like my journey started at Box.

Karen Page: Box is where I learned to lean into the unknown and to take a significant risk, and when I joined, the founding team, 50% of them were not yet 21. So it was quite a young organization. We had raised $1 million, that at the time was considered an A round, which we have seen that kind of evolve significantly since that time. And we really had no revenue to speak of by the time that I had joined. There was an incredible market opportunity and a lot of potential, no revenue and not a lot of money in the bank. I was a single mom with two young kids at home, financially responsible for my family and, honestly going to Box was one of the crazier things I’ve ever done.

Harry Stebbings: I absolutely love that in terms of kind of the risk taking mindset. Can I ask how did that then transition over the years into investing and now B Capital and VC?

Karen Page: I took a lot of time in understanding what the opportunity was at Box. I spent time with the original investor, Josh Stein from DFJ, and he’s the one that gave me kind of confidence to jump in. We immediately pivoted from a consumer company to a B2B company. And I was–also worked with Aaron quite closely on raising the B round of funding. Which was my first exposure to pitching and seeing how the venture community took on entrepreneurs and their thinking and the questions that they asked and the way in which the opportunities were evaluated and considered. And you can see when you’re talking to dozens of different VC firms at any given time, you can see how their mindset goes, what’s important to them. And often they were very different as we talked to various firms. Luckily we were able to connect with Mamoon Hamid at USVP at the time.

Karen Page: And we’re so lucky to be able to work with someone who was young in their career, but very committed to our growth. But that for me was an incredible opportunity to see how the venture community actually went to work. And again, thinking through how you get the bug of working for a startup. I knew in my mind at that point that I was going to be in the venture community at some point in my career. I think there’s a lot of serendipity that comes with intention. So my intention was to be in venture and serendipity led me there over the years.

Harry Stebbings: No, I totally agree with the serendipitous nature. I guess a really interesting question for me is now as an institutional investor, you had invested as an angel before and it’s a transition that I have been going through and I’m still going through now and it’s how did your investing mindset change with the shift from angel to institutional? And we had you know, Josh Koppelman and Andy McLaughlin and they both said that actually they became more conservative. How did your mindset shift in terms of that investment mindset?

Karen Page: I agree in theory with that because as you’re writing your angel checks, you know that they may very well go up in flames. And that’s the mindset that you come into it with, when you’re writing a check to a company at the seed stage, you know that the likelihood that that is going to fail is great. You still go into it with the hopeful expectation that it will be a success, but when you start thinking about it from the institutional perspective, you’ve got other folks that you are responsible to. You’ve got an LP base and you know that your future success is tied to their ability to extract success from the portfolio that you’re building. So certainly there is going to be some mindset around making sure that the companies that you’re investing in are going to be successful in the long run. So, that is a very big change.

Karen Page: But I think no matter the stage there’s going to be risks and the nature of the beast when it comes to investing is that your risk is going to evolve with the growth of the company. Early stage, there’s going to be demand risk and product market fit risk, but later the risk is about the ability to scale. And so when I think about it from an institutional perspective, investing at the growth stage, some of the risk has already been considered and hopefully worked through. Not all of it of course. The risks at the growth stage are going to be about, how can you scale? What is the ability of the company to continue to build an incredible team? Can the founder attract talent? What’s their passion level and how do they share that vision and then how are they going to scale with this new inflection of capital?

Harry Stebbings: Yeah, no, I totally agree with you in terms of there’s different risk profiles at different stages. When we chatted before though, you said something really interesting and I loved it. But you said, “Invest in people, not pitches.” And you definitely did that in terms of your time with 50% of the team at Box being below the age of 21. So how can I not dig in on this kind of people first approach? What did you mean by the, “Invest in people, not pitches?” And how does that maybe influence your investment decisions?

Karen Page: Yeah, the pitch is just one of it. Even if you’re in love with a business idea, you need to get under the hood with a founding team. How are they thinking about growing the company and the leadership team? How do they face tough challenges and navigate obstacles? Are they adding diverse talent that complements their own strengths and weaknesses? And founders cannot be all things to all people. They can’t be amazing at everything and that’s okay, but getting to know them as people, and how do they take guidance and support and how are they going to handle the challenges of navigating this growth. They’re all as important to us as the actual pitch might be. The pitch is important. It’s the presentation of an idea in a short amount of time and a chance to answer the important question. Does this idea have legs? Are we solving a critical real world problem? And do they understand the addressable market? But we really want to know the people. We know that innovation can come from anywhere. We want people who are going to be able to survive the challenges of growth.

Harry Stebbings: I’m so aligned to this kind of people first approach. My challenge today is funding timelines are so compressed given the excess capital supply, that you don’t have the time that you once had to really dig in in a lot of cases with rounds going three to 10 days, in many cases. How do you find the people first approach fitting in such a round compressed timeframe ecosystem?

Karen Page: You’ve hit the nail on the head. The time compression makes it super challenging. You can’t get to know someone in the way that you will over time in two days. Just doesn’t work that way. So ideally we’ve begun to work with the companies that we have spotted that matched the framework that we’ve outlined or the theses that we’ve set up. So we try to get to know people in advance of their funding rounds. Of course, that doesn’t always happen. So when we are faced with a compressed period of time and need to get to know the teams in a speedy way, we do have a framework, a people framework. So we start to pattern match against what we’ve seen be successful in the past, and we look through a criteria list that we have managed on our team to say just basic things.

Karen Page: How does this leadership team gel? How do they work together? What are we seeing is their strengths? How have we seen them communicate together? What can we learn from how they are approaching the challenges that they’re facing? What do we think will happen when there’s a conflict around direction of product? Or how the customer service team is going to deal with companies that aren’t renewing as planned? You know, we want to understand the thinking, the thought process of these teams. So while it’s not ideal to have to do this in a compressed way, we do think that we are formulaic in our approach and take the time required to understand the dynamics of the people.

Harry Stebbings: Really interesting. You said that about really getting to know them pre fundraising and that, totally with you there and that’s the ideal situation. For that to happen, founders have to be open to discussing and meeting investors when they’re not raising. We often hear today, only meet investors when you’re actually raising. Others, say you should always be raising. What advice you have for founders in terms of always raising, versus that kind of more disciplined head down on product and growth.

Karen Page: I, of course, as being on the venture side, like the idea of always be raising. It creates various opportunities and I think for us, we hope that founders are open to that perspective. We also think that we are a very young firm. We aren’t as well known as some of the others in our business. And for that, we like to take advantage of some of the surprising differentiators that we have with founders and often find that if we can meet them in advance, they actually are super interested in the BCG partnership and the ecosystem that we can build. And so it does give us a leg up if we can meet outside of the very compressed time of a dozen term sheets sitting on the table.

Harry Stebbings: Totally with you. In terms of that competitive landscape, we spoke about kind of your involvement in the Box fundraising and in many cases and Aaron mentioned it and your instrumental help. I guess if we switch also to the founder perspective, he asked us specifically, how much should founders think about early stage investors and what advice would you give founders when it comes to a crucial investor selection?

Karen Page: Absolutely. At each stage of growth. Look for the investors who know how to add the most value for where your company is going next. A lot of the success an investor can offer to an early stage company is their network. Who can we introduce you to? Who is going to be pivotal to you in your very early stages? And so that’s what is super important and critical at that very early stage. In fact, in my angel experience, many of the founders have wanted me to come aboard because of my experiences, my knowledge, my network, the people that I could introduce them to and the strategic advice that I’d be willing to offer them. As a company grows, it’s much more about what can be offered by that investor in terms of the strategy, the capabilities, and the individual and collective experiences of that investing team. And of course for us, one of those huge differentiators is the strategic capabilities of the BCG partnership that we bring to the table.

Harry Stebbings: Totally. I see that. When you look at your strategic experiences and insight, where do you find the ideal insertion point is for you? Is it in that pre product market fit phase? Is it in that scale up phase? How do you think about where maybe your strategic insight is most impactful?

Karen Page: So the growth round is the first time that founders receive a huge inflection of capital. And it requires an immediate shift in approach from testing and iterating and learning how to sell and build out processes and teams, to suddenly being expected to scale very rapidly and with a faster cadence, navigating pricing models, entering new markets.

Karen Page: And as a founder, that capital is the fuel to grow, but it doesn’t come with a formula. And what we see is that it’s just fraught with challenges. And we often experience the CEOs across the ecosystem facing the same types of problems. And we like to be there for them as they grow through them. And we can be an assistant to that growth. They’re not alone. It’s very interesting to me. You see CEOs who are navigating a problem and they feel like they are the only one, this is the only time that this has ever happened. And we can come in with a playbook. We can just, “Of course, we’ve seen other people who have hired a first time VP of sales that didn’t work out. And here’s what we think we can learn from this experience and we can move on quickly from it.” So we just like to compress the timeframe against the solutions to some of the problems that are very standard in the growth phases.

Harry Stebbings: We mentioned the intense scale up phase there. The big question that I often have for other investors is how do you know when to really pour fuel on the fire? And they say, “Ah, it’s when the unit economics all play out and we can really see the scale up story.” But then there’s a lot of other cases where it could be in traditional enterprise sales where actually sale cycles are just much longer. Where sales rep productivity’s maybe slightly more challenging to predict in the early days, or in marketplaces where actually you have to project your mindset out many years, three to five years to really see those unit economics. How do you think about when’s the right time to really pour fuel on the fire?

Karen Page: I think part of it is understanding the formulaic approach to go to market. If you haven’t yet determined what the markers are, what the sales cycles look like, and how to get through a sales cycle more quickly, then you might not be ready. That might be a good time to continue to AB test your go to market approaches. What’s working for you? Where are your customers coming from? But once you have a decent idea of where people are coming in, what markets are best suited to immediate attraction and immediate adoption, then you are ready to add fuel to that fire. Let’s find those markets where adoption looks pretty quick and also let’s learn to use the existing customers that have come in. How can we leverage their networks? We know that every CIO in the business is talking to every other CIO in the business. How can we begin to have people talk on our behalf? How can we begin to build networks where the products that you’re selling becomes part of the conversation?

Harry Stebbings: Totally agree with you, in terms of the product being central there. You mentioned the CIOs there. I often have the thinking that if it’s not a top one, two, or three buy for the CIO, it’s going to be a challenge to really get efficient sales cycles and see that kind of sales velocity within the funnel. Is that too short sighted of me now? Given the wide variety of vendors and software that CIOs have to really engage with? Or do you still maintain that actually, unless it’s a core, it is challenging to really get excited, especially from an investment perspective?

Karen Page: I think that we’re seeing a time, of course when CIOs and CSOs are up to their eyeballs with new technologies and just trying to keep up for their own companies to make sure that they are seeing the products and the services that are going to best solve their company’s problems. We know that that’s the case. They are overloaded today. However, I do think there’s room to have a conversation with them, when your product is in that bucket. It’s a transformational product that’s going to make a difference. You’re going to be able to get in front of CIOs that matter and that’s the key is figuring out what the entry point is, what the conversation looks like, and it may require creativity. It may require you camping out at a conference when that CIO speaking. But the ability to get in front, I think is also testament to the network and the community that you bring in from your investing team.

Harry Stebbings: I’m so sorry for going so off schedule, but I’m too intrigued. Once you do get in front of them, often people say about the importance of really selling the long term vision of kind of the product roadmap itself, and how that really plays into how they think about the partnership. How true is that versus actually the product today, what it can deliver for them on an ROI basis, on day of implementation? How do you balance between that immediate product, ROI versus vision, and is the vision really important, do you think in terms of really seeing that conversion?

Karen Page: So you want to paint the vision and share with them the compelling differentiators that your product offers. That goes without saying. It’s an art to be able to do that because they are inundated. However, there are other aspects to attracting the interest of the CIO, in terms of the community that they play in. One thing that we worked on very hard at Box was building a community of CIOs that gave you the right to access them. So we would bring them together, share important ideas, not only about Box, but about tangential software solutions that they were interested in, and we built a community around it.

Harry Stebbings: I love that in terms of the community building aspect. We see events being… And again, I’m sorry for the scheduling on again, but I’m too intrigued. You mentioned the community building and the events. Events is becoming more and more popular as a marketing strategy or as a community building strategy. How do you think about events today when you see it within your portfolio? Do you think that being underutilized, over-utilized? How do you think about it? Especially as a conversion tool?

Karen Page: It depends on the stage of the company and the type of event that they’re trying to hold. I really believe in the power of events, and I also know that they are far harder to execute successfully than you would imagine on the face of it. It takes a lot of strategic thought, and a lot of work to get the right ideas on the table to attract the right people to attend and then to put on an event that people are going to talk about after they leave, which is the key. And then I think you need to merchandise it. You need to not just stop at the event. You need to figure out what other angles can you push on. Do you need to follow that up with a Medium article? Do you need to have one event that’s focused on the deployment managers and then one that’s focused on the CIOs or CEOs? How do you bring it all together so it’s not just a one off event but rather a very well thought through way for the company to have a voice and to create a vision?

Harry Stebbings: I think a lot of people struggle with events in terms of the ROI and really tracing that back to revenue directly. It’s often the case in marketing and it’s a big question that I have, which is kind of marketing’s measurement of success. And I had a VP of marketing on the show the other day that said that you always have to tie the core number back to revenue, in terms of determining the success of marketing. Do you believe that’s the case? Or do you believe there are alternatives, be it brand impact, be it brand weighted market that actually can be equally weighed? How do you think about directly tying that measurement back to revenue?

Karen Page: So, I really strongly believe in the notion of credibility, awareness, and revenue as being the drivers of these strategic marketing/BD efforts. Sometimes you do an event and the only thing you want to do is leave your attendees with the idea that you are a credible solution, you’re a credible business. Other times it’s broad. You want to create awareness and at the end of the day, all of these things should feed back into revenue. Some efforts are entirely revenue driven. That is more rare. Generally the larger picture idea is how do we create credibility and awareness for our business that lead to revenue over time?

Harry Stebbings: Totally agree with you, especially as also being patient with that revenue over time. I often see people expecting ROI to be relatively immediate and I think people forget about the long term nature of ROI. I do want to touch on the element that we kind of touched on earlier, being kind of a CIO conversation and building partnerships for startups, because I spoke to Aaron a lot about this, actually, and he asked specifically, fundamentally what makes a great partnership for a startup and what are the core questions they should ask pre partnership?

Karen Page: Aspirationally at Box, we always targeted our dream partners and systematically and relentlessly worked to find an end. Responsively, we fielded requests to integrate and so on, but always we were looking for companies where we saw long term benefits, mutually beneficial outcomes, and committed and aggressive teams to execute on the deals. We all know the work starts after the ink hits the paper. So we wanted partners who rolled up their sleeves with us to go big, and we always said yes until we had to say no.

Harry Stebbings: Yeah, I love that tenacity and the hustle. I had someone on the show the other day, he said about the dangers of signing too big a partner too early in the company life. It’s often thought of as incredible and you know huge achievement when you sign one of those behemoth clients, but they were concerned about the dangers of it. How do you think about this? Do you think that’s a natural and right concern to have?

Karen Page: Yeah, I mean sometimes the idea of the deal gets lost in translation. I’ve frequently advocated to founders the dangers of overreach in this way. Getting a deal done is not too hard, but making a deal work is very, very hard. In most cases, you have to put your product and your philosophies in the hands of another team. You know you’re enabling them to sell your product and that’s tough and you’re expecting them to sell on your behalf. It’s time consuming. And requires tons of planning, a lot of training, traveling extensively, monitoring the deals and so much more. It really takes a lot of people to put that into action. So think very hard about what success post deal will require.

Harry Stebbings: In terms of that importance of post-deal and the integration element, and taking that with the element you said earlier about people centricity. I really struggle with the segmented SaaS companies that we see being built today, because you build a relationship with maybe a sales rep, and then you get passed off to someone else just as you make that commitment, and you have to build a new relationship with someone who you maybe don’t have that innate relationship and trust with. Do you see what I’m saying here? And do you think that’s a worthy concern into the questionable nature of kind of the segmented teams?

Karen Page: Yeah, well as it relates to a business development or a partnership team, I think there are hunters and there are farmers. And hunters never like to give up their deal. Even after the deal sign they want to stay involved. And the hunters are ready to dig in and they do all of the highly actionable, even sometimes transactional types of work. What are the list of 50 to a hundred things that we’re going to look at across every new partner that comes in? Do we want to be part of their sales kickoff? Are they doing annual events that we can integrate into? What should we co sponsor, what would, should we co write? What types of product marketing pieces do we need to generate and create? That is not what a hunter does and a farmer excels there. So internally, we know that that has to be the way that the deal moves forward.

Karen Page: From an external perspective. It’s how early and how soon and how systematically can we make sure that those teams–Because the same thing’s happening on the other side, they are going to have hunters and farmers as well and you have to make sure that those people get to know each other as quickly as possible, and we’re looking for synergies there. We’re looking for cohesiveness, and we’re also looking for the right person on the other side to lead the deal. Because it will not work if you’ve got a lower level managerial person who is going to operate off of a checklist and not be able to operate from a strategic perspective. So it’s a matching effort as well from company to company.

Harry Stebbings: Totally agree with that. You mentioned the element of speed there. In terms of timing, Aaron specifically, from Box asked, when should start ups as focus on BD in partnerships. And where do you see many going wrong? Having seen it firsthand at Box but also kind of pattern matching today as an investor?

Karen Page: There are so many ways that this can go off the rails. We believed at Box that it was an important, very early approach to have a partnership strategy. I was employee seven and that was my role, was to figure out how Box could navigate and use as leverage other companies. Many were large, some we built as an ecosystem model that were just like us going in and trying to build their business that we felt were tangential to the way that we were building our business. But it depends on the type of company that you have. And it’s also very dependent on the executive team commitment to building out a partnership strategy. If you don’t believe it’s important, then no one on in the team, no one in the company is going to be successful at navigating and building that, because you need everyone pulling on all cylinders.

Karen Page: You bring in a deal, it’s going to require engineering, product, sales, marketing. It’s going to require everyone to be committed to making it successful. So without that level of commitment, partnership strategies won’t work. But again, I think that the earlier that you bring in and you think through what your go to market approach is, what you’re going to need to be successful, will point to the need for a partnership strategy. So just understanding that and communicating that will point out, I believe and highlight to you when it’s time. Most of the time, it’s pretty early.

Harry Stebbings: Yeah, no, I do agree with you and I think you’re absolutely right. I think many people consider it too late. We’ve spoken a lot about your time with Box and Aaron. And do have to ask one final thing from Aaron, I’ve got to give him so much credit for basically constructing the schedule here. What a hero. He asked specifically and I love stories. So what’s your most memorable story from the early days of Box and working with Aaron? What sticks out to you?

Karen Page: What’s the story that I can tell?

Karen Page: I would say, honestly, I have so many amazing stories from my time with Aaron at Box. Hilarious stories, and we should certainly circle back to some of these. But from a pivotal aspect for me running business development, it was our first significant deal. The deal came about, surprisingly, due to a critical weakness in a new product Dell was coming out with. It was in 2008 and it was when the little mini computers were the rage. And they were about to launch theirs and realized that all of the competitors had a lot more storage on board those devices and theirs had two gigs and they were sort of freaking out. Because I had spent so much time and so much effort in my relentless effort to meet every senior business leader at Dell, from their various GMs and their innovation teams. They knew us and so it was pretty shocking.

Karen Page: I think we have maybe 15 employees at the time, but Dell came to us as they were looking to satisfy their competitive need. And we were able to hammer out a deal that was pretty transformational at the time. We became the cloud solution to extend the storage capacity on these mini devices. And I remember calling Aaron, I was at a conference, and telling him on the phone that we won the Dell deal and it was crazy. We were both in shock. We felt like it was just an incredibly huge opportunity for us to build momentum. And when that deal was announced, we had well over a hundred newspaper articles from the New York times to the Wall Street Journal and everywhere else in between. And it was an incredible credibility and awareness builder. And we had a ton of inbound SMB and enterprise action as a result. And so I feel like that was a pretty pivotal deal for us at the time. And it is one of the PG stories that I can tell.

Harry Stebbings: I absolutely love it. And yeah, that is one hell of a needle moving deal. So that’s awesome to hear. I do want to finish here, Karen, on my favorite, which is the quick fire round. So I say a short statement and then you give me your immediate thoughts. Are you ready to rock and roll?

Karen Page: Always ready to rock and roll.

Harry Stebbings: Okay, so favorite book and why?

Karen Page: Where The Crawdads Sing by Delia Owens. Because it’s an incredible example that it’s never too late for people to try something totally new. She was a 70 year old zoologist when the book was published and she worked on the book for a decade, and it came out to zero critical acclaim. But then the book broke every algorithm. It didn’t fit templates and it shocked the publisher. It was reprinted over 40 times. So it really defies history and precedent and it’s a breakout winner. And to me the story is a magical, fascinating, gut wrenching, and it’s filled with twists.

Harry Stebbings: Incredibly hard one to ask. Who’s the best board member you’ve sat on a board with, and what made them so special?

Karen Page: No, I love Dan Demmer at Open View. He is calm, cool, and collected with incredible enterprise experience. Always the voice of reason. He’s a really strong coach, he’s a leader and he also knows when to let the management team sort it out. So I think his approach is thorough but not suffocating and lets his founders lead.

Harry Stebbings: What’s the single toughest and best thing about your role with B Cap today?

Karen Page: I love so many things about B Capital, but what I love the most is we’re a startup. So I get to do all of the things from an internal team perspective that I love and externally I am able to really help drive our vision, our market presence, and really help to define who we are as we move forward with our second fund. And it has been an absolute joy and incredible experience for me.

Harry Stebbings: What do you know now that you wish you’d known when you wrote your first angel check? I love this one.

Karen Page: What I wish I knew then, was that this is a community. And just as in Silicon Valley, people are always willing to help each other. People in the investment community have been unbelievable and I wish I had known that it was okay to call a friend and say, what do you think about this space? What do you think about this business? I think it is an incredible testament to the strength of the Valley, that people here are willing to share ideas, discuss angles, discuss people, and there are so many people who are ready to sit down and talk with you anytime.

Harry Stebbings: I totally agree with you. Having done 3,000 interviews, and the thousand when pretty much no one had ever listened to the show. I totally agree with you there. Tell me the biggest inflection points in your life and how did it change your thinking?

Karen Page: This was a tough one for me. I feel like I have reinvented myself over the course of decades, many times. I honestly think it was meeting my husband. If you can imagine how transformational that is after having been single for a long time and finding someone who was an equal partner and someone who supported me in every single way possible. He has been an investment banker, a startup CFO, a startup CEO, and we’ve walked along the same path in many different ways. But having someone you can count on for solid advice, 24 seven has been an incredible strength to me and has given me a really solid foundation to launch into this new direction for my own career.

Harry Stebbings: Well, I’m eternally single so I’m hoping that inflection point is to come in my life. Fingers crossed.

Karen Page: Let’s talk about that. I’m sure my network can help you.

Harry Stebbings: I’m all ears after the show. Let’s finish on your most recent publicly announced investment and why did you say yes and get so excited?

Karen Page: Well, my most recent publicly announced investment hasn’t actually been yet publicly announced, but I’m going to talk about it anyway. It’s a D stage investment in FinTech based in San Francisco with an incredible market opportunity. Differentiated way for SMBs to finance their business in the short and long term and we are super, super excited. I absolutely adore the founder. I love the team and we think they are really poised for some significant growth in the next year. So stay tuned, that will be announced in the upcoming months, along with a few other deals that they wanted to put forward.

Harry Stebbings: I cannot wait to see the announcement, and as I say Karen, I’ve wanted to do this one for a long time, having heard so many good things, but thank you so much for joining me today and I’ve absolutely loved it.

Karen Page: I have loved it too. Thank you so much.

Harry Stebbings: My word. I just loved having Karen on the show there, and such exciting times ahead for her with B Capital. And if you’d like to see more from us, you can on Instagram at H Stebbings 1996 with two Bs. It’d be great to see you there. 

Harry Stebbings: As always, I so appreciate all your support and I can’t wait to bring you a fantastic episode next week.



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