A New VC Ready to Go!

One of the interesting things about being in business for 13 years (as of last week!) at Return Path is that we have been around longer than two of our Venture Capital funds.  Fortunately for us, Fred led an investment in the company with his new fund, Union Square Ventures, even though his initial investment was via his first fund, Flatiron Partners.  And even though Brad hasn’t invested out of his new fund, Foundry Group, he remains a really active member of our group as a Board Advisory through his Mobius Venture Capital investment.

Although our third and largest VC shareholder, Sutter Hill Ventures, is very much still in business, our Board member Greg Sands just announced today that he has left Sutter and started his own firm, Costanoa Venture Capital, sponsored in part by Sutter.  The firm was able to buy portions of some of Greg’s portfolio companies from Sutter as part of its founding capital commitment, so Return Path is now part of both funds, and Greg, like Fred, will continue to serve as a director for us and manage both firms’ stakes in Return Path.

The descriptions of the firm in Greg’s first blog post are great – and they point to companies like Return Path being in his sweet spot:  cloud-based services solving real world problems for businesses, Applied Big Data, consumer interfaces and distribution strategies for Enterprise companies.

I give Greg a lot of credit for going out on his own with a strong vision, something that’s unusual in the VC world.  We’re proud to be part of his new portfolio, and I’m sure he’ll be incredibly successful.  Like Fred and Brad and their new firms, Greg understands the value of being able to write smaller initial checks and back them up over time, he is a disciplined investor, and he is a fantastic Board member and mentor.

Not Just About Us

When we updated our values this year, we felt there were a couple critical business elements missing from this otherwise “how” series of statements.  One thing missing was our clients and users!  So we added this value to our list:

Not Just About Us:  We know we’re successful when our clients are successful and our users are happy.

This may be one of the most straightforward statements of all our values, so this will be a short post.  We serve lots of constituencies at Return Path.  And we always talk about how we’re a “People First” organization and what that means.  I suppose that inherently means we are a “Client Second” organization, though I’m not sure we’d ever come out and say that.  We do believe that by being People First, we will ultimately do the best job for our customers. 

 That said, we aren’t in business just to build a great company or to have an impact on our community.  Or even our shareholders.  We are also in it for our customers.  Whether we are producing a product for mailers, for ESPs, for ISPs, for security companies, for agencies, or for end users, we can’t forget that as an important element of our success every day.

I just said this to a fellow little league coach, and it’s certainly true for baseball.  I’ve coached games with sloppy and/or blowout wins in the past.  You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game.  And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run.  You are sad about the L, but at least you left it all out on the field.

Is that statement true in business?

What’s an example of a “bad” win?  Let’s say you close a piece of business with a new client…but you did it by telling the client some things that aren’t true about your competition.  Your win might not be sustainable, and you’ve put your reputation at risk.  Or what about a case where you release a new feature, but you know you’ve taken some shortcuts to launch it on time that will cause downstream support problems?  Or you negotiate the highest possible valuation from a new lead investor, only to discover that new lead investor, now on your Board, expects you to triple it in four years and is way out of alignment with the rest of your cap table.

On the other side, what’s an example of a “good” loss?  We’ve lost accounts before where the loss was painful, but it taught us something absolutely critical that we needed to fix about our product or service model.  Or same goes for getting a “pass” from a desirable investor in a financing round but at least understanding why and getting a key to fixing something problematic about your business model or management team.

What it comes down to is that both examples – little league and business – have humans at the center.  And while most humans do value winning and success, they are also intrinsically motivated by other things like happiness, growth, and truth.  So yes, even in business, sometimes a good loss is better than a bad win.

A while back, we were having some specific challenges at Return Path that were *really* hard to diagnose.  It was like peeling the proverbial onion.  Every time we thought we had the answer to what was going on, we realized all we had was another symptom, not a root cause.  We’re a pretty analytical bunch, so we kept looking for more and more data to give us answers.  And we kept coming up with, well, not all that much, besides a lot of hand-wringing.

It wasn’t until I went into a bit of a cave (e.g., took half a day’s quiet time to myself) and started writing things down for myself that I started to get some clarity around the problem and potential solutions.  I literally opened up a blank Word document and started writing, and writing, and writing.  At first, the thoughts were random.  Then they started taking on some organization.  Eventually, I moved from descriptions of the problem to patterns, to reasons, to thoughts about solutions. 

But what really put me on a track to solutions (as opposed to just understanding the problem better) was starting to *talk* through the problems and potential solutions.  It didn’t take more than a couple conversations with trusted colleagues/advisors before I realized how dumb half of my thoughts were, both about the problems and the solutions, which helped narrow down and consolidate my options considerably.

Even better than solving the problems, or at least a driver of being able to solve them, is feeling more in control of a tough situation.  That’s probably the best thing I’ve learned over the years about the value of articulating problems and solutions.  For a leader, there is no worse feeling than being out of control…and no better feeling than the opposite.  Some level of control or confidence is required to get through tough times.

I suppose this post is not all that different from any 12-step program.  First, admit you have a problem.  Then you can go on to solve it.  But the point I am trying to make is more than that – it’s not just admitting you have a problem.  It’s actually diving in deep to the potential causes of the problem, and writing them down and (better) speaking them out loud a few times, that puts you on the road to solving those problems.

The Best Place to Work, Part 6: Let People Be People

Last week, in this continuing series on creating the best place to work, I talked about being a great enabler of people, meaning you do your best to let people do their best work.  This week, I want to talk about Letting People Be People.

I wrote about topic a bit this last year when I wrote my series on Return Path’s Core Values, in particular the post on our value People Work to Live, Not Live to Work .

Work-life balance is critical.  I’ve worked in a grind-it-out 100-hour/week environment as an analyst before.  Quite frankly, it sucks.  One week I actually filled in 121 on my hourly time sheet as a consultant.  If you’ve never calculated the denominator, it’s only 168.  Even being well paid as a first-year analyst out of college, the hourly rate sucked.  Thinking about 121 gives me the shivers today…and it certainly puts into perspective that whether you work 40, 45, 50, 55, or 60 hours in a given week can pale by comparison, and all still let you have a life.  An average week of 40 hours probably doesn’t make sense for a high-growth company of relatively well-paid knowledge workers.  But at 121 you barely get to shower and sleep.

While you may get a lot done working like a dog, you don’t get a lot more done hour for hour relative to productive people do in a 50-week environment.  Certainly not 2x.  People who say they thrive on that kind of pressure are simply lying – or to be fair, they’re not lying, but they are pretending they wouldn’t prefer a different environment, which is likely disingenuous and a result of rationalizing their time spent at work.  Your productivity simply diminishes after some number of hours.  So as a CEO, even a hard-charging one, I think it’s better to focus on creating a productive environment than an environment of sustained long hours.

Work has ebbs and flows just like life has ebbs and flows.  As long as the work generally gets done well and when you need it, you have to assume that sometimes, people will work long hours in bursts and sometimes, people will work fewer hours.  Work-life balance is not measured in days or even weeks, but over the long term.  So to that end, We Let People Be People as a means of trading off freedom and flexibility for high levels of performance and accountability.  At Return Path, we create an environment where people can be people by:

• Giving generous maternity leave and even paternity leave, at least relative to norms in the US
• Having a flexible “work from home” policy, as people do have personal things to do during the business day from time to time
• Allowing even more flexible work conditions for anyone (especially new parents) – 3 or 4 days/week if we can make it work
• Letting people take a 6-week paid sabbatical after 7 years, then after every 5 years after that
• Having an “open vacation” policy where people can take as much vacation as they want, as long as they get their jobs done

As with all the posts in this series, this is meant to be general, not specific.  But these are a few of the things we’ve done to Let People Be People, which has created an incredibly productive environment here where people have fun, lead their lives, and still get their jobs done well and on time.

I had a great networking meeting yesterday along with Tami Forman, the CEO of our non-profit affiliate Path Forward, and Joanne Wilson, my board co-chair.  It was a meeting that Joanne set up that the three of us had been talking about for over a year.  Joanne made a great comment as we were debriefing in the elevator after the meeting that is the foundation of this post.  Tami and I shaped her comment into this metaphor:

Finding wood to help start a fire is different from pouring gasoline on a fire

As an entrepreneur, you need to constantly be asking for help and networking.  Those meetings will shape your business in ways that you can never predict.  They’ll shape your thinking, add ideas to the mix, kill bad ideas, and connect you to others who can help you in your journey.

But you need to have a good sense of who to meet with, and when, along the way.  Some people, you can only meet once, unless they become core to your business, so you have to choose carefully when to fire that one bullet.  Others will meet with you regularly and are happy to see longitudinal progress.  Regardless, being clear on your ask is critical, and then backing up from that to figure out whether this is the one bullet you can fire with someone or whether it’s one ask of many will help you figure out if you should push for that networking meeting or not.

Why?

Because asking someone to help you find wood to start a fire (the early stages of your business) is different from pouring gasoline on an existing fire (once you’re up and running).  If you’re in the super early stages of your business and looking for product-market fit, you won’t want to meet with people who aren’t conceptual thinkers, who aren’t deep in your space, or who might only see you once.  Maybe they can help you brainstorm, but you’ll find better partners for that.  They might be able to provide concrete help or introductions, but you’re probably not ready for those yet.  It’s a waste of time.  You need wood to start your fire, and people like this aren’t helpful scouring the forest floor with you to find it.

However, those people can be fantastic to meet with once you have product-market fit and are deep in the revenue cycle.  You have clear demonstration of value, customer success stories, you know what works and what doesn’t and why.  You can have short, crisp asks that are easy for the person to follow-up on.  They will be willing to lend your their name and their network.  You have a fire, they have a cup of spare gasoline, and you can get them to pour that cup on your fire.

The judgment call around this isn’t easy.  Entrepreneurial zeal makes it abnormally comfortable to call on any stranger at any time and ask for help.  But developing this sense is critical to optimizing your extended network in the early years.

This is another big week for us at Bolster. On the heels of the announcement we made last month about our Series B financing, we are now announcing the launch of a new program called Bolster Prime and a new venture capital fund called Bolster Ventures. These are important steps in Bolster’s evolution and in the fulfillment of our mission, what we call internally our “Big Idea,” which is to empower the innovation economy.  

The roots of Bolster Prime and Bolster Ventures pre-date the founding of Bolster. In our prior lives, the Bolster founders worked together to scale up a business called Return Path and also 

worked as advisors and mentors to numerous early stage founders and startups. One of the things we noted in our very first post, now part of the About Us section of Bolster.com, was:

After exiting Return Path [the company where our founding team worked for many years], we wanted to do for others what we did for each other as a seasoned executive team. We wanted to know: “How could we help other CEOs, executives and boards bolster themselves to go the distance and scale with their organizations?”

While the founding team was exploring potential business opportunities that allowed us to make a bigger impact on the world, Silicon Valley Bank and High Alpha Innovation were together envisioning a platform to help VC-backed portfolio companies more effectively navigate the complex world of executive talent needs. When our three groups came together, we realized we shared a vision to build a company that puts people first in all aspects to drive high-growth businesses.

I’ve never written before about those other “potential business opportunities” that our team was exploring along with our prior investment syndicate, Fred Wilson from Union Square Ventures, Greg Sands from Costanoa Ventures, and Brad Feld from Foundry. The one our team was particularly excited about was a concept we were calling at the time “Venture Acceleration Partners.” The key points in the pitch deck we created were:

• There is a gap in the market of investors adding “management” value to portfolio companies between Accelerators/Incubators/Studios at the low end and Private Equity firms and very large VCs at the high end. What about the middle?
  
• “The middle” consists of venture-backed companies that are neither early stage nor mature. They are typically founder-led, often by a first-time CEO with new or incomplete management teams who need a lot of mentorship/development, and with a diversified cap table of firms that don’t own operating or consulting practices to help guide the scaling process.
  
• These companies tend to have consistent and stage-unique challenges around scaling execution across every aspect of the business.
  
• By creating an advisory firm made up of seasoned operators, we can quickly identify the risk areas and provide mentoring, guidance and execution to management teams for defined periods of time to keep them on the right track and increase their companies’ performance.
  
• We want to create a firm that has enough skin in the game to have long-term relationships with management teams…and that doesn’t charge (much) for services because incentives are aligned as a co-investor.

Our original deck envisioned a firm that was sort of a hybrid of a “McKinsey for startups” and a venture investor. When I shared that pitch deck (and two other ones I’ll save for another day), with my long-time friend Scott Dorsey from High Alpha, he responded by sharing with me a related pitch deck he was working on with corporate partner Silicon Valley Bank out of the High Alpha Studio for a talent marketplace. We immediately looked at each other and said “we should put all of these ideas together with this founding team, High Alpha and SVB, and the Return Path investors, and change the way startups connect with talent.” That’s what we did, and we almost immediately started building the first part of the Bolster business, which was the talent marketplace.

About six months into our journey building Bolster, I was talking to Brad and reminded him that I was interested in bringing the Venture Acceleration idea to life now that we had a vibrant talent marketplace up and running at Bolster. 

Standing up a new program of this magnitude with limited resources at the same time as building a new venture capital firm from the ground up, on top of a still pretty brand new startup – that felt like a tall order, even for a large and senior founding team like ours. We needed another senior leader to join our team. 

Brad’s visceral response in this conversation was a very clear, “you should hire Jenny.” Enter Jenny Lawton. Jenny is someone I’d known peripherally for many years as a mutual friend and colleague of Brad, but we weren’t particularly close. We agreed to meet for breakfast at a diner halfway between our houses at a time in the pandemic when there wasn’t a whole lot of in-person meetings going on. 

As Jenny’s written about this week, it was the right call at the right time – we had a full meeting of the minds about the role mentorship plays in supporting entrepreneurs, the unmet needs of entrepreneurs even with all the support out there from accelerators and investors, and the desire that both of us had here in the back half of our careers to, as Steve Jobs would say, “make a dent in the universe.” Jenny’s experience as a multiple-time senior executive and startup advisor (including four years as the COO of Techstars) was a perfect match for us. She joined our team pretty quickly, first fractionally (the Bolster way, right?), then full-time in the middle of 2021. 

And the rest, as they say, is history. Working as part of the Bolster leadership team this past year, Jenny has spearheaded the creation of Bolster Prime, from selling and mentoring the first few clients personally, to designing the curriculum and programmatic learning, to figuring out the right positioning and pricing to developing the recruiting strategy for the program. We’ve worked together and along with the rest of the team at Bolster to bring in an amazingly talented group of experienced former and current CEOs and other senior operators as our first group of mentors.  Any entrepreneur would be lucky to have one of these mentors in their corner. We’ve now raised a venture capital fund as first-time fund managers from our own investors and our program’s mentors, all of whom believe in the power of Bolster as the next generation platform to help empower the innovation economy. 

Most good ideas swim in a sea of comparables. There are now a handful of other firms out there that combine advice for entrepreneurs with capital. But we believe our model, with thousands of Bolster Member CXOs already on board, is unique. Bolster Prime and Bolster Ventures, powered by Bolster’s on-demand talent marketplace, is here to help early stage founders reimagine the way they scale up their leadership teams, their boards, and themselves. We are changing the way the startup game is played. Come take a look and see what’s in it for you.

(This post is running concurrently on the Return Path blog.)

It is now widely understood that the Internet runs on data. I first blogged about this in 2004—14 years ago!— here.  People have come to expect a robust—and free!—online experience. Whether it’s a shopping app or a social media platform like Instagram, these free experiences provide a valuable service. And like most businesses, the companies that provide these experiences need to make money somehow. Consumers are coming to understand and appreciate that the real cost of a “free” internet lies in advertising and data collection.

Today, the Wall Street Journal ran an article exploring the data privacy practices of Google and some of the third party developers who utilize their G Suite ecosystem. Return Path was among the companies mentioned in this article. We worked closely with the journalist on this piece and shared a great deal of information about the inner workings of Return Path, because we feel it’s important to be completely transparent when it comes to matters of privacy.  Unfortunately, the reporter was extremely and somewhat carelessly selective in terms of what information he chose to use from us — as well as listing a number of vague sources who claimed to be “in the know” about the inner workings of Return Path. We know that he reached out to dozens of former employees via LinkedIn, for example, many of whom haven’t worked here in years.

While the article does not uncover any wrongdoings on our part (in fact, it does mention that we have first-party relationships with and consent from our consumers), it does raise a larger privacy and security concern against Google for allowing developer access to Gmail’s API to create email apps. The article goes on to explain that computers scan this data, and in some rare cases, the data is reviewed by actual people. The article mentions a specific incident at Return Path where approximately 8,000 emails were manually reviewed for classification. As anyone who knows anything about software knows, humans program software – artificial intelligence comes directly from human intelligence.  Any time our engineers or data scientists personally review emails in our panel (which again, is completely consistent with our policies), we take great care to limit who has access to the data, supervise all access to the data, deploying a Virtual Safety Room, where data cannot leave this VSR and all data is destroyed after the work is completed.

I want to reaffirm that Return Path is absolutely committed to data security and consumer data privacy. Since our founding in 1999, we’ve kept consumer choice, permission, and transparency at the center of our business. To this end, we go above and beyond what’s legally required and take abundant care to make sure that:

1. Our privacy policy is prominently displayed and written in plain English;
2. The user must actively agree to its terms (no pre-checked boxes); and
3. A summary of its main points is shown to every user at signup without the need to click a link

While a privacy expert quoted in the article (and someone we’ve known and respected for years) says that he believes consumers would want to know that humans, not only computers, might have access to data, we understand that unfortunately, most consumers don’t pay attention to privacy policies and statements, which is precisely why we developed succinct and plain-English “just-in-time” policies years before GDPR required them. When filling out a form people may not think about the impact that providing the information will have at a later date. Just-in-time notices work by appearing on the individual’s screen at the point where they input personal data, providing a brief message explaining how the information they are about to provide will be used, for example:

It’s disappointing to say the least that the reporter called this a “dirty secret.”  It looks pretty much the opposite of a secret to me.

In addition to our own policies and practices, Return Path is deeply involved in ongoing industry work related to privacy. We lead many of these efforts, and maintain long-term trusted relationships with numerous privacy associations. Our business runs on data, and keeping that data secure is our top priority.

Further, I want to address the scare tactics employed by this journalist, and many others, in addressing the topics of data collection, data security, and who has access to data. It’s common these days to see articles that highlight the dangers that can accompany everyday online activities like downloading an app or browsing a retail website. And while consumers certainly have a responsibility to protect themselves through education, it’s also important to understand the importance of data sharing, open ecosystems, and third party developers.  And more than that, it’s important to draw distinctions between companies who have direct relationships with and consent from consumers and ones who do not.

While they may not be top of mind, open ecosystems that allow for third-party innovation are an essential part of how the internet functions. Big players like Facebook and Google provide core platforms, but without APIs and independent developers, innovation and usability would be limited to big companies with significant market power and budgets—to the detriment of consumers. Think about it—would Facebook have become as wildly popular without the in-app phenomenon that was Farmville? Probably, but you get the point: third party applications add a new level of value and usefulness that a platform alone can’t provide.

Consumers often fall into the trap of believing that the solution to all of their online worries is to deny access to their data. But the reality is that, if they take steps like opting out of online tracking, the quality of their online experience will deteriorate dramatically. Rather than being served relevant ads and content that relates to their browsing behaviors and online preferences, they’ll see random ads from the highest bidder. Unfortunately some companies take personalization to an extreme, but an online experience devoid of personalization would feel oddly generic to the average consumer.

There’s been a lot of attention in the media lately—and rightfully so—about privacy policies and data privacy practices, specifically as they relate to data collection and access by third parties. The new GDPR regulations in the EU have driven much of this discussion, as has the potential misuse of private information about millions of Facebook users.

One of Return Path’s core values is transparency, including how we collect, access and use data.  Our situation and relationship with consumers is different from those of other companies. If anyone has additional questions, please reach out.

Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling.

You won’t have a ton of time to engage with the Chief People Officer but there are a few ways where I’ve typically spent the most time, or gotten the most value out or my interactions with them. So, you’ll need to capitalize during those few moments when you do get a chance to engage with the Chief People Officer.

I ALWAYS work with the CPO as a direct report.  No matter who my HR leader is, no matter how big my executive team is, no matter how junior that person is compared to the other executives. I will always have that person report directly to me and be part of the senior most operating group in the company.  That sends the signal to everybody in the company that the People function (and quite frankly, diversity, culture, and a whole host of other things) are just as important to me as sales or product. I guess that’s walking the walk, not just talking. If I’m not serious about diversity, about our core values, and about the people in the company, no one else will be either. So, I always have the CPO as a direct report.

A second way to engage with the CPO is to insist on hearing about ALL people issues. First, I am a very “retail-oriented” CEO, and I like to engage with people in the business—at all levels, in all departments, and in all locations.  So I like know what’s going on with people — who is doing particularly well and about to be promoted, who is struggling, who is a flight risk, who is going through some personal issue (good or bad) that we should know about. This isn’t prying into people’s lives, but a real way to engage with people beyond business and a way to show that you care about them as a person. Even more than just me wanting to be in the know, I want others in the company to have a deep level of awareness of our contributors. For example, in our Weekly Sales Forecast meeting at Return Path, because our head of People knew that I wanted to know about all these details on our employees, they insisted that all the other People Business Partners roll those issues up as well. That means everybody in the room was in the know as well.  It’s not just to have a better understanding of people, there’s a business case for knowing what’s going on at a very detailed level and the number of issues we nipped in the bud, the number of opportunities we were able to jump on to help employees over the years because of this retail focus, has been immense.

I also engage with the CPO as an informal coach for myself and with my external coach.  In an earlier post I mentioned that a great Chief People Officer can—and should—call a CEO out when a CEO needs to be called out.  And that also means that great Chief People Officers engage with CEOs deeply about how they are doing, they help CEOs process difficult situations, and help them see things they might not otherwise see.  Being a CEO is a lonely job sometimes, and it’s good to have a People partner to be able to collaborate with on some of the most personal and sensitive issues.

Finally, I engage with the CPO to design and execute Leadership/Management training.  This is an important skill that a great CPO brings to the company and I have found that it is the best way to create a multiplier effect of employee engagement and productivity. The CPO in your organization needs to teach all leaders and managers how to be excellent at those crafts — and how to do them in ways that are consistent with your company’s values.  This is a tall order for one person to put together so I always took a lot of time, in large blocks of hours or days, to either co-create leadership training materials and workshops with my head of People, or to lead sessions at those workshops and engage with the company’s managers and leaders in a very personal way.  That always felt to me like a very high ROI use of time.

(You can find this post on the Bolster Blog here)

One of the most common things early stage CEOs say to me once they find product-market fit and make a few sales is “I need a CRO.” The answer is almost always, “no, you don’t.” A couple years ago I wrote about the evolution of enterprise selling organizations in this post. Reading that is a good place to start this topic. Go ahead…I’ll still be here when you come back.

Welcome back!

So in the early days of a company, it’s all “selling on whiteboard.” The need that early stage CEOs have that prompts them to tell me they need a CRO is simple the need to have help selling.

What the CEO really needs is a couple of very good early stage sales reps. People who are senior enough and clever enough to hold clients’ attention. People who are junior enough to accompany the CEO or other founders on dozens of “selling on whiteboard” sessions with clients to be able to start doing that work on their own. And People who can help the transition from “selling on whiteboard” to “selling on Powerpoint” by doing some very basic documentation of the selling process, buying centers, influencers, and value proposition.

It may also be true that the CEO doesn’t really know much about sales — maybe it’s a technical founder, or even a founder who came up through marketing or product management — and that part of the “I need a CRO” comment is really just an admission that the CEO doesn’t really know how to structure and manage a sales effort. In that case, my first suggestion is that the CEO read the excellent Startup Sales section within Startup CXO. And if that’s not enough, then there are over 1,200 fractional CROs in the Bolster marketplace who can give you anything from an hour of consulting to a couple days per week as a fractional executive to help you put some structure in place for your new sales reps. Once you have a repeatable sales motion, you can hire more reps and a Sales Manager/Director or VP.

So no, you don’t need a CRO. But there are lots of things you can do to get the help you need in the early days of selling that are less expensive, less risky, and a better fit for early stage companies.

We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.

Episode 1: 3 Tips to Scale Your Culture with Nick Mehta

Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many? Nick and I discussed what happens to company culture when you achieve your scaling and growth goals.

Episode 2: Managing Up with Cristina Miller

Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Cristina Miller—a seasoned, results-driven executive and board member (including on Bolster’s board!) with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.

Episode 3: Common Mistakes Founders Make with Fred Wilson

Fred Wilson has been a venture capitalist since 1987 and has worked with me for over 20 years now—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. Listen to this episode to learn how to recognize and avoid those mistakes for yourself.

Episode 4: Cultivating Talent to Promote Internally with Nick Francis

In this episode, Nick Francis—co-founder and CEO of Help Scout—joins me to discuss what it takes to cultivate in-house talent and embody organizational values. I talk about my playbook for building effective teams and developing leaders with a growth mentality as part of this.

Episode 5: Deep Dive with Jeff Epstein

Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator (and one of my former board members) Jeff Epstein joined me for an extended episode about the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. Tune in to follow the shifts in Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.”

Episode 6: Hallmarks of Successful Founders with David Cohen

David Cohen, Founder and Chairman at Techstars, shares the top three signs he looks for that differentiate successful founders—things that are nearly impossible to fake. Either you have them, or you don’t. This one is awesome.

Episode 7: Success as a Fractional Exec with Courtney Graeber

If you know anything about Bolster, you know we’re a champion for fractional executives. As an Interim Chief People Officer, HR Executive Consultant, and trusted mentor to executive teams, Courtney Graeber provides feedback and recommendations that enhance organizational culture and attract, develop, and retain top talent. Many of her clients are navigating transitional periods—and that’s where Courtney’s expertise comes in. Listen in to learn what it’s like to be (or work with) a fractional head of people.

Episode 8: 3 Ways VCs Say “No” Without Saying “No” with Jenny Fielding

It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says one of NYC’s top pre-seed investors Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either.  Here, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.

Episode 9: Building a Strong Culture with Jailany Thiaw

Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines, joins me to discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.

Episode 10: Deep Dive with Brad Feld

Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur who I’ve also worked with for more than two decades. In this episode, he and I take a deep dive into how startups and venture capital have changed over the past 25 years—and what has stayed the same.  They also discuss the dynamics of startup boards, along with common characteristics that make founders or companies successful at scale.

Episode 11: The Value of Podcasting with Lindsay Tjepkema

This episode is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers.  She and I dive into the reasons why podcasts are such a great way to get your voice—literally—out into the world. Tune in to hear Lindsay’s tips for starting a podcast as a CEO, setting expectations, asking meaningful questions, and creating human connection. We’ve loved partnering with Lindsay and her team so far on The Daily Bolster!

Episode 12: Interviewing for “Culture Fit” with Rory Verrett

What does it mean to interview for culture fit? How should CEOs and leaders go about doing it—and is there a better way? Rory Verrett is the founder and managing partner of Protégé Search, the leading retained search and leadership advisory firm focused on diverse talent, and is also on Bolster’s Board of Directors. He and I discuss why CEOs are not always the best arbiters of company culture, then we dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.

The Daily Bolster is for people in the startup world want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed. Instead, we’re getting straight to the point with mostly 5-minute episodes. Any and all feedback welcome!