An Interview with James Cham, Partner, Bloomberg Beta

James Cham is a venture capital investor with Bloomberg Beta, a firm focused on investing in the future of work. James invests in companies working on applying machine intelligence to businesses and society. Prior to Bloomberg Beta, James was a Principal at Trinity Ventures and a VP at Bessemer Venture Partners, where he focused on consumer services, enterprise software, digital media; and served on the boards of CrowdFlower, Open Candy, LifeLock, ReputationDefender, Sonic Mule, and BillShrink. He was previously a management consultant at The Boston Consulting Group and a software developer. James received an MBA from MIT's Sloan School of Management and Computer Science degree from Harvard.

How did you get into the world of Venture Capital?

After the startup that I was a part of got acquired, I went to business school. A good friend of mine introduced me to a firm called Bessemer, where I got my introduction to venture capital and how I ended up investing in startups.

And before Venture Capital you were a software developer?

That's right, I was a software developer in the late 90s to early 2000s. I was part of that transition from client-server over to web-based, enterprise applications, and I wrote a bunch of mediocre code and made a bunch of bad design decisions that other people suffered for as a result. So I’ve been through enough cycles to least understand what that feels like from a potential customer perspective.

Why did you invest in LaunchDarkly?

Let me take a step back. When we raised money from Bloomberg to start the fund nearly five years ago, one of the core claims was that we are living in a world where everyone's a knowledge worker. In that world, we should look at the best knowledge workers around. We should copy their techniques to find ways for them to scale what they're doing. And of course, the best knowledge workers in the world are software developers. This is in part because some of the best software developers are a mix of lazy and smart -- they spend all their time avoiding working on applications and instead work on frameworks and systems infrastructure. So broadly, that is what we’re excited about.

LaunchDarkly is exciting for two core reasons: One, there was an immediate sense of recognition of a problem. When I first heard Edith pitch the idea, I thought “Oh my goodness! I wish this existed when I was being yelled at as a software developer or when I was managing projects.” There's a sense that this should exist and this is the right way to do something. I think most software developers do this. You build your own bad bug-tracking system or slightly lame issues-tracking system. And I had done something like a features flag product for some other project, but I didn't call it that. There was a sense that Edith understood this and saw this more clearly than I did. That’s one excitement.

And then there's the other reality which is the excitement of seeing a leader like we did. There's a point when you meet her and say, “Oh, she's not just someone who has built something interesting, but she’s someone you can see leading something important.” That’s another important part of what made it exciting for me. As I've gotten to know her better, that’s only been validated more and more.

You met LaunchDarkly through Alchemist. What are your thoughts of Alchemist in general?

The thing that is most helpful about Alchemist is that it’s more systems driven. The people around it are quite credible and thoughtful. You look at the set of advisors: These are people who aren’t really famous and lightly involved, but rather accomplished and very deeply involved. From my perspective, that makes the process of diligence and validating people much easier.

There’s always a sense about Alchemist that you’re being as positive as possible about the opportunity, but at the same time you don’t lie. That's an important thing for an investor and really helpful.

What is the approximate size of your fund? How does that compare to other funds in a similar stage?

As the markets are fragmented, even in the earlier stage, judging how we compare to other funds does become more complicated. But the core physics of our first fund was $75M, and the second fund is also $75M. Our first check sizes range between $100K to $1M, and we participate anywhere from friends and family rounds to right before the Series A.

Does your fund have a specific vision or focus? I know you've touched on the future of work prior, but is there more to that?

We talk about the future of work, in part, because historians of science would say that it takes two generations of managers for any new technology to really make an impact on the economy. At the start of our fund, we were twenty years into the Web -- networked computers, which is another way to think about it. We were convinced that it is only now we’ll see massive changes in the way people work, because now you have a bunch of people creating businesses that are suited for the Web.

Within that vision, we have a focus both on productivity for knowledge workers -- we see a lot of opportunities to integrate and learn from developers -- and the way software ends up changing the way that people do business. New tools will be required to support this new kind of business, which include developer tools up to enterprise software.

We also believe that machine learning, model building, and AI in general are different than normal software development. I think they have profound implications that we haven’t understood yet, not just on all the cutting edge research we’ve done, but especially around the way that people make good software and machine learning models. Machine learning model building is different than software development. The economic characteristics are different, meaning machine learning will give rise to new business models. So somewhere out there, there’s going to be a person that is the Bill Gates or Marc Benioff of machine learning. They are going to do a mix of marketing, technical, and product insights and come up with a different way of providing machine learning or AI-driven businesses in a different light. They are going to charge in a different way or sell it in a different way. That’s the innovation or change in the way that people do business that we’re most excited about, and where we spend a lot of time.

How does your fund differentiate itself from other funds?

On the one hand, the money is a commodity. The money is the same, and so the way you differentiate is you bundle different services along with it. Some of that is the personality of the partners and the way that they relate to other people. A part of that is also a set of things that we focus on. I think, we think through more than other firms ways that founders can make a dent in the universe through the way they talk about themselves. On that side, we’ve thought a lot out. And we work with our companies a lot around that.

So much of it depends on the specific relationship that each partner has with the founder that that investor has invested in, especially at the seed stage. There aren’t magic formulas.

How do you individually differentiate yourself from other individual VC’s?

The right way to compete along those lines is not to compete. Instead, I’m most interested in angles that people aren’t thinking about yet. And I’m most interested in thinking through angles that are poorly understood.

So if someone has just another generic SaaS company that’s growing at a certain percentage, then I'm probably not the right person for them. An old friend of mind would say that there’s two types of VCs. There are VCs that if they weren’t VCs, they’d be bankers, and others who are VCs because they spent too much time pitching. I’m definitely part of the second camp. There are a whole set of ideas that should be enabled and would be if someone stuck their neck out and said they believed this founder could create something special and make the world better. And that’s what I try to do.

​What makes an investment compelling for you? Is there something in particular that makes an investment more compelling than not?

There are all the things that people talk about: traction, the team’s experience, potential, etc. I think those things are all really important, but the thing that might be under appreciated is that core insight. Sometimes the founders don't understand what the core insight is. There is nothing quite as exciting as sitting with a founder and discovering together what actually makes them special. And oftentimes that core insight can be communicated in a paragraph or it could take a lifetime to get there. For me, that’s what I'm looking for that. It’s going to be in areas where I have enough preconceived notions that someone could surprise me.

What is the number one red flag for you that would make you pass on an investment?

The moment I feel like I can’t trust someone is probably the number one reason why. When it’s close or we thought we should have invested, that tends to be the number one surprising thing about most folks that we pass on. Investing in a company is not something you take lightly. We take it very seriously and it’s a relationship we take very seriously as well.

What separates the great founders who get an investment from you vs. the good founders who don't quite make the cut?

There’s a way in which the best founders help you believe. Whether it’s helping the investors believe or first customers or the first employee or the co-founders. And that way of getting someone to believe, it comes in all sorts of ways. It’s not generic. It comes in many sizes and forms, but that ability to impose your will on the universe. It only works if you can convince other people.

Would you be more likely to fund a very experienced team with a mediocre idea or a team of novices with an amazing idea?

Nuance matters a lot here. I think that there are plenty of times when the very smart, experienced team can take a mediocre, initial idea and because they are so customer-oriented or technically visionary that they end up building something better, smarter, or more interesting. However, generically, I hunt for people who have extraordinary insight and how they get there. The insights do not have to manifest themselves with the first product, but they manifest themselves somehow that makes them extraordinary.

Is there any piece of advice you would give founders who are fundraising that you think does not get shared enough?

I think founders forget how much power they have in a situation. There are cycles that founders get in where they end up feeling like this is just another boring sales call. But what the founders are doing is they're sharing their most precious things. They're sharing things that they probably care more about than almost anything else in the universe. When they pitch, they should treat it that way. That investors are lucky to get a view into this. The moment the founder forgets that, humans can smell it. You have to continue to be resilient and continue to believe because investors, although we do it through a financial instrument, at the core, we’re declaring we have faith in someone and we have enough faith that we’re putting our money and our goodwill behind it.

If you think about Edith and the way that they were together and the way that they communicated and seemed to take what they do seriously, even when things are difficult, that’s the sort of thing that an investor is looking for.

What areas are you excited about now and in the future?​

I’m excited for when things that we call AI-related start being machine learning-related and get boring. When everyone understands how to engineer a bunch of problems, things get boring, and that's when you end up with a lot of product innovation. I’m very excited about that!

An Interview with Edith Harbaugh, CEO, LaunchDarkly, Alchemist Class 8 (Ocho)

CEO and co-founder of LaunchDarkly Edith Harbaugh has raised over $30M in funding from investors at Uncork, DFJ, and Redpoint. She has more than 10 years of experience in product, engineering and marketing with both consumer and enterprise startups. Edith was Product Director at TripIt, where she launched TripIt for Business and ExpenseIt. She holds two patents in deployment. Edith earned a BS, Engineering from Harvey Mudd College and a degree in Economics from Pomona College. She enjoys trail running distances up to 100 miles.

5 Tips To Help You Navigate The Procurement Process Like A Pro

As a founder and mentor, I begin each week with pipeline meetings and the question: “What are the barriers to close?” I teach this method to Alchemist startup founders to help them identify the barriers that can stall each deal. Too many first-time founders provide a forecast to potential investors without allowing for the possibility that procurement may stall or kill their deal. A deal is not done until it is signed. Here are 5 best practices that will help you navigate the procurement process like a pro.

Seed Fundraising - How to get “Reservations” from Angel Investors

At the beginning of your seed fundraising process, you may have to wait several weeks for the first “yeses” from any investor. During this time, if you’re not getting any commitments your round can appear stagnant. Reservations from Angel investors can help solve this problem; as your round’s availability decreases it will put pressure on other investors to say yes.

Here’s how to secure the reservations:

Ask for Money

Most Angel investors turn down 90% of the meetings founders request, so if you get a meeting, you must directly ask if the investor is interested in investing.


1. Wait until 10 minutes before the end of the meeting, then ask if they have any questions. For example:

“That’s a quick overview of AcmeCorp - do you have any questions?”

2. When you’ve completed the questions and/or when there’s 5 minutes left, ask if they want to talk more about investing. For example:

“Does AcmeCorp fit within your investment thesis?”

“Is this investment something you might like to be a part of?”

“Would you be interested in investing in our current round?”

Ask Usual Check Size

If the investor expresses interest, the next step is to find out their usual check size. This will be an integral part of the reservation later.


1. After the investor expresses interest, ask about their investment process, as this will give you an idea of the time they take to make a decision, as well as their usual check size. For example:

“What’s your usual process for investments like this?”

2. If they don’t reveal their check size, you’ll have to ask directly. For example:

“What’s your usual check size for these investments?”

“What size of investment are you considering here?”

“Do you have a fixed amount you usually invest at this stage?”

Secure the Reservation

Once you know the investor’s potential check size and when they will decide (roughly), it’s time to secure the reservation.


1. If the investor’s check size, decision timeline, and other requirements fit with your plan, tell them you’d be open to having them involved. For example: “I’ve enjoyed our conversation and your approach seems to fit with our current raise”

2. Next, acknowledge they will need time (and perhaps further materials) to decide and ask for the reservation. This step is critical. For example:

“Should I hold that space for you while you’re deciding?”

“I will hold your spot, to give you some time to decide.”

“I usually hold space for investors while they’re in diligence, I’ll do the same for you.”

Once you’ve promised to reserve space for an investor, it would be wrong to give that space to another investor without fair warning. Thus, your round’s availability is reduced and all other potential investors start to feel the pinch of FOMO (fear of missing out). When new investors now ask for your fundraising status, you can respond with spoken for availability for example:

“We’re raising $500k and have 50% spoken for”

Practice these phrases before the meeting, and the early part of your seed fundraising will be much easier.

Thanks to Kaego Rust for her help on this article.

About Ash Rust

Ash Rust is a Partner at Alchemist and the Managing Partner of Sterling Road. You can find more of his writing about Seed Fundraising on Medium.

About the Alchemist Accelerator
Alchemist is a venture-backed initiative focused on accelerating the development of seed-stage ventures that monetize from enterprises (not consumers). The accelerator’s primary screening criteria is on teams, with primacy placed on having distinctive technical co-founders. We give companies around $36K, and run them through a structured 6-month program heavily focused on sales, customer development, and fundraising. Our backers include many of the top corporate and VC funds in the Valley—including Khosla Ventures, DFJ, Cisco, and Salesforce, among others. CB Insights has rated Alchemist the top program based on median funding rates of its grads (YC was #2), and Alchemist is perennially in the top of various Accelerator rankings. The accelerator seeds around 75 enterprise-monetizing ventures / year. Learn more about applying today.

An Interview with Toni Schneider, Founding Venture Partner, True Ventures

A Swiss native who studied computer science at Santa Barbara City College and Stanford University, Toni Schneider started his career as a software engineer working on NASA virtual reality simulators. He went on to become a startup founder and CEO, and an executive at Yahoo!, before joining the True team as a founding Venture Partner. Toni is well known for his role as CEO of Automattic, the company behind He helped WordPress become a globally known brand that powers over 30% of all sites on the internet. For his work, Toni was recognized at the Crunchies as CEO of the year.

When he is not running one company or advising another, you can find Toni in his VW van crossing the US with his family, coaching San Francisco Little League baseball, or tinkering with old cars.

How did you get into the world of venture capital?

I got into it first as an entrepreneur and founder, raising money from VCs. I did that for three startups. Then I switched to VC while also still being CEO of a startup. True Ventures is the only VC firm I’ve ever been with. One of True’s co-founders, Phil Black, was a close friend of mine. He was thinking about starting a new VC firm and asked me if I would be interested in being part of it. So when he started True together with Jon Callaghan, I said yes and dove in to learn from them how to raise money from limited partners and make venture investments as we pulled together True’s first fund in 2006.

That’s so interesting to be on both sides. You began on the entrepreneurial side pitching to VCs and now you are a VC. How do you think that transition helped prepare you? Does it help you identify what you are looking for in a company that you want to fund? What a red flag would be, that sort of thing?

It's probably both good and bad. The good part is that I was able to bring a founder’s perspective to how we structured True. Our goal was to be very founder friendly. I could share honestly what it was like to sit on the other side of the table from a VC. That helped in creating a firm where we really think of founders and entrepreneurs as our customers and where we do everything we can to provide a good service to them.

Another advantage is that when I look at startup teams, I have a good hands on feeling for their abilities because I’ve run several startups and hired and managed many startup teams.

The disadvantage is that it comes with biases. I had a certain experience as an entrepreneur and certain things that worked for me and certain things that failed. That very much shaped my thinking around startups. While it gives me a good point of view, I also have a harder time going outside of my own experience and being open to different approaches to starting businesses.

What for you personally makes a startup look like a good idea? What is something compelling to you as a startup you would fund?

For me it always starts with the team. I look for strong founder qualities, which in my mind are the ability to be very charismatic, and to have a really exciting, big, long term vision combined with flexibility when it comes to everyday execution that's going to be very zig-zaggy for a startup. There will be new challenges every day. So you look for somebody who's comfortable asking for help and being adaptable near term, but has an audacious long term vision that they don't waver from. The charisma and communication skills will help attract a lot of people to their startup.

Finally, someone who has a lot of depth in their area of expertise. This is something I always look for. As I dig into an idea, do I feel, “Wow, this person is three steps ahead of me and has really thought it through and knows everything about the space they’re about to get into”? Any good idea is going to have more than one team chasing after it, and I want to bet on the team that has a lot of depth.

There's a lot of emphasis for future founders on idea generation, but it honestly sounds like the idea comes second to more of the team, from what I just heard you say...

First step is to be in the right place at the right time for your skillset. There are other factors that play into it, but without the right people, none of it is going to work.

The second step is the product and the idea. The product needs to be unique and truly compelling and have a story that can be articulated in a simple way. What does the product do? Who is it for? What makes it unique? It's surprising how often founders can’t answer those three basic questions in a straightforward manner. I want to invest in a product that gets me personally excited, that I believe will have a positive impact on the world, and that will make customers say, “Wow, I want that, that’s different. That’s a totally new approach.”

For the third step, like everybody else in the VC business, I look at the market. Is this something that if it works out - there can be a ton of risk associated with, frankly we want a ton of risk - but if it works out, could it be a very big business? Is it a big market that seems ready for a massive change? That has to be in place as well, otherwise you can have an amazing team with an amazing product, but without big growth and revenue potential it won’t be a VC scale opportunity. That's not what we’re in business for.

What was the number one red flag that would caution you away from investing in a team or a startup?

On the people side, it's teams that don't seem to have the right chemistry or the right understanding of what their roles are going to be, or teams that don't have a track record together. That for me is maybe not a red flag, but definitely a yellow flag.

The biggest red flag usually comes up during initial due diligence. It happens quite a bit that I'll think “Wow, this is a really good idea, I'm going to dig in,” and when I do, I realize that there are already a bunch of teams doing the same thing and the idea quickly doesn't seem so original. It feels like more of a rehash or tweak of another idea. That usually throws cold water on a project for me. That’s the biggest red flag, that an idea isn’t that unique.

It's only one percent of startups go on to become really big. You really do have to filter out ones that you don't think are capable or have a clever idea.

Yes, and even when everything fits, even when you check all the boxes that I just described, it's still hard. Because nothing ever plays out exactly the way we plan and hope. Another filter we use at True is that we focus on one type of deal. We do two to three million dollar seed rounds. That’s it. If it’s something that is a really good idea with a good team, but two to three million dollars is not enough to get it off the ground or it’s already past the seed stage, we won't do it even though it might be a great opportunity. We are really trying to stay focused on one stage of investing, do it well, and have a whole portfolio of companies that go through the same stage so they can all learn from and support each other.

Seems like True has a specific focus on seed round innovative companies, what else do you look for?

We’re not thesis investors. We don’t have certain sector or certain type of business that we look for. We’re not a “SaaS fund” or a “Crypto fund”. We invest behind great founders and then double down when things are working. For example, we were early investors in Fitbit, a couple of years before hardware startups and connected devices became a trend. We weren't looking for that trend, we just liked that team and particular idea, and when we saw it working for them, we followed on with a bunch more hardware investments like Ring and Peloton. We follow wherever our founders take us. Recently, we've invested in robots, satellites, and biotech, which are all new areas for us. We try to be very open-minded about what the subject matter might be.

You really do try to treat founders and startups that work with you very well. Is that how your fund differentiates from others? There are certainly quite a lot of VC funds around here.

One thing that makes us different is that we invest earlier than the majority of VCs. We're really close to an angel stage, but we're a full service VC firm. We are there in the very beginning, often when it’s just two or three people with an idea, and we have our founders’ backs all the way through. Most VC firms want to see revenue traction and product-market fit before they even look at something.

The second thing we do that differentiates us is we are focused on the personal needs of a founding team, not just the business needs. We know what you will need as a founder, as a leader, to get really good at your job, to get through the ups and downs of doing a startup. If something goes wrong, we want to be your first phone call. We don't want to be the kind of investor where you feel like, “Oh God, something went wrong, how do I break this to my investors? I don't want to talk to them.” We hope to have a trusted relationship so that even when things don't go well, we're going to be there and help you through it.

Part of how we do that is to connect all the founders within our portfolio and they help each other improve. That's our founder network and platform. We have events and tools that facilitate direct, open, and honest collaboration. It’s optional, but most of our founders take advantage of this amazing peer network. I think it’s super valuable and quite unique among VC firms.

What made you to want to invest in Laura and her startup, Atipica? What made them stand out from the pack of other investments you were evaluating at the time?

Laura and Atipica really hit a lot of the boxes I mentioned earlier. She’s a very charismatic founder with a big vision, a great communicator with deep knowledge in the area of diversity, inclusion and hiring. She had spent several years working on the idea and product, talking to a lot of companies about their needs, so she had depth of expertise. We started working together a little bit over two years ago. It was still early days in diversity and inclusion tools and she was well ahead of many of the people we talked to. She had a small team, pre-revenue but she already had some pilot customers. So it was the right stage for us and we felt like our seed investment could help her build out her team, get the product launched, and get to the next stage.

The hiring and recruiting sector in particular was interesting to us at the time. We had just had a successful exit to LinkedIn with Connectifier, and I was and still am on the board of another investment we made in this space called Handshake. They’re in the college recruiting space and doing very well. So I was personally excited about hiring tools and got quickly interested in Laura’s vision to make the recruiting and hiring process become more fair and inclusive and help companies understand why they're having such a hard time building diverse workforces.

Is there any piece of advice that you would give founders who are up and coming next generation founders that you don't think get shared enough currently? Something that people are failing to focus on when they're thinking, “I want to become a founder”? Is there some aspect you see time and time again they forget and you would caution them to focus on?

Try and get as much perspective as possible. When I was an entrepreneur raising money, I felt that I knew and loved my team and my business, and I could pitch them all day long. But when I went into VC meetings, I was new at it and had never heard any other pitches. On the flip side, those investors had heard tons of them, yet I had no idea how I stacked up. I've definitely seen founders come through True who think they nailed it but they didn't. And I’ve seen founders completely hit it out of the park with us and were like, “Was that OK? I have no idea!”

My advice is to connect with other founders and see other pitches, or at least get some information on how high the bar is. I think that's how you get better. Don't try just work on your own idea, on your own pitch within your own bubble, but really try and see what else is going on out there, who's doing really well and connecting. How are they doing it? What's the subject matter?

A lot of what you're describing was actually the impetus behind why Alchemist got started. The founder, Ravi, felt the same thing, a lot of startups didn't really know how to compare and weren't really swapping notes and sharing. Alchemist has become like a community where you can share ideas, help each other out and that everyone is trying to get the best out of everyone else.

Exactly. The most worthwhile part of being a part of a program like that is learning from each other and getting perspective.

Then the last thing I'm really curious about is seeing how you get to see all the upcomings startups, tech products and services. What areas do you personally think are going to be the most exciting and you are most excited about in the upcoming near future?

I get that question a lot and actually I don’t know. Literally someone will walk through the door tomorrow with an incredibly exciting idea that we couldn't anticipate. All the super interesting things we have gotten really excited about are little bit out of left field. We're trying to be truly open to new people and ideas because our next great investment can come from anywhere.

About the Alchemist Accelerator

Alchemist is a venture-backed initiative focused on accelerating the development of seed-stage ventures that monetize from enterprises (not consumers). The accelerator’s primary screening criteria is on teams, with primacy placed on having distinctive technical co-founders. We give companies around $36K, and run them through a structured 6-month program heavily focused on sales, customer development, and fundraising. Our backers include many of the top corporate and VC funds in the Valley—including Khosla Ventures, DFJ, Cisco, and Salesforce, among others. CB Insights has rated Alchemist the top program based on median funding rates of its grads (YC was #2), and Alchemist is perennially in the top of various Accelerator rankings. The accelerator seeds around 75 enterprise-monetizing ventures / year. Learn more about applying today.

An Interview with Laura Gomez, CEO, Atipica

Her family immigrated to America when she was eight years old and settled in the Silicon Valley area. Shortly afterwards, she got an internship with Hewlett Packard. No one at her internship looked like her, and she hated it; it made her want to stray away from tech. However, her parents — who’d come to the U.S. to make a better life for her children — saw that tech would be an incredible opportunity and pushed her daughter to continue. Determined not to let the industry make her into a victim, she decided she’d work in tech, “whether the industry embraced her or not.” She believes she made the right choice going forward with tech; now, years later, diversity is dominating the conversation in the industry. Since then, she’s worked at huge companies like Twitter and YouTube, helping them translate and localize their applications for a global audience. Her latest endeavor, Atipica, helps tech companies find and hire diverse candidates; says she’d rather fail trying to solve the problem of diversity in tech than to never tackle it. Laura has raised $2M in seed funding led by True Ventures.

In order to get a more in depth look into Atipica and the mind that created it, we conducted an exclusive one-on-one interview with the company’s founder Laura Gomez. We pushed for answers to questions that people often want to ask Silicon Valley’s next-gen entrepreneurs, but seldom have the chance. By the end of this snapshot, we hope you have a sense of this amazing founder’s story and a few lessons to take away for yourself.

What exactly is your startup bringing to the marketplace?

What we bring to clients, investors and or our own team members is thinking of AI in HR in a more thoughtful and inclusive lens, powered by data and machine learning in the workforce. While there are many tools out there for HR, we are the only ones thinking of it as a holistic, inclusive solution and building it with a diverse team.

What was the impetus behind creating your startup?

The conference I just came from was actually MC’d by a former human resources business partner at Twitter. While technically I do not have any direct HR experience, I have worked very closely with HR throughout my career. Regarding the starting idea, it began with me thinking of a thoughtful and inclusive way that we can better understand diversity at the top of the funnel so that we can apply what happens to diverse employees and what doesn’t, and try to move away from anecdotal approaches to diversity and inclusion.

What is the most challenging matter you as a startup are currently facing?

I think the biggest hurdle is people not only picturing Atipica as a solution for social impact and diversity, but seeing it as a business intelligence tool that is adaptive to the dynamics of the workforce, which includes different genders, races, ages, and other kinds of diversity. The challenge is understanding the market outside and how to position ourselves, and getting people to not just thinking it’s a social impact and diversity solution, but rather that it’s a business intelligence technology that’s helping businesses adapt to what the workforce looks like now and what the workforce will look like in 5 or 10 years.

Can you tell us a little about your background before you started your startup?

I’ve been in tech since I was seventeen. I had my first internship at Hewlett-Packard, and since then went and studied in college. I didn’t really focus on computer science because I felt a lot of the imposter syndrome. After college, I joined a lot of early stage tech companies all at various stages of growth. While working at them I saw a need for more diversity.

What previous experience or situation do you feel best equipped you for your current role?

Growing up I always had a hard time assessing myself and my skills, but I also loved languages and loved reading about and interacting with new technologies. It wasn’t until I was in my late twenties that I realized that there was a natural intersection between the two, called localization. As I continued with my interests, I realized that technology could help me assess career paths and even help companies better understand the skillsets of people. That is something I want to incorporate into Atipica as well. How are people assessing themselves, how are they intersecting their skill sets with their own mindset and passion in the long run?

If you could go back to the first day of your startup, what advice would you give yourself?

Be patient with the fundraising process. Patience in understanding the complexity of what it takes to get funding is fundamental to becoming a founder. While people do usually want to be patient and not force it, the process requires a thorough understanding. It’s really not just the waiting that’s difficult, but you need to have patience in understanding the process.

What made you apply to Alchemist? Why not others?

A former coworker from Twitter is an Alchemist alum so I decided to consider it. I started researching, and I found Alchemist was considered the best accelerator. I then reached out to a friend who knew Ravi so that they could introduce me to him. The rest is history. Since joining Alchemist I actually made one of my closest friends by going through the program. She’s also an Alum. I saw the success of Alchemist, the prestige, the thoughtfulness of the program that Ravi had built and it made me think: “This is where I want to be.”

What was the most valuable thing you took from being a part of Alchemist?

Learning how to sell to enterprises. My whole career, I had only ever sold to consumers. I think the enterprise component allowed me to better understand all the components that make up enterprises in general. Obviously there’s an emphasis on revenue, but there’s also an emphasis on positioning and on the value to the client. Being better able to see through the lens of enterprises and how they look at startups was very helpful.

Can you talk about a time in which you thought all hope was lost and how you made it through that?

It happens to founders, if not every day, at least once a week or every month. This month alone it has happened to me twice. The main one had to do with someone that I thought was going to lead my round of funding, but it just got to a point where it just didn’t seem like it was going to work out. They had their own concerns about the business, and I had my own concerns about aligning myself with their values. I think it was one of those things that should have been addressed and discussed earlier on, but those are the types of things that happen, and I learned from it and have moved on.

I personally am a big fan of acknowledging the things that I can’t control and then focusing on the things within my control, plus by doing that it helps me not go into a rabbit hole of “oh my gosh I can’t believe this happened” or “poor me” victimization. Since I’ve started focusing on that, people have noticed how much happier I am. I feel more in control of my life and my startup. Always make sure to be grateful for everything. Even for example if you meet with an investor and they decide not to invest, thank them and walk away with gratitude that they were willing to meet with you and that you were able to learn from that. Being grateful in life opens so many doors and will never hurt you.

What entrepreneurial lesson or skill took you the longest to learn or are you still learning?

All entrepreneurs, whether they know it or not, are going to face some sort of ethical dilemma. It might be who they take money from, what they’re building, who is it going to affect. I have had to learn how to handle those dilemmas and to stay true to who I am. This skill is especially important right now when we have big tech companies being held accountable for various intrusions of the democratic processes or how they’re building their product and their businesses. Practicing ethics and integrity is something that I continue to learn each and every day.

Do you have any advice for female or minority founders?

Yeah, definitely! I actually just met with a female venture capitalist this week to see if she had ever led a preemptive Series A round. I asked because I really wanted to know if it was true or if it was just my own bias, but I had never heard of a woman or a person of color that has been a part of a preemptive Series A round. That being said, I know many male founders that have recently closed preemptive rounds just by talking to an investor. I think we need to acknowledge the systematic discrimination — men can get a $10M term sheet from a coffee, but not female or underrepresented founders. How I stay balanced is knowing that I can only control my own company and my own strategy when it comes to fundraising and not any external factors like who’s getting funded and are they preemptive or not. However, if there is a trend where minority founders aren’t being treated fairly, you have to acknowledge it and hold the industry accountable.

Has there been someone that has helped you along and that you don’t think you’d be here if it wasn’t for them? How did they do it? How did you find them? How did you build that relationship?

Yes, it is a VC friend of mine named Freada. She was one of the first people I ever pitched to. When I pitched to her it was horrible. I wish I had recorded it because it was absolutely terrible. But all of the partners and associates actually gave me really great feedback. I met with her afterwards, and she told me to focus on what I really wanted to make and then to build that well and find people who are willing to buy it and then come back to them. I took her advice and seven months later met my lead investor through her. And her firm, Kapor Capital, became an investor as well. So I definitely wouldn’t be here without Freada.

Did you already know her or how did you meet her?

I didn’t know her. I actually just randomly reached out to one of the principals, who is now one of my closest friends, there at the VC firm that I kind of knew of. I reached out and I said “Hey do you have time for coffee?”, and she said yes, but asked me if I’d rather meet with her coworker Freada because she was really passionate about what I was trying to start. She eventually became my mentor and colleague and investor. As a founder, you need to be willing to just put yourself out there and ask to meet people.

What constitutes success for your startup in the next 12 months?

I want to build a company based on values, integrity, using AI and machine learning to coach people rather than trying to automate and replace people and their skill set. I want the world to know that not all tech companies are trying to replace people and that not all artificial intelligence is biased; and I really want them to know that there’s a company out there thinking of thoughtful and conducive ways to use this technology to help the current workforce.

What constitutes success for you personally?

Success for me is having a proud legacy to leave behind. No matter what happens, I have met amazing people who really believe in me and my mission. At the end of the day I’ve done great work and built something I really believe in and am proud of. I have two nieces and if they ever read about me and what I’ve done, I know they’ll be proud.

Are there any insights you have learned that you want to share with the next generation of entrepreneurs?

I would tell them to stay true to their convictions. Whatever you’re building, make sure to find a support system. Don’t think it’s a weakness or a sign of desperation to ask people for help. Make sure to ask people for support, ask for advice, ask for opportunities. I believe that most people out there are good people and are willing to help, and if they’re too busy and aren’t willing to help, then you shouldn’t take it personally. Don’t be afraid of rejections, but rather be thankful for each and every opportunity that you’ve been given, and that will make a big difference.

About the Alchemist Accelerator

Alchemist is a venture-backed initiative focused on accelerating the development of seed-stage ventures that monetize from enterprises (not consumers). The accelerator’s primary screening criteria is on teams, with primacy placed on having distinctive technical co-founders. We give companies around $36K, and run them through a structured 6-month program heavily focused on sales, customer development, and fundraising. Our backers include many of the top corporate and VC funds in the Valley — including Khosla Ventures, DFJ, Cisco, and Salesforce, among others. CB Insights has rated Alchemist the top program based on median funding rates of its grads (YC was #2), and Alchemist is perennially in the top of various Accelerator rankings. The accelerator seeds around 75 enterprise-monetizing ventures / year. Learn more about applying today.

Checklist for Running Your First Board Meeting

A first board meeting is a big and life changing milestone. As founders, you survived weeks of due diligence, followed by a term sheet and then a wire of a few million dollars. Now it is time to be a CEO and experience and run your first board meeting with the investor or investors who sit on your board and blessed the deal.

It can be overwhelming. Here are a few coaching tips, based on my experience as a board member, to help first time CEOs be prepared and maximize the limited time you have with your board.

Checklist For Your First Board Meeting:

  • Get On Calendars: Executives’ calendars fill up months in advance. Remember that you are asking for 3 hours of a partner’s time, several times a year. In some cases, investors will have to fly in for the meeting. As a best practice, ask one of your board members’ administrative staff to own responsibility for scheduling the meetings.

  • Pick the Best Dates: The board meeting should take place after the quarter ends. This gives your finance and sales team enough time to close the quarter, giving the complete picture of sales data. Your cash runway is a key metric. Missing one deal could have a big impact. Having board meetings after the end of the quarter ensures you have the actual bookings number. (Note: most boards also have standing calls during the quarter.)

  • Share Decks: Email your board decks at least 72 hours in advance. This will help the board be prepared to ask meaningful questions and give feedback. Board members might also request that you pull additional information for the meeting. Emailing decks ahead of time gives you and your leadership team a few extra days to meet any such requests.

  • Use the Preferred Template: Ask the lead investor if they have a template that they would like you to follow. Chances are they sit on multiple boards and have a preference how they like to review the data. Once you have the template, share it with your leadership team. Have them fill out their section. For example, Sales, Finance, Product, Operations will each have their own slide or slides. Each section should start with a high-level overview of the insights and learnings of the quarter.

  • Prioritize Board Discussion: Always have two or three meaningful topics that you want to discuss with the board. Interact with the board as you prepare your slides. They are a sounding board for what you want to cover. Remember they have done this before and can only help when they know what problems you are trying to solve.

  • Leave Time for Governance: At the end of each board meeting, you will do the housekeeping: approve stock grants, minutes and other items that the board needs to vote on. Always have the most current cap table handy. That gives the board perspective on the impact on the employee option pool as they approve grants.

  • Hold a Dress Rehearsal: 24 hours before your board meeting, meet with your leadership team and do a dress rehearsal. It is important that everyone is on the same page. This might be the first board meeting for them as well.

  • Take a Breath: Congratulations on making it this far! Give yourself and your team the credit you deserve for the huge milestones of a Series A raise and first board meeting. There’s a vast amount of work ahead, but this is an achievement to celebrate.

About Darren Kaplan

Darren Kaplan is the co-founder and founding CEO of hiQ Labs (, a data science company, informed by public data sources, applied to human capital to make work better. Mr. Kaplan is an Alchemist Accelerator mentor, working with Augmented Reality, Cyber Security, and HR enterprise SaaS startups.

About the Alchemist Accelerator

Alchemist is a venture-backed initiative focused on accelerating the development of seed-stage ventures that monetize from enterprises (not consumers). The accelerator’s primary screening criteria is on teams, with primacy placed on having distinctive technical co-founders. We give companies around $36K, and run them through a structured 6-month program heavily focused on sales, customer development, and fundraising. Our backers include many of the top corporate and VC funds in the Valley—including Khosla Ventures, DFJ, Cisco, and Salesforce, among others. CB Insights has rated Alchemist the top program based on median funding rates of its grads (YC was #2), and Alchemist is perennially in the top of various Accelerator rankings. The accelerator seeds around 75 enterprise-monetizing ventures / year. Learn more about applying today.

Using Design to Inspire Disruptive Thinking

Image result for design principles

Emotion factors into customer experience, and as a result, into purchasing decisions. A customer’s experience isn’t just about features, it also includes how the product or experience makes them feel. It’s the moments of delight a customer encounters, and also the overall feeling they take away after interacting with your product.

Great customer experience is why travelers opted for Virgin America when United and American Airlines offered more flights per day. The Virgin experience, and the brand’s unique personality was ultimately more appealing than other airlines’ “feature” set

Investing in design to create an experience, rather than just a product and feature set, can be a key element of a company’s success.

Design is empathetic

Design can be seen as abstract concept. Robert Brummer, industrial designer and founder of SF-based design studio Ammunition has said: “Everyone is a designer.” What he means is that all of the people involved in bringing a product to life (the engineer, the manufacturer, the product manager...) need to be bought in to the design vision since they’re executing on different parts of this shared strategy.

Empathy is critical for design success. When you understand the context of a product's use (and how the person using it feels), you make really important discoveries. Understanding your users doesn’t just mean interviewing them––observation can be even more revealing. Observations uncover insights that interviews may not because users will often tell you how a process is supposed to work, rather than show you how it actually works.

To ensure that every decision reflects the best user experience, startups can keep these key principles in mind:

Five Key Principles

  1. Make it simple – Find a way to make someone's life easier, and maintain your focus there. It takes discipline to keep things simple, but focusing on doing one key thing really well could be a differentiator.

  2. Inspire delight – Create efficiency around a pain point. Help users complete something in an engaging and compelling way.  

  3. Exhibit craftsmanship – Pay attention to details. Think about going to a Disney resort:you instantly become part of a crafted, well-orchestrated experience.

  4. Deliver unique value – Avoid getting trapped in incremental improvement. Be sure you're focused on doing something unique and different. The NEST thermostat is a great reminder that there are opportunities for  breakthrough innovation even for everyday household objects.

  5. Focus on human goals – Understand your customer's world. Take time to understand who your users are.Don't trust internal opinions only because your perspective may not reflect the greater population.

A design-focused process

Design-driven companies use collaborative teams to get to disruptive ideas faster. Product management, product marketing, and design  should work together from day one. Here’s an outline of a development process that puts your users first:

  • Discovery – Focus on your customer development work to uncover your users’ needs first.

  • Conceptual design – Use the data you discovered to ideate upon possibilities.

  • Detailed design – Narrow your scope. Sketching, wireframing and prototyping, and then sharing these prototypes can help you get specific and disrupt assumptions.

  • Implementation – Discuss tradeoffs and ensure that with every change you’re not compromising the overall experience.

  • Post ship – Go back and talk to your users again. You may find new opportunities for the next version.

Find the right people

For small companies unaccustomed to hiring designers (and other user experience professionals like researchers, prototypers, or writers), finding the right people can be challenging. Design is an iterative process, so whomever you hire should be willing and able to work with you through a development process, listen to feedback, and make changes.

Communication is key. Your designer should be able to answer questions about why they made certain decisions, communicate to you why the overall design proposal works, and, as noted before, take constructive feedback. There’s lots of talented new grads and contractors who’d be motivated to work with startups and small companies. Working with a company where design is a priority at the earliest stages of growth should be an attractive prospect for designers. The benefits gained from designing an overall customer experience should prove invaluable to your business.

About Catherine Courage

Catherine serves as Vice President of Ads & Commerce User Experience at Google Inc. She was previously SVP of Customer Experience at Citrix Systems, Inc. where she led the company-wide customer experience initiative with responsibilities covering brand, social, web, product design, information experience and business process reinvention all to drive adoption and loyalty among customers, partners, and employees. She also served as SVP of Customer Experience of DocuSign, Inc. and the Founding Member of the experience team at She has twice been recognized by Silicon Valley Business Journal as one of 2011's 40 under 40 and 2013's Women of Influence. Ms. Courage holds a Masters of Applied Sciences, specializing in Human Factors, from the University of Toronto and Bachelor of Science from Memorial University of Newfoundland.

About the Alchemist Accelerator

Alchemist is a venture-backed initiative focused on accelerating the development of seed-stage ventures that monetize from enterprises (not consumers). The accelerator’s primary screening criteria is on teams, with primacy placed on having distinctive technical co-founders. We give companies around $36K, and run them through a structured 6-month program heavily focused on sales, customer development, and fundraising. Our backers include many of the top corporate and VC funds in the Valley—including Khosla Ventures, DFJ, Cisco, and Salesforce, among others. CB Insights has rated Alchemist the top program based on median funding rates of its grads (YC was #2), and Alchemist is perennially in the top of various Accelerator rankings. The accelerator seeds around 75 enterprise-monetizing ventures/year. Learn more about applying today.