8 ways our community is fighting COVID-19

As the world works to contain the COVID-19 outbreak, our own community has gone into overdrive. We’re so proud of our Operator Collective LPs for leading this charge. Here are some of the ways they’re using their platforms, tools, and networks to help. 

  • Eric Yuan, Kelly Steckelberg, Janine Pelosi Zoom
    In today’s everything-from-home economy, Zoom has become the de facto tool for communications, virtual meetings, remote work, family chats, and more. But what about our schools? As educational institutions shut down around the world, the Zoom team truly stepped up, offering its video conferencing tool free to any K-12 school.

  • Rachel Carlson Guild Education
    Rachel Carlson has emerged as a persuasive voice in the coronavirus crisis, imploring her fellow business leaders to #StopTheSpread. She co-wrote a letter imploring Americans to take “bold action” to slow the spread of the coronavirus, and then a more direct ask to corporate leaders. By circulating the letter, Carlson hopes business leaders can remove some of the burden from local, state, and federal governments.

  • Kimber Lockhart One Medical
    One Medical is a membership-based primary care practice. In addition to offering same-day appointments, providers offer 24/7 video visits. One Medical has also created a Coronavirus Help Center with resources to help everyone stay up to date with the latest information.

  • Nihal Mehta – Eniac Ventures + Reshma Saujani – Girls Who Code
    Nihal Mehta recently launched Help Main Street, a crowdfunded platform to keep shops, restaurants, and industry workers afloat via gift card sales. Want to help your local favorites? Go to helpmainstreet.com to purchase gift cards to provide critical cash support during the COVID-19 outbreak.

  • Jennifer Tejada – PagerDuty
    PagerDuty is a platform that helps companies manage the full spectrum of their digital operations. As healthcare organizations struggle with demand and stress, they need to stay prepared and “always on.” To that end, Tejada and PagerDuty recently announced an offer for healthcare organizations: 20 PagerDuty licenses free for six months.

  • Christina Kosmowski Slack
    Slack has seen huge increases in paid customers since the coronavirus outbreak, offering plenty of content to facilitate remote working (including this Guide to Working Remotely in Slack). They’ve also announced free upgrades to teams working to solve the crisis.

  • Michelle Zatlyn – Cloudflare
    Cloudflare accelerates Internet properties, helping businesses stay productive from any location. Early in the coronavirus outbreak, Zatlyn and team made their enterprise-grade features available to small businesses at no cost, offering unlimited seats of Cloudflare for Teams through September 1.

  • Lexi Reese – Gusto
    Gusto is an automated platform for payroll, HR, and employee benefits, aimed specifically at small businesses. They’ve recently launched a COVID-19 Resource Hub to offer small businesses the most updated news, information, and advice.
We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

It’s uncomplicated: Why we’re crazy about DataGrail

The company: DataGrail 

DataGrail is a privacy platform that simplifies compliance with GDPR, CCPA, and similar privacy regulations. In this Age of Privacy, DataGrail is helping companies stay in line with regulators while building trust with their customers by driving new standards of transparency and accountability. 

DataGrail was built on the principles of diversity and inclusion from the very beginning. About 40% of the company is female (a percentage which has never been below 30%), 50% of the board members are female, and 11% of employees identify as LGBT+ or gender non-binary. Read more about DataGrail’s commitment to supporting workplace diversity in their recent blog post.

Why you should pay attention 

The rapid-fire expansion in privacy regulations combined with the dramatic explosion in data collection is creating major turbulence for businesses. The average enterprise has 88 different systems that could contain personal data, and Gartner predicts that by 2023, 63% of the planet’s population will have GDPR-like personal data protection (up from 10% today). Yet DataGrail’s recent consumer survey shows 83% of Americans expect to have control of how businesses manage their data. Companies clearly need help navigating this landscape, and DataGrail is leading the way.

The details 

The issue is clear: privacy is a fundamental human right and essential to democracy. So in 2018, Daniel Barber, Earl Hathaway, and Ignacio Zendejas launched a business built on this covenant of trust. With 200+ pre-built connectors, the DataGrail Privacy Platform gives a 360-degree, real-time view of the applications a business uses, then maps personal data associated with each of those systems. Customers can manage their privacy request workflows and email preferences across applications.

Building trust through transparency. Taking complicated out of compliance. DataGrail is changing the game.  

How it works

At the core of the solution is DataGrail’s Live Data Map, which provides a continually refreshed blueprint of where data lives in the organization. Any changes made to the systems are reflected automatically. Privacy requests are streamlined, eliminating human errors and reducing risk. And DataGrail’s hundreds of pre-built integrations (Salesforce, Adobe, Oracle, AWS, and more) streamline the onboarding process, making data discovery almost instantaneous. This makes sure companies not only achieve compliance, but are continuously compliant over time as regulations change externally, and business systems, fields, and owners change internally.

Why were obsessed 

Today trust is a currency, and DataGrail is here to help companies grow and manage this business-critical resource. DataGrail clients like Overstock.com, Restoration Hardware, Revolve, Databricks, and more rave about how the company helps them manage data privacy risk and compliance (simplicity, automation, and real-time insights are the common refrains). By taking on the complexity of the continually shifting regulatory landscape, DataGrail is simplifying compliance and helping its clients stay ahead of the curve. 

Get involved

Ready to supercharge your company’s privacy disciplines? Let DataGrail handle your compliance needs. Get started here now. 

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

Steady on: Downturn advice from a seasoned investor

There’s an old English political saying that says the Conservative Party never panics, except in crisis. That feels especially true these days. Perhaps you’ve never really experienced an economic downturn, but I’ve been through at least two: In 2000 (when I was in the eye of the storm at Cisco) and again in 2008 (when the crisis hit hardest outside the tech world). Each brought with it a set of lessons that I’m happy to share as we navigate this latest challenge. 

1) Turn off financial media.

At this point, the story is the market decline, which the financial media will cover in all its gory detail. Just as financial media over-rotates to bullish commentators during good times, they will over-rotate to the bearish folks now. At some point in the cycle, we’ll see folks predicting the end of capitalism and democracy… But we have withstood greater challenges than this. Warren Buffett, who in many ways is the sage of market downturns, has a wonderful saying: Be fearful when others are greedy, and be greedy when others are fearful.

2) The cloud is still the greatest opportunity for tech investors. 

For those of us in tech, I believe the big thesis on the move to cloud not only does not change, but actually may accelerate. We’d been in a magic period where both existing companies and startups were ready to adopt new technology at a breakneck pace. Tech companies will need to wait and see if startups are still spending, but I believe enterprises will continue to spend. The new world is much cheaper than the old one, and folks may need to be aggressive in fixing old cost structures.

3) This is a great time to have dry powder. 

We’re still early in the economic downturn (where VC Twitter proclaims boldness in the face of risk). That’s going to change. Soon we’ll find out which companies have been overspending, and which VCs are willing to bet that those companies can improve. My personal feeling is that bad and even mediocre business models will feel a lot of pain.

The flip side is that funds like Operator Collective (which has a clear majority of its funds unspent) will have opportunities to invest in great companies at excellent valuations. Unlike most other VCs, Mallun Yen and Leyla Seka do not have a large legacy portfolio to triage, and instead have the chance to wait, watch, and act as valuations decline and markets become clearer. Rather than compete in overpriced rounds, Operator Collective will have the time and resources to cherry pick the best opportunities. 

4) Cash is still king. 

If you’re operating a company, that particular golden rule still applies today: Do not run out of money. Be ruthless in analyzing your cost structure. If you can adjust your business model to have your cash last longer, you have a greater chance of being able to raise again when the market comes back. The faster you adjust to this new reality and the faster you take cautionary action, the better prepared you are for the inevitable recovery. 

Separating fact from fiction 

In up markets, every VC looks like a genius – but markets like these let us know who’s the real deal. I hope all of you remain upbeat and look for the opportunities that will certainly be there in and amongst the damage. Steady on, friends. 

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

15 tried-and-true tips for working from home

The coronavirus outbreak has highlighted our need for flexible work structures, with many organizations mandating remote work this month. Certainly distributed teams and satellite offices have grown in popularity in recent years, thanks to the wonders of high-speed Internet, cloud applications, and fancy collaboration tools, but it’s been something of a learning experience for this surprise new WFH-force.

Perhaps you’re still in the honeymoon phase, that blissful period when you realize you no longer have to wear pants with zippers, but the psychological aspects of remote work may set in before long. We’re here to help. Our Operator Collective team is fully distributed – from New York to Berkeley, Vancouver to Houston – so we’ve had to figure out what works for us. Here are our top tips for getting into that remote work groove. We’d love to hear your tips for working from home, too – Please share them at @OperatorCollect.

Mallun Yen, Founder and Partner

  • It can be easy to forego exercise. Two mornings a week, we block out time for exercise and don’t schedule meetings until 9:45. But don’t cheat – Sign up for classes in advance to keep yourself accountable.
  • Keep your video on when you Zoom into meetings (try these tips). It keeps everyone on task and connected. 
  • Look to the pros. Zapier, a pioneer in distributed teams, has been sharing tips for a while.

Leyla SekaPartner

  • Make your desk area beautiful. I cover mine in flowers and things that make me happy.
  • Get moving! I try to walk 10K steps around my house before noon. I may look crazy yapping on the phone as I circle the house like a shark, but it keeps me sane.
  • Do something for you. My friend April suggests growing a vegetable garden. I dress my cat up in costumes (a lot), but you could try learning a language or making every recipe in a cookbook. 

Ambrosia Vertesi, Operating Partner

  • Reserve the first five minutes of a virtual meeting for watercooler talk. At Duo, Dug Song would start meetings by sharing appreciations which helped build connectedness.
  • Play Team Chatroulette to connect with people outside your immediate orbit.
  • If you don’t schedule snack breaks and bathroom breaks, nobody will. 

Ruthie Miller, Head of Marketing

  • Create a basic schedule and stick to it. Resist the urge to sleep til noon.
  • Don’t work from your bed. As tempting as it is, that’s a slippery slope.
  • Use your regular commute time to do something for yourself – read, send a card, get an #OfficeDog.

Marley Sarles, Events and Operations

  • Don’t forgo team building. Use Zoom for a team coffee, happy hour, or remote dance party.
  • Throw in a load of laundry between meetings. You can be so productive at home!
  • If you don’t have a lot of calls, switch things up by working at a coffee shop or restaurant.

Your turn! Please share your tips for working from home with us at @OperatorCollect.   

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at our website or by connecting with us on Twitter and LinkedIn.

Growing up on HBO: The early feminist movies that inspired me

For several years now Hollywood has been engulfed in a trend of remakes, redoing the old movies we loved in our youth in hopes of giving them new life as modern-day classics for a new generation. Most of these remakes have fallen flat for me, but I have to admit I was pretty excited about the new Top Gun

My husband and I decided we should show our kids the original movie so they can see its greatness for themselves and note the differences. Old versus new fight scenes! Bigger, badder explosions! More beach volleyball! We knew they’d love the both versions.

Top Gun movie imageBut 20 minutes into the classic, my 12-year-old turns to me and says, “Mom, I can’t believe you like this. These guys are sexist jerks. This movie is awful.” I was totally caught off-guard. Yet as I continued watching, his point became painfully obvious: inflated male egos everywhere, a cocky student hitting on his female teacher, testosterone to the max. Afterward, my 9-year-old commented: “The only good part was the end when they finally started blowing things up.” 

How did I ever think this movie was great? As I thought more about it, I began to realize that Top Gun is a classic snapshot in time. It was, unfortunately, where we were as a culture in 1986. I loved Top Gun back then (and still love The Hunt for Red October now), but the basic message I got was that the men were out there doing things and in charge… and the women weren’t. 

My parents are foreigners; my Dad left early every morning and came home late, while my Mom worked to keep the home running smoothly. From my own house to the Brady Bunch, I saw the way the gender roles stacked up. Fortunately one day my parents invested in a new invention – The Home Box Office – and that’s where I connected with some key movies that helped me find my place in the world. So in honor of Women’s History Month, I’d like to share a few of the feminist movies that defined me.

Women dominating the working world  

9-5 movie imageThe number of working women has steadily increased since WWII, but there was a seismic shift in the 80’s with movies that portrayed women as taking control, rising through the ranks, or becoming entrepreneurs. 9-5, for example, tells of a gaggle of secretaries who scheme to transform their office into an inclusive workplace that offers flexible hours, equal pay, and onsite daycare. In 1980! Companies still struggle with those things today! 

And then there’s Baby Boom. Should women have to choose between having a kid and having a job? Not Diane Keaton and not me. Melanie Griffith was Working Girl, which postulates that just because someone starts out answering phones, doesn’t mean she’s going to end up answering phones. And finally, Selena, the biographical story of the Tejano mogul who sang, danced, and toured her way to a clothing line and cult following. 

Women breaking cultural archetypes 

Princess Leia imageThe movies of my youth also started to break the archetype of the frail, incapable woman. First there’s Private Benjamin, which shows Goldie Hawn join the Army on a whim and discover the value of inner strength. The lesson? The life set before us is not the one we have to lead; we are tougher than we think we are. And then there’s She-Devil, which portrays women not as helpless victims, but as clever and resourceful opponents. Perhaps a Vesta Rose is what the technology industry needs right now. And my absolute favorite, Star Wars, which created the ultimate feminist idol, the woman who took absolutely no sh*t and ruled the galaxy: Princess Leia.

Behold the power of female friendships

Waiting to Exhale imageOf course, there were plenty of feminist movies that depicted the power of friendships among women, like Waiting to Exhale, which shows how women watching out for each helps them build power. We all need those trusting relationships in our lives.

At the time, grief was still a matter largely kept private, but thank goodness for two classics – Steel Magnolias and Beaches – who opened us up to emotion. Those movies highlight just how much we need to rely on our friends when the going gets tough. Truly they both are tearjerkers that present the comic with the tragic in a beautiful way.

Inspiring a new generation of women

These old storylines, which were totally outnumbered by slapstick comedies and male heroes, came at just the right time to launch a new generation of feminism. We began to see what was possible, what could happen when women take charge. As a result, the women who watched those movies are now pushing for equal pay in Hollywood, amplifying the #MeToo movement, and working for greater diversity and more representation

They’re also bringing women into venture capital, helping women invest, leading companies, starting companies, and running for office in record numbers. And now that we have models for what these roles actually look like – on the big screen and in our very own world – the girls of today will know what’s possible. There is no limit to what we can do.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

Operator spotlight: DEI leader Aubrey Blanche

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas. This month we spoke to Aubrey Blanche, a leader in the Diversity, Equity, & Inclusion (DEI) space and newly announced Global Head of Equitable Design & Impact at Culture Amp.  

It seems like every company is trying to build diverse, inclusive teams – yet entire industries are still quite homogeneous. Why is this such a challenge?

AUBREY: Companies are incredible at saying they care about building balanced teams and inclusive cultures, but when it gets down to it, most are unwilling to support the work that would help achieve that outcome. Sure, PR and recruiting efforts can offer a short-term boost in numbers, but they don’t address the fundamental problems causing the lack of representation in the first place.

Companies that are truly dedicated to creating change will ask questions like:

  • How is bias built into our hiring and evaluation systems and how can we redesign these systems to be more accountable?
  • Are we spending more budget on swag than we’ve allocated to DEI?
  • What resources are we providing underrepresented people to build community and provide feedback on what’s not working in our culture? 
  • What are the consequences when individuals or leaders don’t live up to our behavior standards or goals for advancing representation and belonging?

The companies I’ve seen move forward the most are those whose executives have the humility to take responsibility for missing the mark in the past + take ownership of building a future in line with the promises they’ve made to employees. 

What’s one piece of advice you’d offer a company looking to improve its hiring process? 

AUBREY: Stop using candidates’ educational institutions as a signal on whether or not they’ll be wonderful teammates. The number one factor that determines whether someone went to a “top” university is the amount of money their parents made. That’s not a skill – it’s a (fortunate) accident of birth – and it lowers the overall quality of your talent pool. 

Give us your hot take on the future of DEI in America. 

AUBREY: I think we’re going to have to rely a lot more on companies to make changes, because our governmental systems aren’t incentivizing changes in the ways we’d like. Since industry often moves faster than government, I think there’s incredible potential. The three things I want to become standard:

  • Corporate courage to fire harassers and abusers instead of locking victims in forced arbitration and non-disclosures.
  • Shift of budget from marketing-focused activities to those that create equitable experiences internally (like funding for accessibility work and career pathing for underrepresented people). 
  • Expansion of the discussion to not only include gender and race, but also disability, neurodiversity, caregivers, and formerly incarcerated people, and others (including intersectional identities). 

What’s one thing any company can do to foster a sense of belonging? 

AUBREY: The best way for leaders to get the ball rolling is to begin soliciting feedback on what they’re doing that is or isn’t creating a sense of belonging for folks on their team. Once they have that, it’s imperative to share what they’ve heard back with the organization, commit to specific changes, and have a mechanism for updates and accountability. And they should repeat this exercise quarterly. This is work of continuous progress: there’s always more to learn and ways to improve.

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

AUBREY: I worked part-time at Talbot’s for 7 years, starting at age 14. I was so proud to have my own income! It mostly involved folding clothes, counting inventory, and staying patient when people were having meltdowns about cashmere. People often talk about that kind of work like it’s easy, but I can’t imagine anyone who’s done it thinking that. It requires persuasion and emotional intelligence, and it’s also physically taxing. 

What’s something operators don’t often worry about but should?

AUBREY: Whether their social networks reflect the diversity they say they want in their workplaces. We all have a tendency towards homophily, but by building more diverse personal networks (business and social), we’re more likely to be more open and innovative, not to mention more adept at conducting ourselves in the workplace in ways that support people from all backgrounds. 

Whats one book that’s vital for everyone to read?

AUBREY: I am a huge bibliophile – Here’s what I got through in 2019, and an overview of some of my favorites. If there is one book I want all business leaders to read, it’s The Memo by Minda Harts. It’s a professional advice book for women of color that I think would benefit a lot of White folks in understanding how fundamentally different their experiences are, which is the first step to being more effective allies.

I’d also strong encourage folks to read How to Be an Inclusive Leader, Technically Wrong, Algorithms of Oppression, and Winners Take All to gain a better understanding of how the beliefs we hold and choices we make create fairness or inequity. 

What’s something at work that makes you roll your eyes every time?

AUBREY: “We don’t want to lower the bar” when talking about building a more balanced team. Let me be clear: if your team is not equitable and balanced, it is because of low or unfair standards. A balanced team is a result of holding yourself to the highest standards. 

What’s the one condiment you could never live without? 

AUBREY: Hot sauce. I have an entire shelf in my fridge just for my hot sauce collection, and have been known to leave a bottle at the homes of people I visit often who don’t enjoy it as much as I do.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

Why we’re obsessed with Guild Education

The company: Guild Education

Guild Education is a female-founded, Certified B corporation that’s on a mission to educate America’s workforce. Guild seeks to do well by doing good, offering a full-service platform that lets companies connect their employees to amazing education benefits.

Why you should pay attention 

Companies like Walmart, Disney, Discover, Lowe’s, and Chipotle have already realized jaw-dropping results with Guild’s end-to-end platform for education benefits and tuition assistance. (Disney reports record-breaking engagement with its Guild offering, while Chipotle reports 90% higher retention among employees who participate in the education benefits program. Whoa!) 

The details 

There are 88 million Americans who need upskilling or reskilling in order to compete in the future of work (64 million of whom haven’t completed college). Those were some of the facts compelling co-founders Rachel Carlson and Brittany Stich to shake up the traditional model and create a business for change. The resulting company, Guild Education, tackles the problem by helping Fortune 500 companies provide debt-free pathways to college for their employees. 

Why were obsessed 

Guild turns the traditional tuition reimbursement model on its head, reimagining a system that’s well meaning, yet antiquated and ineffective. To do this, Guild connects companies to a network of nonprofit, accredited universities and learning providers curated to provide the best outcomes for working adults. Their innovative tuition assistance model allows students to pursue associate’s, bachelor’s, and master’s degrees, as well as a wide variety of certificates and credentials without having to pay *any* upfront costs. (Students can also participate in English as a second language, high school completion programs, and college prep.) By removing that initial cost barrier, Guild’s model allows more employees to take advantage of the benefit + helps more employers realize a positive impact.

How it works

First the Guild team works with individual companies to build a customized education program and benefit policy that supports the company’s strategic goals, including objectives for recruitment, retention, and upskilling. Once the program is in place, Guild offers a team of coaches that works with individual employees to identify the right programs for them, then help with enrollment, coursework, and accountability. Completing the circle, Guild’s automated platform features dashboards and analytics to help companies track engagement, performance, retention, and overall results. 

Get involved

Ready to reimagine your company’s education benefits and increase employee retention, engagement, and success? Great idea – Get in touch with Guild Education now.  

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn

Everything you wanted to know about angel investing, but were afraid to ask

Thinking about angel investing? It’s a worthy way to spend your time and can be quite lucrative if you choose the right opportunities – but there’s also a great deal of risk. After my previous career in product at Salesforce and PayPal, I turned my technical experience into a sidegig as an advisor, where I reveled in helping driven founders and their teams succeed. Eventually I became an early stage investor, joined the launch of Backstage Capital, and recently joined the launch here at Operator Collective.

Now that I’m 5 years in, I feel equipped to share some knowledge, namely the answers that would have helped me as I started out. Here are the most common questions I get about angel investing (and special thanks to Courtney Broadus for sharing her considerable expertise and perspective here too!). Got a question I missed? Please reach out

What is angel investing? 

Angel investing is the term used when an individual investor gives money to startups or early stage companies in exchange for an equity ownership interest. This is often done using a SAFE note, which is a form of convertible note, that gives you the right to purchase or “convert” to equity partial ownership in the company at a future date and/or when other criteria are met. 

How is angel investing different from investing in a venture fund? 

Angel investing is done on an individual basis and requires considerable due diligence. Investing in a fund is putting your money in the hands of the fund managers, whose job it is to vet the companies and use their expertise and network to make sound decisions. Venture funds can be lower risk than direct angel investments, depending on stage, diversification, and sector; however, the whole category is high risk.

How do I get started with angel investing?

Start by choosing a focus. Operator Collective and many of our members focus primarily on enterprise b2b, but others prefer different areas – such as consumer, healthcare, edtech, or impact investing. As you think, determine what you’d like to learn about through the process + what area you’re passionate about (in addition to returns). 

Next, look for opportunities. Be intentional – Your network may not know you have expertise in scaling, hiring, or a particular technology. So let them know you’re looking to invest and the area in which you’d like to focus. Research the VCs in various spaces; then connect and find out who they’re investing in. Finally, offer yourself as an expert to startups to build a network. Use your knowledge of the industry, products and services, operations, hiring, and more. Always look for opportunities to develop your own career, network, and knowledge while you work with founders.

How do I set a budget for angel investing?  

Angel investing is a high-risk investment. Consider it money you may lose completely – and if you’re not ok with that, don’t do it. Once you’re willing to accept the risk, parcel out a piece from the high-risk portion of your portfolio. You may want to set a yearly spend or a total spend, or you might simply consider each investment individually to gauge your level of interest. Whichever direction you choose, think about the total loss you’re willing to accept and stay under it for at least the first few years. 

How much is a typical angel investment?

There’s such a broad range of angel investments that there’s really no typical amount. Investments can be in some instances as little as $5,000 at the low end and $250,000 at the high end, though $25k and $50k are more common. Amounts are negotiable, based on what you can offer in addition to money (like your subject-matter expertise or network).

What if I don’t have a lot of capital to deploy? 

Get involved in other ways! What skills do you have that might benefit a startup? You can ask for equity compensation for advising a startup, which is usually a fraction of 1% over a 18-24 month vesting term (0.10 is common, 0.50+ is often only given to someone with deep domain expertise and/or devotes a material amount of time, 1% is unusual but not unheard of). You can also use your network as your investment – Whom do you know that could help a startup? 

How do I manage risk?

If you’re risk averse or don’t have time to do full diligence, consider co-investing with a group; this gives you coverage in a broader range of areas. Peer validation of your investments also helps you make a more informed decision. Use deal diligence to mitigate risk; but understand that at the early stage there often isn’t a lot of information available about the company and its customers, since many are pre-revenue, pre-product. Evaluating the team and its ability to focus and execute is often the strongest indicator you have to go on (vs trying to learn everything about the particular business).

What do I get out of angel investing?

It takes 7-10 years for most funds and investment portfolios to move to final outcomes (called exits). Typical exits are:

  • Late stage buy-out: Modest gains of usually 1.5x-3x
  • Pro-rata and follow on: The opportunity to invest more money in the next round to maintain or increase your equity stake
  • Acquisitions and mergers: Company gets acquired or merges with another, which can range from barely a 1x return to 3-4x typical. Most common type of exit.
  • IPO: Usually the very highest return, 4-10x
  • Company folds: Often you lose 100% of your investment, but usually you can write 100% loss off in taxes

How can I increase the certainty of a solid angel investment? 

Again, this is a high-risk form of investing with no sure bets most startups fail. But if you want to increase your chances of success, you’ve got to put in a great deal of time. Find deals you like from founders you believe in. Vet the companies as heavily as you can. Once you’ve invested, don’t just walk away check in, help out, stay involved. 

How do I find companies to invest in? 

  • Use co-investing groups and VCs you trust to build a pipeline
  • Join an angel investing group
  • Look for startup programs like accelerators and incubators, which often host Demo Days and offer opportunities for mentoring and advising
  • Network at meetups, conferences, and events
  • Start posting content on your channels to showcase your expertise 
  • Follow online content like newsletters and social channels
  • Talk to current and former colleagues, alumni groups, friends, and neighbors 
  • NOTE: Cold-call type leads can be more time consuming and challenging to sort though, especially if there’s not a reasonable connection to the founders or their industry 

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

Operator spotlight: HR leader Cindy Robbins

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke to Cindy Robbins, a leader in the HR and Talent space.

You’ve been an HR leader for quite some time. What drew you to that career? What do you enjoy most about the People function? 

CINDY: It’s been a journey; I certainly didn’t start out saying I want to run HR one day. It was more of an evolution where I defined my path as I went along. I moved to San Francisco after college and started at a small consulting firm, where I learned several functions from recruiting to sales. I slowly realized I really enjoyed the talent function, which led me to a few different employers, including Excite@Home during the boom, Plumtree Software, and BEA. While at BEA, a friend introduced me to Erin Flynn, Salesforce’s head of global recruitment at the time. And once at Salesforce I was hooked. I loved being in a role where I could influence how to help employees feel valued. When I became President & Chief People Officer, I woke up every day glad for a role where I worked first and foremost for our employees.  

Why are people and culture so vital and defining for an organization? 

CINDY: Employees are redefining the rules of the workplace. If you’re an executive and don’t understand that, you’re in big trouble. Without a great culture, you don’t have an engaged workforce. And if your employees are not engaged and doing their best work, you will not make your customers successful. I remember the days when companies focused solely on the bottom line, but now employees want more. They want to be heard and want to be able to influence how the company’s values are defined and the actions behind them. 

It’s important to note that defining a culture happens over time. Think about something like workplace equality; no one was talking about that 10 years ago. So while it may not have been part of a company’s original DNA, it has to be there now. Values change, and every CEO, board member, and leader needs to listen, ask questions, and seek advice on how to adopt the right behaviors and values that drive the company culture forward over time. 

A lot of companies have been in the news recently for their negative cultures. How does an organization repair a negative culture? Is it even possible?

CINDY: I do think companies who run into negative culture experiences can turn it around. It takes leadership, trust, accountability, and transparency, and it has to start at the top with the CEO, leadership team, and board. Companies have to prioritize people and culture, and not just with nice words in a presentation. A culture is defined via actions and behavior. 

If you look at some of the companies with negative press, it’s important to note that it was often the employees who brought the issues to light – so it’s vital for every leader to LISTEN to all stakeholders and give them a safe environment to speak the truth. How do CEOs know what’s truly going on inside their companies? Not from just what they hear from the top of the ranks, but from the individual employees living it every day. How does the leadership team stay close to the truth, where messages aren’t cleansed as they rise up to the top? 

You’re known as one of the originators of the Equal Pay movement at Salesforce and beyond. How has that experience changed you + what are some lessons learned? 

CINDY: Leyla Seka and I both championed the Equal Pay movement at Salesforce. We did it because we were listening inside the company – listening to other women and to each other. Given that we were both in positions of power, we felt it was our responsibility to speak up. We knew we were taking a risk, especially when some were trying to tell us not to do it. 

I walked away with an awareness of what my role was – not just as the head of HR, but as a senior executive, a leader, a woman, and a Hispanic. I had influence, and I learned I could use it in positive ways. That’s important for every leader to know – You have to take risks to drive transformation. You can’t operate in silence. It’s doing good in the world that shapes who you really are.

And the other thing I learned was how much more powerful Leyla and I were together, two women just trying to make a difference for other women. We were proud of the outcome and the progress that was made, yet there is more work to do. I hope more companies, CEOs, and boards continue to highlight equal pay in their companies and provide the transparency needed around this critical topic.

What’s one amazing insight no one knows about HR?    

CINDY: HR is one of the hardest and least understood roles out there. HR organizations are often given the smallest budgets to work with, which is ironic given how important talent and people are to any company. It can be an organization that lives in constant frustration. But if you have a strong HR organization, you know it’s one built on trust – They are strategic thinkers and good listeners, show empathy when appropriate, and spread influence in a positive way. Many view HR as the police. I can’t speak for all HR orgs, but the ones I’ve worked with are full of genuine people who work tirelessly to make employees feel safe, engaged, and successful.

What’s the most epic way you’ve seen someone quit?

CINDY: Exits are not fun to watch. Ever. There are so many different types of exits within a company. Here’s one thing that always infuriates me: When an exit was caused because the employee had a bad manager. For example, when I would see exits because a manager never gave constructive feedback or had honest conversations, or when they prioritized company politics over doing the right thing. That makes made my blood boil.

What are some of the formative jobs you’ve had? Like AOC always talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

CINDY: In high school I worked in retail, which taught me about the customer experience, working your way up from the bottom, and how to work with peers. It also taught me about the value of not just doing my job effectively, but the various behaviors it took to get the job done right. I think a job where you start at the entry level point is good for everyone. It teaches you about value, humility, ambition, and working with others. 

What are some business or non-business books you’ve enjoyed recently?

CINDY: I’m a big fan of anything by Brené Brown. Also Daniel Goleman’s Emotional Intelligence. And I love biographies; the last great one I read was Becoming by Michelle Obama.

What makes you roll your eyes every time you hear it?

CINDY: Any form of hypocrisy – when someone says one thing, but act differently. Also watching company politics win over doing the right thing.

What’s the one condiment you could never live without? 

CINDY: Salt. Can that count as a condiment? I love salty foods.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

5 tips for building a thriving community from scratch

Those pics up there? That was me when I was a kid. I was the third of four children born to immigrant parents who still don’t speak much English. We were just trying to make ends meet, and life was pretty simple – food, school, and of course piano.

American ways were quite foreign to us. I still have to make my fingers into a “b” and a “d” to figure out where my bread plate and drinking glass go, and I was told Westerners weren’t trustworthy since they often said things they didn’t mean, like “Let’s have lunch” and not follow through. Or “How are you,” but not wait for an answer.

In 8th grade I was 4’6” with a home perm, heavy bangs, and thick glasses. We didn’t have much money, so I had three outfits; I wore each for two days in a row before rotating. There are kids who don’t mind these “limitations,” but I wasn’t one of them. I desperately wanted to fit in, but this was tough: even beyond my awkwardness, I was pretty unremarkable. I’m one of the few people I know who had virtually no activities in high school (I do know every episode of Gilligan’s Island, though). Plus, as with many families back then, parents didn’t talk about “adult things” to kids. All this means I didn’t really begin to interact comfortably with adults until I was about 30. 

Fast forward to today: I’m on my fourth startup, all of which have incredibly strong communities with networking that’s core to their success – ChIPs (5,000 members and 19 chapters around the world), RPX ($0 to $100M and IPO in less than three years), SaaStr (world’s largest b2b software community), and Operator Collective. How does someone so socially awkward build such thriving communities? In many ways not being a cool kid growing up was the perfect training ground for constructing communities and building startups. Here are five tips.

1) Find your niche

Communities and products succeed because they have a focus. People need a personal connection, which might mean choosing an area that’s ignored or overlooked. ChIPs started out hyperfocused on women in patent law (there weren’t many of us). Only after nailing that niche did we expand to women in law, tech, and policy. The venture world typically revolves around VCs and founders – so at Operator Collective, we put operators front and center.

Think about my awkward former self who just wanted to fit in. What if I’d had a community of Gilligan’s Island Aficionados Who Love Velour? I would’ve fit right in and had a core group to identify with. Find an initial niche or addressable market and expand from there.

2) Start with the bellwethers

The first thing everyone wants to know is who’s involved. Having not naturally been a people magnet, I learned to involve the people others do want to hang out with, and build from there.

If you’re hosting a conference, the obvious way is to begin with the speakers. Find an anchor and build around her. How do you get that first speaker? Try starting with a “two-fer” – find two speakers with a connection or friendship. If someone can combine a speaking engagement with seeing people they don’t often get to spend time with, they’re more likely to say yes. At Operator Summit, we invited fantastic speakers, but paired them each with a friend – like Eric Yuan with Jennifer Tejada, and Claire Hughes Johnson with Leyla Seka. This also applies when building a customer base: Garner a few respected companies/leaders as early adopters.

3) Be deliberate from the first engagement

You always have to make people feel comfortable – including those who don’t often join in. Last September, we put together Operator Summit in just 4 weeks. We knew we wanted a high percentage of women and people from underrepresented backgrounds, so we were public with that intention and deliberately reached out to people in those categories. It wasn’t a women’s conference or one for people of color, but we ended up with 80% women and 50% people of color.

This was another place being socially awkward helped. What would it take to get me to come to an event that’s full of people I didn’t know? A personal invitation, first of all – not a bulk mailing. Plus we asked those who were coming for names of contacts who might be interested, and then specifically mentioned the referring friend in that invitation. By the time you get to a SaaStr Annual size of 20,000 attendees, personal invitations aren’t always possible, but you can still do it selectively. The same goes for selling a product. Each interaction should feel personalized, so every prospect gets the sense that you are connecting with them as an individual and understand their needs.

4) Make it easy to participate

When you’re selling a product, you make it easy to buy. When you’re putting together a community, you make it easy to join. Start with scheduling. We have a lot of women with young kids in our Operator Collective community, so we try to schedule meetings and events at family-friendly times. Operator Summit, for example, started at 10 and ended at 4:30. When we have update calls, we try to schedule them for when we know people have finished dropping off kids at school, over lunch, or during a commute time. If we’re scheduling a group, we’ll often send a poll to ensure a critical mass.

The other key is to give people a role. It can be scary to walk into a new meeting or conference, so introverts like me prefer to have a task. At SaaStr Annual, “braindates” are wildly popular. At Operator Summit, we encourage people to sign up for our small group Office Hours.

5) Obsess over every detail

No matter what you’re building, you can never assume people will buy, join, or participate. You have to make it worthwhile, which means obsessing over every detail. What’s the mix of people, who will they meet, and what will make them come back? What kind of content will you provide and where will everyone find value? What’s the reg process, what about dietary restrictions, and what kind of swag? Obsess over every detail, from how they buy to how the product is delivered to the entire user experience.

Get Building

From the day we enter the working world and actually well before the need to network is hammered into us. We have to put ourselves out there and expand our connections in order to advance our careers. But communities can be a haven for the socially awkward: a place for people to find their niche and feel comfortable. And if this kid can grow up to be a super connector who builds successful network-dependent companies, I’m here to tell you that anyone can.

P.S. If you want to see my awkwardness in action, join me on March 11 at SaaStr Annual, where Leyla Seka, Lexi Reese, Elisa Steele, and I will do battle in an unscripted debate to determine the #1 secret to building high-performance orgs. I’m terrified already.