Ariana Sokolov co-founder trill project interview
Op-ed Overview
The pandemic has been a lonely time for LGBTQ+ youth for those who do not live in supportive households, making the need for inclusive spaces outside of the home even more important. With the pandemic, connecting with people outside of the home has been particularly difficult and we’re seeing youth turn to safe digital spaces as an alternative. I’m reaching out on behalf of Apple to introduce you to Trill Project, an app created by a talented, up-and-coming teenage developer, Ariana Sokolov. The young, LGBTQ+ ally created the app to ensure her best friend, who came out as bisexual, had a safe space online to express herself.
After hearing how hard it was for her friend to come out, Sokolov developed Trill – a combination of the words true and real – as an anonymous social network with no usernames (it uses various colors instead!) where everyone can freely and safely express themselves. Created by teenagers passionate about coding, the app provides a supportive community to make new connections and have authentic conversations.
Timed to April’s Sexual Assault Awareness Month, Ari can draft an op-ed that speaks to:
How the Trill Project creates a safe space for the LGBTQ+ community and why that is so important for this community specifically during April’s Sexual Assault Awareness Month
Her allyship to the LGBTQ+ community and inspiration for creating the Trill Project
How she came to become an advanced coder at such a young age
How her experience at Apple’s Worldwide Developers Conference and Apple’s Entrepreneur Camp built her coding skills
photos: https://drive.google.com/drive/folders/1x-SR7fAL5TWniGQ5NXtI_NnMpXAPTEeo
Can you tell us a bit about your background and what you were doing professionally before launching Trill Project?
I started coding when I accidentally walked into a computer science class at a summer camp when I was eight years old. I loved getting to combine my interest in math and design to create something from scratch, and this is what drew me to app development. Growing up, I used the coding resources Apple provides online to teach Swift classes to myself.
Eventually, I was awarded a student scholarship to the Apple Worldwide Developers Conference (WWDC). And my love for developing apps only grew stronger. Through this, I was able to unlock a community of fellow app developers that loved to create apps that impacted the lives of others. I was privileged to have the support of Apple engineers in labs and attend talks at WWDC that were instrumental in allowing me to become the app developer I am today.
I launched my business when I was 16 years old. Before that, I founded my own app development company and was working on projects for a variety of clients with my work being recognized by Apple, South by Southwest, and the U.S. Congress.
What was the “lightbulb moment” for Trill Project? What inspired you to start your business and pursue this path?
After hearing about my friend’s struggle coming out as a bisexual teen, I rallied together my Girls Who Code Club, and we sent out an anonymous survey to LGBTQ+ teens across Tumblr. We asked users, “What would you say if nobody knew you were saying it?” Through grassroots marketing strategies, we received hundreds and then thousands of responses to this survey. Responses trickled in around stories of feeling unheard, isolated, and alone.
We were stunned to see that many LGBTQ+ teens felt this way, especially in toxic digital spaces, so we decided to address the mental health issues affecting the LGBTQ+ community. After interviewing LGBTQ+ teens in our high school and learning from our friends how difficult their coming out experiences were, these early connections in customer discovery, who believed in my team and me enough to share their stories with us, became our first beta testers. Trill was designed collaboratively with 10,000 beta testers, and our users have trusted us from day one to listen without judgment and build this community for them, with them.
After working on Trill for a bit, we were accepted into Apple Entrepreneurship Camp. Here we were able to get tremendous feedback on the design and structure of our app to make it more meaningful to our users. We also learned how to integrate Machine Learning technology that would direct users to relevant crisis resources. These improvements that we made over the course of the program were very important to improving Trill.
An entrepreneurial career path is so special because it allows you to identify real problems in your life, like my friend’s struggles with her identity, and take action. I didn’t set out to be a founder necessarily, but I did seek out to solve a problem for my friend. And now I’m able to create technology that is used every day by my classmates, the online communities I belong to, and my generation as a whole.
Did you write a business plan? If so, was it helpful, and if not, what did you use to guide your business instead? Why did you take that approach?
My team and I participated in the Technovation Challenge, a global competition encouraging female-identifying high schoolers to build an app to solve a social problem. Through this, we were able to write our first business plan.
In the words of Former President Dwight D. Eisenhower, “Plans are useless, but planning is indispensable.” With regard to Trill, we actually have pivoted and evolved our business tons since participating in Technovation. That said, the process and exercise of taking time in the early days of our launch to consider moderation at scale, paid marketing campaigns, revenue strategies, and company culture was incredibly useful. If anything, writing a business plan gave us an opportunity to start thinking about some of the tough questions around building a business like how you make money and how you will grow community. Even if we didn't have all the answers when we first made our business plan, it gave us a solid foundation.
The primary guiding force we’ve always used when building our business (more than any business plan) is real-time user feedback. We are strong advocates for practicing collaborative and inclusive design processes that are user-centric. We’ve maintained a robust beta tester community with regular surveying, interviews, and focus groups to make sure we are building a product that users actually need, want, and are finding value in.
How did you come up with the name Trill Project, and what are some of the things you considered during the naming process?
Trill is a combination of the words true and real. And Trill Project is an anonymous social network for mental health peer support.
While it may seem counterintuitive, our experiences with Trill have given us the unique empathy and insight that anonymity and stepping away from whatever identities constrain you in the real world can actually allow you to more fully discover your true and real self. On Trill, we turn social media on its head. We replace followers with friends, emojis with True feelings, and selfies with Real people.
We allow users to unlock their most authentic selves in a digital world, and it doesn’t happen overnight. The movement to make the internet a safer and more kind space for people from all walks of life is an ongoing process and project. It’s Trill Project.
What were the immediate things you had to take care of to set up the business?
Immediately after coming up with the idea for Trill, my first action item was to build out a team. My team and I believe in capitalizing on our strengths and hiring for our weaknesses. Personally, I am a technically minded individual and enjoy software development, graphic design, and product management. So I brought on a co-founder who was more inclined towards the world of operations and could handle marketing, external relations, and sales down the line.
We worked right away to build team culture, setting expectations around responsibilities, commitments, and values. We did this by establishing workflow tools (GSuite, Trello, and Slack), setting up anonymous surveys for internal feedback, and identifying goals or OKRs for a given work sprint. We also collaboratively wrote community guidelines and strategized together on brand identity and company vision documents. With regard to logistics, we also had to set up our website, our social media channels, officially incorporate, and bring on an accountant and lawyer to advise us.
What research did you do for the business beforehand?
We were lucky to participate in an accelerator program in the early days of Trill. This gave us an excellent community right away to tap into for answers to questions around our business. We would recommend accelerators and incubators for first-time founders because it provides a valuable sense of structure, accountability, and routine. Additionally, you will be able to connect with other founders who can empathize in your journey and mentors and experts who are motivated to work with you.
How did you fund Trill Project? What were the challenges and what would you change? Would you recommend your funding route to other entrepreneurs today?
We have been bootstrapped and only raised capital from equity-free sources such as pitch competitions and incubator programs. For us, this was the right decision and we wouldn't have changed anything around our fundraising journey. Given that we weren’t ready to work full-time on Trill and wanted to finish our college degrees, bootstrapping gave us the flexibility to run the business on our own terms and not feel pressured to grow in ways that weren’t authentic to our mission.
I would recommend that founders take a critical look at what their ultimate goal is for their business. Do you want to grow very quickly? Is this a side hustle? Are you mission-oriented? Do you need capital to hit these goals? And then make educated decisions around fundraising from there.
Do you pay yourself, and if so, how did you know what to pay yourself?
At this time, no one on Trill’s team takes a salary as we are all also still full-time students.
How big is your team now, and what has the hiring process been like? Did you have any hiring experience before this venture? If not, how did you learn and what have you learned about it along the way?
Our team is now over 30 high school and college students from around the world all working as volunteers at Trill. Neither of us had any formal hiring experience since we started this venture so young, and for us the hiring process is something we put a lot of thought and care into.
We recruit for our “trillternship” every new semester in the school year and during the summer. To do this we tap into women in tech groups we are a part of, personal connections, and outreach on campuses. We have a written component and interview process for all interested candidates. We evaluate possible hires not only based on their skill set but also their knowledge of Trill, support of our mission, and fit within our company culture and values.
We’ve learned that it is critical to interview not just for skills but also for this mission alignment. Trill is a remote-first team, and most of us have never even met in person. Everyone is a volunteer. And so it’s important that we all like each other and the work that we’re doing. We conduct regular team satisfaction surveys and host a variety of team bonding socials such as movie nights, game nights, and showcases of our work. Our team is like a family, and we all support each other not only with our endeavors with Trill but also with our other academic and professional commitments and our own mental health and wellbeing.
We are proud that our team is Gen-Z powered, BIPOC-owned, and majority female engineers.
Did you hire an accountant? Who helped you with the financial decisions and setup?
We do have a bookkeeper who we are so grateful for! We would recommend finding and investing in a bookkeeper early on to keep all your expenses, taxes, etc. organized and in order.
What has been the biggest learning curve during the process of establishing your business?
Learning how to manage running a business with also being a full-time student can be a challenge. We’ve discovered the importance of prioritization and sacrifice. As long as you and your team are on the same page around time commitments, goals, and accountability structures, then it is totally possible to be both a student and a business owner. In fact, college can actually be a great opportunity to take courses that make you a better entrepreneur, tap into professors as potential mentors, and network with classmates who may be future co-founders, hires, advisors, customers, or investors.
How did you promote your company? How did you get people to know who you are and create buzz?
We first launched through a grassroots marketing campaign on Tumblr. From there, we have been growing our community organically mostly through socials. We have an active presence on all major platforms, and we work with influencers through our Trill Talks interview series who in turn promote our community to their audiences. We also have been able to achieve some wonderful press through various incubators and programs we’ve participated in, and we partner with other organizations as well for collaborative campaigns to mutually drive traction for each other’s products and missions.
Do you have a business coach or mentor, and would you recommend one?
Yes, we have a vibrant advisory board, and we definitely recommend building one out. Our business mentors give us tangible advice around our paid marketing campaigns, analytics tracking, moderation curriculum, and more. Additionally, our business mentors also offer less tangible advice sometimes, which can be just as useful. Such advice includes strategic input on time management, company vision, growth, and more.
What is one thing you didn’t do during the setup process that ended up being crucial to the business and would advise others to do asap?
We only recently have started formally setting and sticking to company-wide OKRs. We would recommend that all business owners get into an early habit of goal setting collaboratively with team members. This allows for transparency around milestones, organization around prioritization and delegation, and accountability to hit your business goals.
What is your number one piece of financial advice for any new business owner and why?
Protect your cap table with care. You will put so much time, energy, and love into your business, and you deserve to be an owner of the results of those efforts. Make sure you are building alongside teammates and investors who have been vetted and who share in your vision.
Anything else to add?
Download Trill Project, and follow us on socials. Trill has a full schedule of upcoming Pride Month events, including social mixers, panels, and moderator orientations specific to LGBTQ+ issues. We're collaborating on these events with a variety of mental health and emotional wellness experts, including Blue Fever, a pocket-sized support group app centered around anonymous, judgment-free journaling for every chapter of life. Interested individuals can RSVP for our fireside chat on Mental Health for the LGBTQ+ Community here and for our “Ask Me Anything” Panel here.
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How My Experience as an Investor Prepared Me to Be a Founder
Sage advice from a former venture capitalist.
Photo: Courtesy of Naomi Shah
It’s difficult to think of anything in my life that has required a wider or more dynamic skill set than founding and running a company. Unlike the way founding is sometimes described in pop culture and media, you can’t just have great ideas for products and services. You have to be capable of building a healthy company culture, understand how markets evolve, and anticipate what consumers will want in the future. Personally, the last year and a half have honed a higher tolerance for uncertainty, an irrepressible curiosity about our market and users, and the ability to communicate exactly what the company is trying to achieve to inspire all of our people.
While there’s nothing quite like running a start-up, I’m grateful that I had an opportunity to work at a venture capital firm before taking the helm of my company Meet Cute. Because VCs work directly with founders every day, they need to be capable of seeing the world from a founder’s perspective, which means identifying gaps in the market, crafting the right narratives about promising companies and ideas, gathering a lot of information from disparate sources, and making informed decisions in the face of incredible uncertainty. Due diligence is the central task for VCs, but they also have to be willing to take risks on the companies they believe in.
Investors and founders are on the same team. The best partnerships are often described as a marriage. That analogy rings true especially because of the ups and downs of founding over the years, which requires an intense trust in the people you work with that they will be there when you need it. Aligning on the direction of the company, personnel, and emerging market opportunities is critical. Ahead, I’m sharing some of the many lessons I learned as an investor that have also served me well as a founder.
Lesson #1: It all starts with curiosity.
Successful VCs are always on the lookout for companies that capture and hold their interest and users’ trust. Founders should want to work with investors who have thoughtful questions about their products and services, understand their industry, think differently, and believe in the founding team. It isn’t just a matter of cutting a check and hoping for a quick return. In turn, VCs should add value by thinking creatively about what the market will look like in the future and advising the company. I learned from shadowing partners at USV that the best VCs were also the best listeners, and think of VC as a service industry.
This starts with genuine curiosity about what a company does and what impact it could have on the world with the right guidance and resources. The average holding period for VC investors is eight years. This is a reminder that investors need to be mission-aligned as they will work with companies over the long term and are investing in the sustainable success of their portfolio companies.
VCs and founders should establish open lines of communication right at the outset. I’ve never been afraid to ask questions or contact experts who know more than I do about a subject, and these skills served me well as an investor and a CEO.
When I was at the VC firm, the best way to learn about early-stage companies was to work directly with them on forecasting, marketing strategy, fundraising, and other issues and consult with experts outside of the company to bring new perspectives to the table. The same collaborative mentality is an essential part of the culture at Meet Cute today. If we need to talk to an expert about something specific, we are not shy about asking and learning. Time and time again, smart people in the industry who we look up to make time for those who are genuinely curious.
Lesson #2: Make the best decision possible with incomplete information.
Early-stage investing offers unique benefits, such as the ability to identify innovative companies before other investors, help steer those companies in a positive direction, and ultimately secure more growth over time for taking on a much larger risk. These are all reasons why it’s no surprise that early-stage VC investments have surged over the past decade from $14 billion in 2011 to just over $47 billion in 2019. Early-stage investing is on pace to set a record this year. The first quarter alone saw greater deal value than the entire year in 2011.
Early-stage investing also comes with quite a few obstacles, and a lack of information is one of the biggest. Early-stage investors don’t have as much data about a company’s growth, operational efficiency, etc., so many of their decisions are based on pattern recognition and intuition. The founders of early-stage companies face similar constraints. There’s no playbook for what many of these companies are doing, so we have to be comfortable making decisions with limited information. Just as investors need to accept the fact that they will sometimes make the wrong call, founders should be willing to fail. If everything is going too smoothly, you should ask yourself if you’re scaling ambitiously enough.
All of that said, founders and VCs should be as fastidious as possible in their research. Due diligence as a core focus means putting in the time to learn and develop opinions and perspectives. But due diligence always has to be placed in the context of the realistic constraints you face, especially in building something completely new, and knowing what level of risk you’re willing to tolerate.
Lesson #3: Always tell your story
A company’s story is integral to its identity, and it serves as one of the most effective ways to reach your audience and let them trust our brand, galvanize employees around a common message, and attract the best investors. As an investor, I frequently told stories about innovative companies to convince my colleagues that we should back them, often in the form of an investment memo or a short and sweet presentation in a team meeting. I also helped start-ups craft their stories when they launched fundraising rounds or needed to prepare for board updates. Storytelling is the most powerful tool we have as humans and we know that the emotions of a story are remembered far better than facts.
Moreover, I’ve realized how sharing your story internally is vital to improving morale and helping employees rally around a consistent set of values and objectives. Gallup reports that only 27 percent of employees strongly believe in their company’s values, while less than half say they strongly agree that they understand what the company stands for or what sets it apart. By telling the company story and vision often and consistently, the team can rally around what they’re working toward and why it matters.
Reflecting on the last year, there is a significant overlap between my experiences as an investor and a founder. By making a conscious effort to understand how my experiences tie into and bolster one another, I hope that I can show where founders and the VC firms that support them can build stronger relationships and thereby more unique and impactful products in the world.
Photo: Courtesy of Naomi Shah
About the author: Naomi Shah is the founder and CEO of Meet Cute, a venture-backed media company that has produced over 300 original light-hearted romantic comedies in podcast form. The company celebrates human connection and the full spectrum of love with the core mission of having every person feel like they are reflected in Meet Cute stories. Since its inception in February 2020, the podcast has had over two million listens across over 150 countries and has been featured in the top 10 of Fiction on Apple Podcasts and Spotify.
Before starting Meet Cute, she was a member of the investment team at Union Square Ventures, a technology venture capital firm in New York, where she spent most of her time talking to companies in the consumer and well-being space. Prior to that, she was a macro equities trader at Goldman Sachs and studied mechanical engineering and human biology at Stanford University.
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How to Hire the Right In-House Legal Counsel (and Save Your Startup Money)
Timing matters (and earlier is better).
Photo: ColorJoy Stock
If you’re looking to hire legal counsel for your company, be careful. Just because you’ve found a lawyer who specializes in startups, doesn’t mean they’re the right legal counsel for you or your startup. Here’s how to evaluate whether a lawyer is right for you.
Experience Is Important
In order to reap the benefits of hiring an in-house counsel early, you need to hire the “right” lawyer. Look for someone who has worked in your industry, and if possible, in the particular type of business your startup is involved in, which will make their existing knowledge and experience transfer easily to the company.
The right lawyer should bring real-world considerations into any legal analysis and be able to assess and articulate risks without making a startup feel that all roads to achieving its business goals are blocked. If a particular course of conduct is deemed to be too risky to pursue, an in-house lawyer should be able to suggest safer alternatives to consider, balancing legal requirements with the needs (and vision) of the business.
Consider Culture Fit
Fit within your company culture is also important. Your in-house legal team should be adept at forming relationships with the other key members of your leadership team, so that they, too, see the lawyers as a helpful source of guidance and strategic input, rather than simply naysayers.
Timing Matters (and Earlier Is Better)
It is much easier for in-house counsel to be viewed by your management team as a “partner” and not a “blocker” when that person is brought into the conversation early and is part of discussions about the vision and path of the company. Bringing a lawyer on board when there are already fires to put out makes it harder hard to view them as the strategic partner they can be.
By bringing on the right in-house counsel early in your startup’s life, you can build a legal department that is not simply a “cost,” but a true strategic partner of the business. This paradigm shift can end up saving you money, angst, and reputational damage, and will ultimately lead you and your company to be more successful.
“By bringing on the right in-house counsel early in your startup’s life, you can build a legal department that is not simply a “cost,” but a true strategic partner of the business.”
—Amy Rowland, Founder of Varia Search
About the Author: Amy Rowland is the founder of Varia Search, a boutique legal recruiting firm that uses a bespoke approach to fill legal department roles. Prior to starting Varia Search, Amy was a recruiter at another legal search firm where she focused on recruiting for in-house legal positions. She has also held in-house roles at two international companies and a large New York City law firm.
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When Should Your Startup Hire a Full-Time Lawyer?
Psst… it may be sooner than you think.
Photo: ColorJoy Stock
Because an in-house legal department is commonly viewed as a “cost center” and not a “revenue generator,” startups are often advised that the answer to the question of “when should we hire an in-house counsel” is best answered by running a straightforward cost-benefit analysis. When that exercise demonstrates that the legal fees paid to outside counsel are greater than the cost of adding a lawyer to a company’s payroll, then it is time to bring on a lawyer to work in-house.
While this approach is appealing in its simplicity, it fails to account for a big portion of the value that an in-house lawyer (and ultimately, a legal team) can bring to a young company, the value that may be difficult to quantify. The right in-house counsel can be a strategic partner and a huge asset to a growing business. Here’s how to tell when you should bring on a full-time lawyer.
Save Yourself Headaches and Money, and Hire In-House Counsel Early On
Once the legal structure of a company (LLC, Corporation, Partnership, etc.) has been set up and the basic legal requirements for doing business have been met, many startup founders think of lawyers only as “clean-up crews:” people reluctantly hired from time to time when there’s a problem.
In fact, until confronted by a lawsuit or government investigation, many founders tend to view lawyers as obstacles to progress—people who are always telling you what you can’t do—and to want to avoid them for that reason. But lawyers can also provide useful perspectives to a founder strategizing how the company can achieve its goals while avoiding expensive pitfalls.
A good lawyer has been trained to anticipate issues that might arise and will put in place the safeguards that can help a company avoid those problems. Like the old adage, “a stitch in time saves nine,” this way of working obviously helps a company avoid extremely costly mistakes.
Learn From the Mistakes of Others, and Consult Legal Counsel Proactively
Protecting your business early on can save you 10x, 20x, or even 30x in legal fees if you have to hire legal counsel to clean up a mess. In Season four of HBO’s series “Silicon Valley,” an entire episode (“Terms of Service”) was constructed around a character’s failure to comply with the FTC’s Children’s Online Privacy Protection Rule (“COPPA”), estimating that that mistake—made without even realizing that a lawyer should have been consulted—left the company, Pied Piper, potentially liable for $21 billion in fines.
A quick consultation with a lawyer could have saved a lot of angst, even if it would have ruined the episode. As far-fetched as this scenario might be, it is unquestionably true that a lawyer can save a company money by minimizing its exposure to regulatory fines, along with lessening the likelihood of costly lawsuits and making sure the company’s intellectual property, reputation, and other valuable company assets are well protected—all of which add enormously to a company’s success.
Unfortunately, since these benefits represent savings that are difficult to quantify, they are not so easy to plug into a cost-benefit analysis, but that doesn’t make them any less important than the sum of all those law firm invoices.
“Can’t I Just Use Outside Counsel Instead of Hiring a Lawyer In-House?”
While outside counsel can certainly provide legal services, without context, a founder may miss the right opportunity to reach out for help (since you don’t know what you don’t know!). Even if you do think legal counsel would be helpful, the prospect of facing expensive legal fees may deter your from making the call until a concrete issue presents itself.
Giving an in-house lawyer a seat at the table early in a company’s development can mean fewer unpleasant surprises down the road. It can have other benefits as well, such as devising a strategy for utilizing outside law firms and judging when the most cost-effective choice is to consult outside legal experts, for example, to advise with respect to a specialized area of the law such as patent and other intellectual property matters, First Amendment issues, SEC regulations and the like.
When it is determined that outside counsel needs to be consulted, the in-house counsel team can manage that relationship, including negotiating legal fee rates and reviewing bills. If done right, this can also save a company money. Not only that, it will free up the team member who is currently managing outside counsel, which again can lead to cost savings or even revenue growth if that team member’s responsibility is normally to generate revenue for the company.
“While outside counsel can certainly provide legal services, without context, a founder may miss the right opportunity to reach out for help (since you don’t know what you don’t know!).”
—Amy Rowland, Founder of Varia Search
About the Author: Amy Rowland is the founder of Varia Search, a boutique legal recruiting firm that uses a bespoke approach to fill legal department roles. Prior to starting Varia Search, Amy was a recruiter at another legal search firm where she focused on recruiting for in-house legal positions. She has also held in-house roles at two international companies and a large New York City law firm.
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5 Things You Need to Know Before Raising Money for Your Startup
#1: You don’t necessarily need to do it.
Asking for money is rarely fun. But it’s especially tough—and often futile—for women. Why? We’re less likely to get a raise at work, even though we ask at the same rate as men. And we’re especially unlikely to get money for our startups since only 2.2% of all venture capital goes to female founders. (The percentages are even worse for women of color.)
Even for those women who successfully ask this question, it’s as I write in my book Startup Money Made Easy: The Inc. Guide to Every Financial Question About Starting, Running, and Growing Your Business, “seeking outside money is a daunting, grinding, tedious process.” It can go horribly wrong. But raising money can also go tremendously well if you do your homework, network like crazy, and get lucky.
Over the course of nearly five years of reporting and editing money coverage at Inc., I’ve interviewed many successful women founders. Some of them avoided raising outside money entirely; others have raised tens of millions of dollars. So if you’re ready to take the VC plunge—or to start off by asking friends and family to back your business.
Here are five things to know about raising money for your startup.
You don’t necessarily need to do it.
VC-backed startups like Uber, WeWork, and Airbnb get a lot of the headlines, but most startups never ask outside investors for money and many thrive regardless. Take S’well: Founder and CEO Sarah Kauss turned her high-design water bottles into a $100 million business without ever taking outside investment.
There’s an increasing number of women funding women.
While traditional VC has a long way to go to close the gender gap, there is a growing number of investment firms focused on women-led startups. Some examples are Arlan Hamilton’s Backstage Capital, Susan Lyne’s BBG Ventures, and Anu Duggal’s Female Founders Fund. Women founders, meanwhile, told Inc. that female investors often better understand their target markets.
Still, it’s often a slog.
“When you see company after company raising money, you get the outside-in perception: ‘It's not that difficult if they can do it.‘ But this is not the case,” Policygenius co-founder and CEO Jennifer Fitzgerald told me about her initial fundraising expectations. “It was a very fruitless and frustrating few months,” she adds. Fitzgerald and her co-founder eventually raised their seed round through small checks from about 50 friends and family members, “which is a painful way to do it, but we had to get it done,” she recalled.
It can also be exhilarating.
“Raising money was a year and a half of my life, and I loved every minute of it. Boy, was it grinding and difficult,” Christina Tosi, the pastry chef who’s now the founder and CEO of Milk Bar, told me last year. “You're going to war … and not necessarily in a negative way. It doesn't have to be argumentative.”
It matters who your partners are.
Don’t accept just any investment. As your business grows, you’ll want to make sure you and your investors can agree on what’s best for the business (unless you want to try to buy them out). As Tosi put it, “You can't do a good deal with bad people, and you can't do a bad deal with good people.”
About the author: Maria Aspan is an award-winning business journalist and an editor-at-large at Inc. Magazine, where she oversees money coverage and writes about startups, technology, finance, and gender. She has also covered business and finance for The New York Times, Thomson Reuters, and American Banker. At the latter, she served as national editor and covered the 2008 financial crisis and its aftermath.
This post was originally published on March 11, 2019, and has since been updated.
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Startup 101: Your Year One Essential Checklist from Above the Glass
On the precipice of launching your business? You'll need this checklist.
FEMALE ENTREPRENEURSHIP IS GROWING FASTER THAN EVER. BUT TO CAPITALIZE ON THE WHIRLWIND OF OPPORTUNITY, YOU NEED TO UNDERSTAND THE STORM FROM WITHIN.
Enter, Danielle Yadegar and Heather Serden, co-founders of the freshly launched Above the Glass, an online platform providing women in business with straight talk interviews with women in business and actionable take-it-to-the-bank advice. Like free downloads, because Above the Glass wants to see you succeed. They believe that, "without a doubt economic empowerment and the capability to start businesses should be available for all women.”
So, if you are on the precipice of launching, download the Startup Essential Checklist from Above the Glass, and get the engine on your business running.
To download the checklist, enter your information on the the form below and a link to the free download will pop-up. Good luck!
The 6 Personality Types Every Startup Needs
You're only as good as your team.
Your startup is your tribe.
You spend more time with them than you do with your family (#sorrymom). There are shared lunches and late hours and at certain points, you all wear every single hat. Because when you’re working to build something together, you switch hats, pants, shoes; the words “I can’t do that,” are not part of your vocabulary. In many ways each of you is the "ideal worker"-- something that gender and labor scholars have identified as the person who shows up early, leaves late, never says no, never gets sick, answers emails morning, noon, night, weekends, makes every meeting, is a go-getter, ad infinitum. These are employees who work hard and challenge themselves on a daily basis. In a dream world, every team member of your start-up is that person.
Here on earth however, there are specific people that fit better into certain roles and make the squad function like a well-oiled machine.
THE VISIONARY
Often the CEO. They think big and small, they see far ahead but also catch the tiniest of details right in the moment; the little things you would never even notice. Nothing gets past them, but it's because the Visionary knows how they want to see their vision executed. Thinking outside-the-box is one part of their supernatural abilities. They are highly-functional, fast-paced, and fastidious. "The ways in which people consume everything," says Jaclyn Johnson, Founder and CEO, "has changed significantly. So if we are not evolving, we are not doing our job. We want to help advance the new creators, the thinkers, the other dreamers. And we've only just begun. We don't want to create a pipeline of new workers, we want to burst open the whole channel and see what happens."
"We don't want to create a pipeline of new workers, we want to burst open the whole channel."
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THE CLOSER
The Closer has perseverance and structure like you wouldn’t believe and solutions to any problem. In part it's because they’ve "been, there, done that"— and bring experience from many industries to the table. They know how to work a conversation to their advantage. They are great at team management and turning ideas into action items— especially at executing the vision of the dreamer. Bess Wyrick, Senior Events Producer at Create & Cultivate is our Closer. "It's just not an option," says Bess, "to not get it done. And if you have that attitude at work, don't expect to go very far. You take an idea, or you have an idea, and you make it happen. If it doesn't look or feel right, you do it again. We've nixed entire concepts day-of the conference because it wasn't perfect. I mean, look, there's no wrong way to enjoy a glass of wine, but there is always a smarter way."
THE UNICORN
Part social butterfly part go-getter. The unicorn of the the bunch is known for making magic, and doing it with pep and a smile. Hope Evans, Accounts Director. is as gregarious and unicorn-like as workers come. From meeting with clients to working with talent, she's the ultimate team player. Because part of that sociable charm is the inherent caregiver— keeping team morale up even as stress rises. "It's not magic," says Hope, "it's about chemistry, about making a room feel at ease by making every person feel taken care of-- from talent, to speakers, to sponsors, to everyone who has purchase a ticket. If you treat everyone as an individual, your company will standout as a whole. Especially day of the conference, it's a runaway train that you just have to ride, and make sure everyone is riding along with you. No one falls off this train. No one."
THE NO-NONSENSE TYPE
Follow-through is one of the main traits of the no-nonsense employee. Enthusiastic but firm, the no-nonsense type is a bit like sandpaper— firm, tough, but smooths out anything. For C&C that’s Steph Chang, Director of Events. She’s a nose-to-the-grindstone, no-nonsense worker that will always be crystal clear on what she needs-- especially if she doesn't like the way you're doing something. "When you're planning events you are dealing with so many vendors, sponsors, the venue, parking, food, people, everything-- everything where you can't see the work, a ton of work went into it. So you have to be firm, tenacious, get everything in writing. If you miss one detail, Rome topples. And we've already learned that lesson. From big picture, to the nitty-gritty, nothing is falling apart on my watch, even if it means a sternly worded convo, or two."
THE HEART
You know the person. They're always saying yes. They are there to talk out an idea with you, jump in, give you their thoughts, and share their best ideas-- all the while grinding out what's on their own plate. The Heart sticks on brand and is less concerned with credit than with crafting the right message. At times our Heart, Director of Social Media, Priscilla Castro is a headphones on and head down worker. But tap her shoulder and she's right there with you. "A startup like ours is about the collective, so even though my job revolves around spreading the word, it's important that everyone else on the team is on message as well. Which, yes, means breaking from my to-do list and jumping in where I'm needed."
THE PISTOL
A bit of a worker bee that’s self-motivated, the Pistol is a straight-shooter that fires off ideas, and gets work done at the same speed. The Pistol doesn’t wait for ideas to come to them, nor do they second-guess themselves. Editorial Director, Arianna Schioldager says, "We don't take what we're doing lightly, and the idea that our conferences and content are encouraging young entrepreneurs to take major leaps fuels our days and nights, but that responsibility means we have to always be innovating. Always providing the best. That means tons of ideas. Plenty of which get thrown out. But you have to keep shooting, and shooting straight or we lose the trust of our audience and attendees. We shoot the moon every single day, and even though this makes for tough moments, no one ever said landing the moon was easy."
"We shoot the moon every single day, but no one said landing the moon was easy."
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Dress The Part: Corporate, Startup, or Freelance?
If you're going to work the part, you should also dress the part.
Office culture has changed a lot of the years, and it’s left some of us a tad bit stumped on how to dress. #help. Just when does one wear a power suit? And what’s the deal with casual Fridays, when jeans have become an every day part of the work week? You’ve got enough to worry about in the morning without getting held up by your closet.
So, we asked for a little help from Bar III, the fashion-foward line from Macy’s, to figure out how to get dressed (and out the door in time) in the AM. With modern pieces that fit into any office environment, you’ll look oh-so-profressional— whether you work in a corporate environment, spend days and nights at a start-up, or you’re on that freelance hustle.
Start with a basic pair of black pants and top from their line, and follow the below to figure out the office culture style that fits your personality best. It’s a no-fuss solution to setting the bar higher.
