The biggest question we deal with on a daily basis is “how much does insurance for startups cost?” All of our clients want to know exactly what they’ll have to spend and how long it will take. They all expect an immediate answer, and can you blame them? The startup world moves at a blistering pace.
But the honest answer to both questions is: “it depends.” And an even more complete answer would be “it depends how you look at it.”
That’s probably not the answer you were hoping for when you clicked on this post, but a little background on the underwriting process will help clarify why this is true. Most underwriters work very hard to carve out distinct “boxes” into which they try to fit all of their policies. Fitting policies into certain risk profiles makes their life easier, which underwriters really like.
And while we’re on the subject, underwriters do not work at the same level of intensity as the startup world. It’s much more of a 9:00 to 4:30 scene in those offices.
The problem with this approach is that it simply doesn’t work with startups. Startups are disruptive. Disruptive things don’t fit in boxes. Square peg, round hole…you understand what I’m getting at.
This is why getting insurance for startups can be a somewhat lengthy and interactive process, and why policies might cost a bit more than your average ice cream shop. In fact, if the underwriting analysis takes longer than expected, take it as a compliment. You’re breaking their neat little boxes!
So getting back to the original point and the title of this post, is insurance just another cost or a valuable investment? It depends how you look at it. The truth is almost any broker can get you a basic policy very quickly — but it’ll likely be so riddled with exclusions and limited in scope that it’s basically worthless. That right there is insurance as a “cost” — just a quick “box-checking” exercise.
However, getting real coverage takes a little more time and will cost you a little more. This is because your broker has to engage the underwriters and really help them understand why they shouldn’t freak out if your company doesn’t fit into a particular box. If it’s done right though, you’ll get actual coverage that extends to protect your workspace, all of your operational activities, and even events that are totally unforeseen and out of your control. This is a real asset beyond just having great coverage.
As a startup, one of the biggest challenges from a marketing perspective can be establishing authority in your space and credibility with your target market. Being able to advertise that you’re completely insured makes that job way easier. You may even be able to leverage your insurance policies into money-back guarantees for your customers, driving up conversions and increasing your top line!
Insurance can be just another cost of doing business, or it can be an investment in your favor. It can be quick, cheap and ineffective, or just like your company, it can take a little time to create, but add massive value in the end. The choice is up to you!
Stacy Spikes believes that successful entrepreneurs don’t understand the word “no.”
“I think the people in this room have a part of their brain where they don’t quite hear the word ‘no’ properly,” said Spikes, speaking to a room packed with people eager to hear how he had cofounded the movie subscription service Moviepass. “You have to have that. There are some people in the world that hear the word ‘no’ and they go, ‘OK.’ And that’s it for them.”
Spikes believes that every time an investor says “no” to a pitch, they’re only refining what it will take to get a “yes.”
“Eventually, what they’ve done is that they’ve sharpened your pitch so incredibly that there’s nothing being thrown at you that will stump you,” says Spikes, a longtime member at WeWork Soho West. He recently spoke at a WeWork Labs event that drew more than 70 guests to WeWork Dumbo Heights.
Spikes has heard “no” plenty of times. When he was fired from a film production company in 1997, he rented a small cubicle at the Tribeca Film Center. There he came up with the idea for Urbanworld, which in the past two decades has become the world’s largest film festival for minority filmmakers, actors, writers, and directors. The five-day event takes place in late September in New York City.
In 2011, Spikes and business partner Hamet Watt founded MoviePass, which allows subscribers to see a movie a day for a monthly fee of $9.95. Spikes says they first hit upon the idea for Moviepass in 2005, and despite being told “no” for six years, he and Watt refused to throw in the towel.
Spikes says their inspiration came from art-house theaters in New York City that let customers see an unlimited number of movies for a flat fee. They racked up roughly 23,000 subscribers under their original business model, which charged an average of $35 a month. This helped them raise almost $14 million from early investors like AOL Ventures and William Morris Entertainment.
Then MoviePass caught the eye of Helios & Matheson Analytics, a data analytics company that bought the business in 2017. Spikes stayed on to chair the board of directors until early this year, leaving before the stock took a hit in the media and saw its stock price plummet.
Spikes currently working on a new venture, though the 50-year-old entrepreneur has remained tight-lipped about what it will be.
Have the perfect data
Spikes describes MoviePass as a data-driven company that collects information on individual subscribers, like what movies they are watching and where they are located. He believes that the most important thing for a company’s success is having accurate data and has made a point to remember this every step of the way.
“The truth is, if your data is off, you’re just believing your own hype and you’re lying to yourself,” Spikes says. He adds that he’ll often share his data with people outside the industry, just to make sure that the numbers are persuasive
His advice to entrepreneurs starting their own company echoes this, urging people to make sure their numbers are accurate and run their presentations by several people before going too far.
“Those things are critical because if you’re not all buttoned up, you’ll pay a price for that,” he says. “And sometimes you can’t walk back in those doors several times.”
“I can’t go in the mirror before I walk into that conference room going, ‘OK, you’re black, but you can do it!’” he says. “I have to walk in going, ‘I got a great idea that you should fund.’”
He urges entrepreneurs to continually “ram the gates.”
“You might be that person who gets through the gates,” he says, “and then people are going to look at you and say ‘Well, if Stacy got through, maybe I can get through.’”
Use the right resources
Spikes looks to resources like DocSend, a content tracking solution, to help him get a read on people he’s trying to pitch. By allowing him to see how long investors spend on each slide in his initial pitch deck, DocSend gives Spikes some foreshadowing into what potential clients are thinking.
“It’s a great tool to help me in the [fundraising] process because you don’t want people who are going to waste your time,” he says.
He also advises entrepreneurs to figure out a schedule that promotes productivity. Spikes keeps himself moving forward by breaking up his week. He does certain things on certain days — Mondays are dedicated to tasks and projects, while Thursdays are for finance.
“This makes it easier because there are certain things that you don’t want to do,” Spikes says, “so you’re not stuck doing those things for your whole week.”
Spikes considers himself a voracious reader of biographies, a genre he sees as a handbook of sorts. He likens reading a biography to “an executive coming and sitting with you, telling you exactly how to do things.”
At the end of the day, Spikes stresses that an entrepreneur’s best resource is themself.
“Be smart,” he says. “Find your way into the door and into the conversation. Play the part like you’re there to win. I have a blazer in the drawer because you gotta be ready to roll. You have to think on your feet and use whatever you got to get through the wall.”
When Manchester United midfielder Juan Mata reflects on his more than decade of playing professional soccer, he says that the trophies and titles have been gratifying. But it’s the sport’s potential to change the world that compels him the most.
“Thanks to a career in football, I’ve been able to travel to many parts of the world, and what I’ve come to find is that this sport really brings people together and has a profound impact on the next generation of boys and girls,” said the Spanish player, speaking to a crowd of soccer fans at Colombia’s WeWork Usaquén.
He realized that soccer could help transform lives at the local level by funding initiatives to battle intractable problems like gender inequality and youth unemployment.
“We started Common Goal for our love of football and as a way to make an impact, a movement we started some 10 months ago,” said Mata.
“At Common Goal, we use football to improve the lives of young boys and girls, and that’s why why are here with WeWork,” said Mata. “We share the same mission of bringing people together. We are thrilled to partner with a company like WeWork to help support us and our mission.”
After joining a panel discussion at WeWork Usaquén, Mata settled in to watch Spain take on Iran in a match during the World Cup. Members there said watching Mata cheer as his Spanish teammates won the match was a once-in-a-lifetime experience.
This was one of dozens of viewing parties held at WeWork locations around the world as the month-long World Cup competition unfolded. In Berlin, Common Ground co-founder Thomas Preiss spoke before 150 people gathered to take in the Germany vs. South Korea match on June 14. Half a world away, members at WeWork Seoul cheered their team to victory.
As England powered its way to the semifinals, members in London gathered for a series of events leading off with a June 18 panel discussion led by WeWork member Akin Solanke-Caulker, head of the sports talent agency the Athletic Network. Before watching the match at WeWork Old Street, Solanke-Caulker regaled the crowd with tales of negotiating deals with some of the biggest names in soccer, rugby, and track and field.
On July 10, the day France took on Belgium in the semifinals, Miami’s WeWork Security Building hosted a viewing party featuring WeWork member Soccer Shape, a fitness plan started by members of the Miami Football Club that incorporates drills and exercises used by top teams. Members got to kick a ball around before settling in to watch the big game.
When Larry Irvin and Kristyna Jones met at Mardi Gras in 2011, they immediately connected through their shared love of hip-hop and rap. Then the conversation got more personal: Jones gave Irvin her perspective of working in community development in New Orleans both before and after Hurricane Katrina, and Irvin shared his story of growing up as a black man in New Orleans with questions of self-identity.
“Young black men are perpetually trying to figure out who they are supposed to be, because the representations both in our neighborhoods and schools are, a lot of the time, negative,” Irvin says, citing high rates of incarceration and unemployment.
Irvin and Jones came up with a potential solution: getting more black men into the classroom.
“There’s a particular demographic, even within the demographic of black men, who aren’t attached to their academic experience,” says Irvin, 36. “College is something they’re told to do, but not with any purpose behind it.”
Together, Irvin and Jones founded Brothers Empowered to Teach, a nonprofit that urges people of color – particularly black men – to explore careers in education. It seeks to generate a network of teachers who serve as role models for the next generation.
Starting with just seven fellows in 2014, the organization has since grown to have over 40 participants between New Orleans and Baton Rouge. It has partnered with over 10 schools across New Orleans and Baton Rouge, and four graduates of the program teach in New Orleans public schools.
Irvin himself is a former substitute teacher, a job he held while coaching high school football. He discovered that he had a special connection with many of the kids.
“Having grown up in some of those same neighborhoods that they did, there was a cultural connection,” says Irvin. “It started to seem like I was meant to do this work.”
The organization offers two programs for future educators: a one-year program tailored toward college graduates and those changing careers, and a three-year fellowship geared toward current college students. The organization’s teachers get together on Saturdays for professional and personal development workshops.
“We have intimate conversations about things like redefining what masculinity looks like, around male-female gender relationships, and around sexual orientation,” says Irvin. “We’re trying to create a better version of the individual, which in turn turns them into a great educator.”
Brothers Empowered to Teach got a big boost last year at WeWork’s Austin Creator Awards. When it was announced that the organization had won $130,000, Irvin was greeted with a standing ovation from the crowd of more than 2,750 people.
A WeWork member, Irvin uses the company’s spaces when he travels, especially to cities like Austin and Washington, D.C.
While Brothers Empowered to Teach has so far worked with only male teachers, the organization recently opened up 30 percent of its seats to women of color.
“It is really beautiful to see our fellows attached to something, approaching education with fervor and excitement,” Irvin says. “We’re trying to change the narrative and reignite a lost reverence for the education profession.”
When former Marine Corps captain Zach Iscol went out for beers with his former commander, they talked about the 33 men in their battalion who had been killed in action in the Iraqi city of Fallujah in 2004.
Unfortunately, tragedy did not end there.
“[We] realized that there’d soon be a point in time when we’d lost more Marines to suicide than to enemy action,” Iscol says. “It’s an epidemic.”
That moment six years ago led to the founding of theHeadstrong Project, a New York-based nonprofit that helps veterans heal the wounds that have plagued so many of their lives as a result of the experience of war and beyond — in particular, the effects of post-traumatic stress disorder (PTSD).
Iscol decided he wanted to do something about this problem by providing veterans with top-notch mental health care, free of charge. He joined forces with two staffers at Weill Cornell Medical College in New York City: Ann Beeder, a clinical psychiatrist who has treated patients suffering from trauma for more than two decades, and Gerard Ilaria, a licensed social worker and health care professional who has dedicated much of his career to caring for people with HIV. Together they co-founded Headstrong.
At Headstrong, post-9/11 veterans can receive confidential treatment at no cost, and without bureaucracy or paperwork — or the stigma that often surrounds mental health counseling.
“These are good people who have to make impossible life-and-death decisions,” says Iscol, 39. “And you have to live with those decisions. And when you’re a good person it can be really hard to live with those decisions.”
There is no cap to the number of counseling sessions veterans can partake in. According to Iscol, the program currently has more than 500 veterans in treatment across 18 cities.
“We’ve treated over 700 veterans in six years,” he says. “And we’ve had zero suicides that have been in our treatment program.”
Ilaria said that helping veterans in the workplace is a big part of the program. It’s an important part of getting their lives back on track.
“Veterans make excellent leaders and they’re great on a team,” says Ilaria, 57. “But they can’t really do well at their job if their mental health isn’t in order.”
Todd Bowers, director of WeWork’s Veterans Initiative, says that Headstrong is a valuable resource for veterans and their loved ones.
“By providing cost-free, bureaucracy-free, and stigma-free treatment for the hidden wounds of war, Headstrong and their incredible team have helped to shape the narrative around post-9/11 veterans and their families by showing that the right help at the right time can heal anyone,” says Bowers, who was a staff sergeant with the Marine Corps serving in Iraq and Afghanistan.
Life ‘changed in the blink of an eye’
One of Headstrong’s success stories is Joe Quinn, who was a year away from graduating from West Point in 2001. But a week after he received his senior class ring, a celebratory event, the World Trade Center was attacked. “It all changed in the blink of an eye,” Quinn says.
His 23-year-old brother Jimmy was on the 104th floor when Flight 11 hit the North Tower on September 11, 2001. A graduate of Manhattan College, Jimmy was working for Cantor Fitzgerald, a financial services firm whose offices occupied the 101st through 105th floors. The company lost 658 employees, including Quinn’s brother. “All of the sudden there was this punch in the face,” says Quinn. His classmates at West Point realized, as Quinn puts it, “that this is why we’re here.”
He graduated as a lieutenant and joined the Army, serving two tours in Iraq before being deployed in Afghanistan as a civilian counterinsurgency advisor for General David Petraeus. He then earned a master’s degree in public policy from Harvard’s Kennedy School and returned to West Point as an instructor at its Combatting Terrorism Center.
For 14 years Quinn held onto a complex set of feelings wrapped up in the grief of his brother’s death and the experiences surrounding the deaths of many of his fellow soldiers. Quinn, now 38,described in a personal essay how his feelings compounded and manifested repeatedly over the years: a heaviness in his chest; a warm flush of blood rising to his head; a sharp jolt of heat stinging his heart. He had PTSD. At first he thought he felt guilt, but eventually realized it was shame. “I placed no value on myself, which led to depression and aggression,” he wrote. “I thought going to war would save me, but it made things worse.”
After referring numerous friends to Headstrong, Quinn decided in 2015 that it was time to seek help for himself there.
Quinn now serves as the executive director of Headstrong, working from his office atWeWork 42nd Street. “I jump out of bed [to go to work],” he says. Quinn, who grew up in Brooklyn, alsocontinues the annual tradition of the “Jimmy Quinn Mets Game” in which he and early 200 family and friends go to Citi Field in Queens for a ballgame.
Quinn isn’t the only member of Headstrong’s management to seek help at his eventual place of employment. Dustin Shryock, the nonprofit’s director of operations, served two tours in Iraq. During his second deployment in 2007 and 2008, he says his unit set a new record for the number of days in a row during which they were engaged with direct fire, indirect fire, mortar fire, and grenades.
Like many veterans, Shryrock, 35, hadtrouble transitioning back to civilian life. He had left his home state of California for New York City, enrolling in graduate school, but was doing poorly, and began to notice that he was experiencing anxiety and depression. “I was not going home anymore. I was staying out all night. I quit responding at work. [NYU] was about to kick me out because I’d rather be at the bar than at class,” says Shryrock, who also works from WeWork 42nd Street.
Then, in 2014, he sought help. “I was actually told, ‘You look sick.’” Friends referred him to Headstrong and he’s never turned back — first as a client and now running its day-to-day operations. “That’s when you start to do the work,” says Shryrock. “You address moral injury. Consistent bombardment or enemy fire. You address the absurdity of war. Thanks goodness I cleaned myself up.”