Gesmer Updegrove

Push ‘little pebbles’ aside to accelerate growth

The Shift is a series of interviews by FoundersWire and its partners that explore the issues, challenges and possible solutions that accelerate scale. Our first Q&A features Steve Snyder, partner and entrepreneur-in-residence at Gesmer Updegrove LLP. He meets, above right, with fellow Gesmer colleague Chrissie Lee and Boston design entrepreneur Katie Burkhart. (FoundersWire photo)

FW: You started out not only as a lawyer, but as a tech entrepreneur yourself. What appeals to you now about working with entrepreneurs?

A: Practicing law was never my passion. Building businesses always has been. So the opportunity to meet with two, three or four entrepreneurs every day and help them with their business challenges is extraordinary.

What value do you add that’s unique, beyond the necessary/obvious legal support?

The focus of our firm is working with entrepreneurs to ensure the success of their companies. We focus on the business, not just the law. We provide valuable business advice and guidance as well as legal advice and guidance. In my role, I focus only on business. For me, it’s about finding ways to drive revenue, increase profitability and help entrepreneurs succeed, all at no charge.

You’ve worked with many hundreds of founders and CEOs while they’re scaling. What do you see that they all have in common? What’s one marker that says, yes, this one is going to make it?

That’s a fabulous question. Most of our clients are tech companies so the CEOs with whom I have worked are really smart. That’s a given. The most successful CEOs are thoughtful and considerate; open to advice and guidance; good listeners; truly aware of their areas of strength and want to supplement or complement those areas by building a team around them; and able to process information and make decisions.

What pitfall do you often see that you wish founders were more aware of?

I wish I had been more aware of this early in my career but, as the saying goes, “Hindsight is 20/20.” Scaling a company is really hard. There are hundreds and hundreds of little details that we think about every day. It often feels like we’re being bombarded by little pebbles. It’s those little pebbles that divert our attention from the “big boulders,” the big stuff that we need to focus on to achieve our goals. Push those little pebbles aside, prioritize, delegate, but most importantly, focus on the big boulders.

Building a startup is stressful. Scaling one is even more challenging. What advice can you offer founders to find peace of mind, even after they realize they don’t have all the answers?

Wow, I wish I could offer that kind of advice. The best I can suggest is to surround ourselves with really smart, experienced, thoughtful advisors. That way, we don’t need to have all the answers.

Do you have a lesson you’ve learned while helping entrepreneurs scale that might help others? Let us know. Have a question that Steve might be able to help with? You can reach him directly at

This week’s events for founders and fun

Check out this week’s can’t-miss events in the area. 

Monday, July 25: Business Sustainability Bootcamp, hosted by SkyLab Boston, 6-9 p.m., Bruce C. Bolling Municipal Building, 6th floor, 2300 Washington St., Roxbury. FREE. Register here.

Tuesday, July 26: Finance & Accounting for Startups Post-Investment, hosted by The Capital Network at MassChallenge, 21 Drydock Ave., Boston. 11:45 a.m.-2 p.m. Register here.

Wednesday, July 27: Annual Summer Reception, 5:30-7:30 p.m., members $75, non-members $150, hosted by the Boston Chamber of Commerce in the tent behind the New England Aquarium. Register here.

Green Card & Career Advice Q&A Session for Ph.Ds, 6-8 p.m., hosted by Casseus Law and Propel Careers at the Cambridge Innovation Center, 1 Broadway, 5th floor, Cambridge, $15. Register here.

Startup Showcase, 6-9 p.m., hosted by MassChallenge at the Innovation & Design Building, 21-25 Drydock Ave., Boston. FREE. Register here.

Thursday, July 28: SheStarts Networking Breakfast, 8:30-10 a.m., at WeWork Fort Point, 51 Melcher St., Boston. FREE. Register here.

Regatta for Entrepreneurship, noon-6 p.m., sponsored by The CFO Center, Gesmer Updegrove, FoundersWire, Telamon Insurance and Bowen Advisors, to benefit the Network for Teaching Entrepreneurship. At the Boston Sailing Center, 54 Lewis Wharf, Boston. Network and race for the NFTE Cup. Learn more here.

Hiring in Tech: What companies are really looking for, 6-8 p.m., hosted by ChickTech Boston at WorkBar Cambridge, 45 Prospect St., Cambridge. $10. Free business head shots first come, first served. Register here.

Friday, July 29: The White Party, 6-10 p.m., hosted by Boston Business Women on the patio at Society on High, 99 High St., Boston. $50. Each ticket purchase includes a plus one. Men welcome. Register here.

Do you have an event you want to promote? Let us know here. We choose the best events for our readers and publish every Monday

Sailors heed ocean’s call in Regatta for Entrepreneurship


BOSTON—Some pretty adventurous executives and their teams are getting ready to prove their mettle at the Regatta for Entrepreneurship, kicking off at the Boston Sailing Center at noon on Thursday.

The inaugural regatta, which has already raised more than $70,000 for the Network for Teaching Entrepreneurship, has called some old salts—like Nexxus Group CEO Mark Landgren—back to the water.

“It’s been a long time since I’ve done any competitive racing,” Landgren says. “I got started in sailing in my early 20s. My roommate bought an old Cal 25 and we refurbished it. We were in an old, slow boat but the social and networking aspects were so great. I just didn’t know that was out there.”

That connection—to both sailing and business—is what the regatta aims to bring to Boston growth companies. That’s what makes the regatta especially appealing, Landgren says. “It’s a really unique networking opportunity, being in close proximity to other racers and having some competitive gybes back and forth,” he says.

The start gun goes off at noon for the first fleet of J24s, with the second heat starting approximately two hours later. Teams may choose to deploy their spinnaker down wind, or stick to white sail, which could prove either genius or disastrous in the predicted 5- to 10-knot breeze.

But for those who don’t know their tacks from their clews, it’s all about the crews. “We have multiple opportunities to meet other people and companies, we get to spend a great afternoon out on Boston Harbor with friends and colleagues, and still do something for a great cause.”

NFTE, founded in 1987, provides programs that inspire young people from under-resourced communities to stay in school, to recognize business opportunities and to plan for successful futures.

The long-term benefit to society speaks to the event’s entrepreneur-sailors, who have experienced the advantages of entrepreneurship firsthand, and are making their donations and support for NFTE a team sport. “I used to do a fair bit of networking, but I was usually the only one who got to go,” Landgren says. “This time, I can bring my team, I think that’s the best part,” he says. “I was able to coax my executive team out there with me so we can have a great afternoon on the water.”

The teams of four, plus one skipper assigned by the Boston Sailing Center, have been strategizing for months, working through the maneuvers that will get them across the line in time to hoist the NFTE Cup, a work of art designed and crafted by Long’s Fine Jewelers. And some are just looking forward to competing against other in-market business colleagues.

“A couple of my Vistage friends are on another boat, so we’ll be competing for bragging rights—not for who wins but who doesn’t fall overboard,” Landgren says with a laugh. “It will be interesting because we have experienced skippers but everyone else has to work in tandem to make it work.”

The community has rallied to support this inaugural event, including founding sponsors The CFO Center, Gesmer Updegrove, Telamon Insurance and Bowen Advisors. (FoundersWire is also a founding sponsor.) The shore party, with food, cocktails and live music on the deck at the BSC, will be sponsored by Harbor One Bank, with in-kind sponsors Goslings Rum, HINT Water, Castle Island Brewing Company, Long’s Fine Jewelers, and SYB Events.

Sailing team sponsors include Baker Newman Noyes, Fanzcall, Nexxus Group, OpenView Venture Partners, WaterSuite (Corona) and Vistage.

Individual sailors from the following companies also will attend: 89 Degrees, Alipes, Apptient, AR Funding, Botkeeper, Cantina Consulting, Cogitacorp, CounterTack, East Coast Product, Excellent Writers Group, FE International, Filmmakers’ Collaborative, imac, Insequent, Intengenx, IR+M, M5consulting, Media Vue Systems, New England Finish Systems, Noi Strategies, Novis Capital Group, Origin3M, Pabian & Russell, Supporting Strategies, TPG, Trust Design, UPS, Vivantio, Wealth Impact Partners, Wine Riot and WinterWyman, among others.

Sponsors, donating more than $5,000 worth of raffle prizes, include 12 Meter Charters, Bose, Del Frisco’s Double Eagle Steakhouse, Boston Celtics tickets, New England Patriots tickets and Red Sox tickets, Grill 23 & Bar, Legal Oysteria, Prezza, Row 34, Yvonne’s, Nations Photography, Keurig, Soaring Adventures of America Hot Air Balloons, Vineyard Vines, and Wegman’s.

Besides mingling with Boston’s top growth companies, the Regatta for Entrepreneurship is connecting founders with a cause they can really get behind.

“I’m a lifelong entrepreneur, much to my parents’ chagrin … so I didn’t have a lot of mentoring,” Landgren says. “It’s so important to know people who have been there and done that. (NFTE) really fits in with what I’m passionate about, so this was a really easy yes.”

Landgren, who puts mentoring high on the list of activities he looks forward to, gave his best advice to the students of NFTE: “If you work hard, sure, you’ll make mistakes, but you will succeed.”

There won’t be occasion for many mistakes out on the racing course in the hunt for the NFTE Cup—but Landgren notes it’s still better to be out sailing (even with no experience required) than golfing, a far more typical and predictable networking activity.

“Besides the fact that I’m a miserable golfer,” he laughs, “I would much rather be on the water.”

For more information on the Network for Teaching Entrepreneurship, check it out here.

Regatta for Entrepreneurship sets sail for good

“We cannot direct the wind, but we can adjust the sails.”—Thomas S. Monson

There could not be a better metaphor for entrepreneurship than sailing—uncharted water, unpredictable wind and weather, with only your experience, wits and a certain courage to protect you along your journey.

That’s the inspiration behind the inaugural Regatta for Entrepreneurship, setting sail Thursday, July 28, benefiting the Network for Teaching Entrepreneurship. The event brings together the founders of Boston’s best growth companies to connect with peers and partners, while testing their sea legs on Boston Harbor.

“What we’ve recognized is that scaleups tend not to have the same support as other companies,” says Bill Starr, managing director at The CFO Center and regatta commodore. “Startups are part of an ecosystem. Venture-backed companies are part of a portfolio. Growth companies … their path isolates them, they are all busy building their businesses. This regatta creates a new opportunity to celebrate with other companies like them.”

Steve Snyder, partner and entrepreneur-in-residence with Gesmer Updegrove, has long been known in the Boston tech growth market as a friend and connector for founders who need trusted advice. “This event is all about just three things: strengthening friendships and building lasting value in the Boston tech community, having fun and doing good,” Snyder, also a regatta commodore, says. “Building and strengthening relationships is invaluable. There’s nothing more important.”

The regatta brings together more than 150 members of Boston’s tech community: a tight group of founders, friends and sponsors who support growth and want to encourage more of it. Founding sponsors include Telamon Insurance, Gesmer Updegrove, Bowen Advisors, FoundersWire and The CFO Center. Goslings Rum, a brand synonymous with world-renowned sailing regattas, will sponsor the event. Other local sponsors include Castle Island Brewing Co., Hint Water and more.

Following the race, there will be an awards ceremony and cocktail reception from 5-6 p.m. sponsored by Harbor One Bank, where the winning team will begin its yearlong stewardship (and bragging rights) to the much-anticipated NFTE Cup.

Friendly competition is already building across the fleet of participating sailors. “I am looking forward to being with friends—and hoisting the NFTE Cup,” Steve Snyder says. The cup itself, an enviable work of art, was designed and donated by Long’s Fine Jewelers. The winner will play host to the perpetual trophy in their home or office for one year, and be on hand to present the cup to next year’s winner.

But no trophy is worth more than the gift of knowledge that experienced entrepreneurs bring to the next generation of business builders through the work of NFTE.

“We’re looking forward to getting out on the water, and meeting new people who want to strengthen this community. We can do a lot of good while having a great time,” says John Snyder, president of the employee benefits and human resource consulting practice at Telamon Insurance. “Being able to share this event with people who want to make a difference makes this regatta really special.”

This one-of-a-kind networking and team-building day is raising funds for the Network for Teaching Entrepreneurship, a international nonprofit organization providing programs that inspire young people from under-resourced communities to stay in school, recognize business opportunities and plan for successful futures.

NFTE will use 100 percent of the donations raised to provide their innovative programs to 1,000 students across Greater Boston and Hartford, Conn., through Summer BizCamp and NFTE classes the next school year. NFTE provides programs to 60,000 middle and high school students from under-resourced communities around the world each year.

“Helping students learn how to use that entrepreneurial mind-set helps them forge a successful path for the future,” says Julie Nations, director of NFTE New England and regatta vice commodore.

“(NFTE) definitely gave me what I needed,” says Jennifer LaSala, founder of Jennifer Lee’s Gourmet Bakery and successful graduate of the Chelsea, Mass., NFTE program. “Without (NFTE), I would not have any of this.”

“First of all, they kept me in school. I was going to drop out with a 3.8 GPA, but (NFTE Program Manager) Jennifer Green and the teachers, they kept me in,” she says. “They taught me something I could take away from school: How to start a business and everything I would need. You don’t need a lot of money, you just need the ambition to go out and get it.”

The event will set off at noon, with a shore party including lunch, libations and live music at the Boston Sailing Center on Lewis Wharf, Boston. The competition, in round robin format, pits 26 J24s with crews of five plus a skipper from the BSC against each other. There’s no previous sailing experience required.

“I’m really looking forward to watching people who have never sailed before develop a new spirit of camaraderie, not only with their own crew but with other crews that are racing, that’s true Corinthian racing,” Starr says.

Each team sponsoring a boat receives a keepsake burgee (battle flag) with their company logo to fly during the race, plus dri-fit shirts, swag bags and tickets to the regatta party for their crew.

“There are plenty of events at the big end of town, and plenty for startups. This is the premiere, exclusive event for scaleups as they get to share their success with others like them,” Starr says.

Donations and sponsorships are tax deductible. Sponsorships and boats are limited, but still available. Find more information or sign up for The Regatta for Entrepreneurship HERE

Boston growth experts open Gateway to success at global conference

From left, John Snyder, Telamon Insurance; client Jeremy Ellis, Keysoft Solutions; Bill Starr, The CFO Center; Bob Croak, Baker Newman Noyes; and Steve Snyder, Gesmer Updegrove.


BIRMINGHAM, England—Setting up shop in the United States is easier when you work with friends.

To make that more possible for clients, The CFO Centre Group is importing an expert team from Boston for its global conference here.

The group will give a behind-the-scenes look into doing business in the United States, a service The CFO Centre offers global clients through its Gateway to the United States process.

Bill Starr, managing director of The CFO Center New England, will accompany other top service providers here to share their insight with CFOs from around the world. The group includes Steve Snyder, partner and entrepreneur-in-residence at law firm Gesmer Updegrove; Bob Croak, CPA and principal with accounting firm Baker Newman Noyes; and John Snyder, president, Telamon Insurance.

“Our Gateway to the U.S., delivered by Bill and his wider team in Boston, has helped our U.K. clients who wish to start up there enormously,” says Sara Daw, CEO of The CFO Centre Group. “Speaking from our own experience of setting up overseas, it’s key to get a soft landing from friends in town who will help you navigate through everything new, so you get the right advice at the right time and the right price.”

Starr says he faced the same issues that he and his friends now solve for Gateway clients. “When we launched our own U.S. operations, I went looking for the top service providers I could work with, who I knew I could rely on,” he says. “I interviewed a number of different firms and eventually settled on the team that we have now, because they were continually recommended by others in the Boston ecosystem. They were the best, bar none.”

Boston appeals to U.K. companies “because we can relate to it and it’s easy access from the U.K. The technology focus is also a draw,” says Daw.

Boston’s growth is no secret: It was ranked the No. 1 startup hub out of 25 in the United States, according to a May 2016 report by the U.S. Chamber of Commerce Foundation and startup accelerator 1776.

The city earned top billing for its clear advantages: next-generation tech companies specializing in education, energy and health care, high quality of life ratings and a business-friendly regulatory ecosystem, according to a release from the U.S. Chamber of Commerce.

“We’ve seen Boston growing because we’ve been part of it, as business advisors and entrepreneurs ourselves,” says Starr.

Gateway works on a wider scale for global clients looking to start up in the United States, says Daw, because it addresses the unknown with solid answers from people with local experience. “This is a huge opportunity for growth, yet the complexity and unfamiliar ways of doing business and remote working need to be managed. Gateway does just that, enabling growth whilst maintaining control.”

Starr says multiple service providers working in the best interest of a mutual client help mitigate a lot of apprehension. “The chairman of a U.K. company recently told me, ‘We’ve received a lot of conflicting advice from (various U.S. and U.K.) service providers. We get a lot of comfort from the way that you validate each other’s information.’ ”

“We are offering something extraordinary,” says Steve Snyder, who brings nearly 20 years of business growth and legal expertise to Gateway clients. “My starting point is that service providers are a commodity. But at what point do those services become so special that we become indispensable? That’s what we have built here: Together we are a group of trusted business advisors—not just lawyers or accountants, insurance people or CFOs. It’s about being trusted.”

Croak, whose focus is tax, attributes the success of the group to that same trust. “It’s the trust, and the talent that is brought to the table. It’s the process that we bring to these young companies forming into the U.S. and the ability to work off each other. If I find something Steve, Bill or John need to know, it’s an easy phone call.”

Working to create a cohesive strategy across financial, legal and insurance needs is of vital importance, to help companies avoid costly mistakes, Croak says. The Gateway process keeps lines of communication open.

“Because we work on so many clients together, I know when Bill zigs, I can zag,” Croak says. “I can almost anticipate his questions before he even asks. And he has been there with me, to ask the questions but then get my thoughts. Because Bill is the center point of the relationship in most cases, my job is to support him and to make sure we’re getting everything done correctly so there are no problems in the future.”

John Snyder, whose insurance expertise helps clients navigate the multi-layered territory of healthcare, human resources and corporate liability coverage, says Gateway minimizes the risk for them as service providers, too.

“If we know Bob Croak is in there, I can trust his work. It provides a layer of confidence, peace of mind,” he says. “We all ask, ‘Who do you work with legally, or on your finances?’ If we don’t know these (other service providers) and issues come up, it slows our ability to help the client. Because we have such a close working relationship, we know what they’re doing and everything becomes much all more streamlined.”

Gateway’s goal is to simplify the process and keep that door to the U.S. market wide open, John Snyder says.

“It’s challenging enough for domestic companies that have a great idea to run a company,” he says. “When you’re coming from another country, it’s exponentially more difficult when you don’t know the rules and the people. So for (global companies), we have a turnkey solution that can help build a foundation for them. This is where they’re going to take their business to the next level.”

And the work is as satisfying for the Gateway providers as it is for their clients.

“When you work with people like Bill, John and Steve, we just have fun—it’s not work any more,” says Croak. “And the issues that different companies have, we can solve them as a team. Here at BNN, Telemon, Gesmer, CFO Center, there hasn’t been a problem we haven’t been able to solve and that’s fun. It’s fun to get compliments from your clients.”

Meet the first Female founders of the week: SheStarts

Female Founder of the Week (FFoW) is a weekly celebration of the women who are building business in Boston. With this feature, FoundersWire acknowledges the challenges that are unique to women, hails the successes they achieve, and encourages those coming next, so they may learn from these exceptional, undeterred women founders.

SheStarts co-founders, above from left, Nancy Cremins and Liz O’Donnell, have been chosen for the inaugural feature, because not only are they female founders in their own right, they’ve dedicated their resources to being two of the most inspired and powerful advocates this community of female founders could have.


BOSTON—Meeting the right person at the right time can turn a ripple into a tsunami. Using that logic, SheStarts co-founders Liz O’Donnell and Nancy Cremins are about to turn the tide for women building business in Boston.

“We met over Twitter,” said Cremins in an interview over lunch with FoundersWire. “We were both at an event, and I was live tweeting, and she messaged me, ‘hey, are you here?’ And then we finally met.”

When they did, it was obvious they had big work to accomplish together: the first initiative being SheStarts, a group that “supports the growing pipeline of women founders in Boston,” since its first event in 2014.

It’s definitely an undertaking that has a strong market mandate, with more than 130 people showing what Cremins called “some level of support” on their recently successful Kickstarter campaign, raising more than $15,000 to reach their goal.

What is their goal, exactly?

“We’re here to bust gender bias,” said Cremins simply.

“I think of busting gender bias as the top of a pyramid. And then we say, OK, how do we get there,” continued O’Donnell. She listed events, programming and education, and access to capital as the third piece.

“Then, it’s ‘How can we help sustain and grow? That’s the big issue. We look at the social programming that’s gone on, and we think, until you change the frame of reference, it (bias) doesn’t change,” she said.

The pain they’re addressing has been part of the unspoken startup life for women for more than a decade, with the rise in female founders and women-run startups hitting an all-time high. More than 200 startups with women at the helm have been cataloged in Boston, with countless more building in anonymity. But the fact is that few actually get funded. A 2014 Babson study concluded that fewer than 3 percent of venture-supported companies had a female founder. This same study, however, showed that businesses with women on the executive team were more likely to have higher valuations.

“The idea that it’s a meritocracy, it’s complete and total nonsense,” Cremins said.

“ ‘I’m willing to fund women, but I just don’t find any,’ ” O’Donnell intoned, pretending to be a male investor. “Call it swagger, but there’s a double bind. (As a woman), come in tooting your own horn, and you get knocked down.”

Being different and looking different from the groups you’re pitching, Cremins pointed out: “The very process creates a sense of anxiety,” she said. “The rules of the game weren’t written for you, so you have to navigate a very narrow path.”

“But it relates to: How do we step up to this without alienating men? You invite them in,” O’Donnell said.

The two are perfectly in sync, able to finish each other’s sentences, anecdotes and manifestos. They also share a spectrum of life experience and professional expertise: Cremins is a litigator with tech-focused law firm Gesmer Updegrove, who applies her prowess to solving employment issues and intellectual property disputes, and especially to supporting women-run startups. She is also a longtime board member of the Women’s Bar Association. O’Donnell is an author with a long list of published works, best known for “Mogul, Mom & Maid: The Balancing Act of the Modern Woman.” She’s simultaneously developing a social movement addressing the phenomenon of being a “Working Daughter,” balancing life amid the work and challenges of caring for an elderly or failing parent.

“I realized you have to take the lead,” O’Donnell said. “You can’t just talk about why there are no women leaders. You have to stand up. You can’t just write about it and preach about it, when you’re not doing anything about it.”

She gave an example of the female founder’s gambit, illustrating the stereotypical roles women play, and how they create unique challenges for entrepreneurs: “You’re a good daughter, good student, good worker. You take all the notes, clean up the parties, work through all the details. You’re a good wife, a good mother.

“Then you shift to being a founder, and it’s hard to break that mold,” she said.

In Boston, Cremins said, being a female entrepreneur should be an advantage by now.

“Why fit in when you were meant to stand out?”

Shelagh Braley is the editor of FoundersWire. Follow her @FoundersWire on Twitter. FoundersWire is actively seeking submissions for Female Founders of the Week to profile. Please share with any you know, and send inquiries to

Angels: Your network is everything


BOSTON—If you’re an entrepreneur, some days are easy. And then there are days when you could really use an angel.

Meeting some was as simple as attending Gesmer Updegrove’s angel funding event at WeWork South Station Wednesday night. The panel met an audience of more than 100 attendees, the bulk of whom (by show of hands) had teams of at least two, as well as working products.

“Not too many had revenues, but there were certainly some,” Gesmer partner Bill Contente said in an interview. “Most had taken in friends and family money, but only a handful had angel or VC money. They were exactly the people who needed this information.”


Gesmer’s Lynne Riquelme, far right, welcomes the panel of angel investors: (from left) Christopher Mirabile, Joe DeMartino, Barbara Clarke and Catherine White, with moderator and Gesmer partner Bill Contente.

Contente led the evening’s conversation, designed to deepen understanding of the investment process—something he said requires a lot of nurturing. “We have lots of incubators and collaborative work spaces popping up all over Boston. Bringing the people around who actually invest, to teach new companies what (angels are) looking for is something we thought was a good way to keep them on good trajectories,” he said.

Catherine White of Golden Seeds said working with angels should fundamentally bring value. “Of the different angel groups, and I’ve counted 31, you have to decide which one is going to be the most helpful. Do the research on them but try not to make too many assumptions. If they just want to talk: ‘Back in 1930, you know what I did…’ ” she joked, “that’s probably not the right angel.

“You want someone who wants to work with you the way you want to work,” she said. “And you should ask them how they think they would like to work with you. You need to ask yourself: Is it worth putting up with what I’m getting.”

But make that assessment early—before any money is exchanged. “Often we say taking angel money is like getting married but you can’t get divorced. We have a stake in your success,” said entrepreneur-turned-investor Barbara Clarke of Astia.

“Ideally they’ve had a few startups of their own, have seen success, and in large part want to give back,” said Joe DeMartino, managing director and head of deal flow for the Angel Investor Forum. “You want people who are willing to give you advice and have the expertise that will help you. An introduction goes a long way.”

But please don’t try selling angels on your product. They far prefer to know about you. “What criteria do we use to evaluate? The single most important thing is the team, the founder. And we look for coachability, someone who is willing to listen, someone that isn’t a know-it-all,” said Christopher Mirabile of Launchpad Venture Group.


“You have to understand, it’s a different message than you tell your customers. It’s a sales process so understand what we are looking for. It’s team, market and product. For me, that’s the order, product comes third,” DeMartino said.

“Start very early to have a diverse team. You’ll make better decisions and you’ll be a better company. Research shows companies with women on the team do better. Don’t waste time being a monoculture company,” Clarke said.

But don’t expect funding before you’re ready—which generally starts with staying rooted in reality and finding customers.

“Do a sanity check on your model,” Mirabile said. “Benchmark the key assumptions in your model.”

Of course, money you’re booking speaks louder than any other signs of readiness. “If you’ve got a working prototype or software beta, nothing says success quite as loudly as the reality of revenues,” White said. “We’re like, wow, you actually have customers and it’s not your aunt and uncle?” she joked to the laughing audience. “We really like to see that.”

“You need to get into the heads of the people sitting up here,” Clarke said. “Try to see the world through their eyes. You have to see what they’re seeing in order to figure out how to get to a yes. You should never go into these meetings clueless. A fellow entrepreneur will be happy to tell you what’s it like. What are they into?”

“VCs invest about $25 to $35 billion a year in businesses,” Mirabile said. “A lot of people are surprised to find out that the angel market is roughly the same size, about $20 to $25 billion a year. VCs make about 5,000 deals a year. Angels make about 70,000.”

Angel investment is up across the country, according to the Angel Resource Institute’s Q3 report for 2015, with median round sizes more than doubling since 2014. The report also showed New England coming in second on the list of regions to invest the most angel capital, at 15.5 percent. California tops that list at 19.7 percent.

Would that margin of investment—or any investment—be reason enough to move west? According to Mirabile, just the specter of funding isn’t enough, because raising money is about tapping into personal connections.

“If you really don’t care where you live and you have a line on money, then go ahead and move. But you have to know your personal network is going to be more valuable than an entire metropolitan area,” he said.

“I think it’s pretty much possible to get any kind of business funded anywhere. You ask the three questions: ‘What do you think?’ (of my company, product, etc.), ‘Is there anyone I should talk to?’ and ‘Would you be willing to introduce me?’ That is easier to do where you know some folks,” he said.

He went on to address the draw of Silicon Valley. “There are very young angels with a lot of money around, in their 20s and 30s. Sure. The flip side is it’s brutal to find talent, the cost of living is high, and really, there’s just a lot of hype going on,” Mirabile said.

“For my money, Boston is the best place in the country to build a company.”

The panelists offered a warning, too: “Beware the fake angels,” Clarke said. “They like the lifestyle but don’t really like to actually invest a lot of money. You have to know the difference,” she cautioned.

DeMartino said the best way to source out an angel’s validity is to come right out and ask. “Ask them how many investments they’ve made, and what kind of companies they’ve invested in.”

“Every time!” said Clarke. “And you shouldn’t be buying them coffee.”

The next event in the Gesmer Updegrove Fundraising Series, featuring insight on venture capital, will be held April 6. Follow @gesmer on Twitter for more information.


Above board: SheStarts experts on choosing advisors


BOSTON—As a founder, where do you turn when you need advice? If you’re truly innovating, there isn’t a single source—often you have to collect expertise from multiple sources to patch together a plan. If you’re lucky, those handpicked experts can become your advisory board, according to the SheStarts panelists who shared their thoughts Monday night.

Christopher Mirabile of Launchpad Venture Group, entrepreneurs Joyce Lonergan (CEO and co-founder of Mellitus LLC) and Helen Adeosun (CEO and founder of Care Academy) joined serial entrepreneur/moderator Tina Weber at WeWork South Station to share advice on choosing an advisory board. Here are the 5Ws you should know, plus a little extra:

SheStarts co-founder Nancy Cremins introduces the panelists at Building and Using an Advisory Board.

SheStarts co-founder Nancy Cremins introduces the panelists at Building and Using an Advisory Board.

WHO should be an advisor:

“Your advisory board is a group you’ve collected who are focused on helping you,” said Mirabile. “It’s people you can rely on … an industry expert, someone who might be in your slide deck. That’s on the more formal name-dropping spectrum.”

“They’re supposed to make your load lighter. You don’t want to bring on anyone that will make more work for you,” Lonergan said.

WHAT is the best way to work with an advisor:

“You say, ‘Here’s what I’m thinking, does that work for you?’ Then put them to work, give them homework, let them know that’s what you expect. Calling them up, saying ‘What do I do?’ is not the way to go, to give them confidence in you as a leader. Be explicit about whether they’re OK with you using their name, and make sure they know your story,” Mirabile said.

“There has to be enough connection, you don’t want to be forgotten. Each call has to be a transaction. And then ask yourself, ‘Did I get what I needed?’ It’s up to me to bring them along, their time is valuable,” Lonergan said.

“It happens organically. We like each other and how each other thinks,” said Weber. “Just don’t question yourself too much. Lay it out there, lay out your ideas.”

“Call them, but not to the point where it keeps you from moving your company forward. If I ask a question and they come back asking, ‘How did that go,” I latch on. It doesn’t have to feel so boisterous and sales-y. See who is really into it,” Adeosun said.

WHEN should you choose an advisor:

“If you need advice, you’re ready,” said Mirabile. “Do it as soon as you can use one.”

“If you need advice, you’re ready,” said Mirabile. “Do it as soon as you can use one.”

“You listen better if you create something first, and you get better feedback,” said Adeosun. “(One of my advisors) picked apart my crap like I don’t know what, but it was great. She’s now a valuable member of my advisory.”

WHERE can you find qualified advisors:

“I ask myself all the time, ‘Who do I know who does that? Sometimes it comes from LinkedIn, who does my group know? Through partnering and outside vendors, I’m always trying to find a thread of commonality,” said Lonergan.

“A lot of times I’m already working with someone, and they say, ‘Do you mind if I list you (on my slide deck).’ It starts out with networking, asking for advice, and good chemistry. (The entrepreneur says:) I’m picking your brain, you give me good answers, and then say, would you like to take this to the next level,” Mirabile said.

WHY choose to work with an advisory board:

“We are showing our customers, these are the people advising us every day, we’re being pushed forward,” said Adeosun. “And it keeps you accountable, right? You don’t want to mess up those relationships, so you work even harder.”

HOW should you work out compensation:

“As an entrepreneur, I never have enough money or time. I try to do everything as low cost as possible. But I’ve learned not to skimp when I need smarts,” Lonergan said. “If you can get the magic of your idea across, sometimes you can get them to help beyond a paycheck.”

“If you can get the magic of your idea across, sometimes you can get them to help beyond a paycheck.”

“If they’re putting in a ton of time, making intros or lending you a name with the halo of recognition, that could be a quarter of a percent to half,” said Mirabile, “or in exceptional circumstance, up to 1 percent of common stock options.”

Mirabile had special advice about this, and also covers it in his blog, “You can outgrow expertise early, so give them less (stock) maybe, but let it vest early so they aren’t hanging around when you don’t need them. Shoot for less stock and faster vesting.”

Adeosun referred to a resource that she has found valuable, a founder/advisor standard template: “The Founders Institute lays out the process by experience and cache, setting expectations, this work is worth x-amount.”

Best traits to look for in a quality advisor:

CM: Availability, willingness to help and super-networked is a key feature. A lot of people are hard to schedule with, they give you shallow answers.

JL: Master of their craft, give you great depth of answers, and trust is so important, for what I ask to be held in confidence and not twisted.

HA: Their ability to connect and work with people in our industry. Whenever I consider an advisor, I ask in passing, ‘What do you think of this person?’ People admire them for how much they are willing to give, and I look at how much people love them within the industry.

And Nancy Cremins, SheStarts co-founder and attorney with Gesmer Updegrove gave the final word: “When you do put together your advisory, make sure everyone doesn’t look the same or you won’t get that good diversity of thought.”

Good advice across the board.