Successful serial entrepreneurs share their most valuable advice

In 2017, the “entrepreneurial bug” is prolific. For those bitten by it, there is nothing more invigorating than the seed of a successful business idea.

But in our startup-saturated society, with an abundance of businesses that promise to disrupt everything from the daily commute to dental floss, the truth is that only a small percentage of companies ultimately make the cut. When it comes down to it, entrepreneurship is hard — and reaching the upper echelons of success requires a serendipitous cocktail of dedication, passion, people, and sometimes, a little bit of plain luck.

The right advice is key, too. There’s no better source of wisdom than those who have navigated the stormy seas of entrepreneurship and emerged victorious on the other side — especially if they’ve managed to do it not just once, but repeatedly. We spoke to several such serial entrepreneurs on the Sunday Times Hiscox Tech Track 100 list (read their success stories here) to get their top tips. Below are the key takeaways for budding entrepreneurs.

Passion is fundamental

Nearly every entrepreneur who spoke to Mashable emphasized the importance of passion. When taking the leap into the great unknown, having a strong belief in your idea is an absolute must.

Clive Jackson, an entrepreneur who has built 14 companies over the course of his entrepreneurial career, agrees that  fervour is fundamental. Often, deep-seated passion is what separates the wannabes from the success stories.

“When you set out down the path to be an entrepreneur, do not think you’re setting out to make millions and look great amongst your peers … it isn’t about you showing off. It’s a long and painful process, and the demands upon you are enormous. Be very genuinely passionate about why you’re doing it, and about wanting to create something. That’s the first hurdle,” he says.

Marc Biles, an entrepreneur who has assisted in the launch of a total of 16 businesses, says entrepreneurs need to be prepared to embrace words like “relentless” and “obsessed.”

“If you’re going to launch your own business, it’s going to be really hard work. You’re going to spend more time working on it and thinking about it and living and breathing it than you will on anything else,” he says. “You’re going to forget friends’ birthdays, you’re going to turn up late to family get-togethers, you’re going to stare at your email whilst you should be listening to the story your partner is telling you on date night. If you’re going to dedicate yourself on that level to something, you need to really love it,” he says.

Stress test vigorously

Jackson attributes many entrepreneurial misfires to a lack of critical stress testing —  burgeoning entrepreneurs need to poke holes in their concept and go to great lengths to consider every possible competitive threat.

“Once you’ve got an idea, a concept, a vision and you think it sounds great — you think to yourself, “Why wouldn’t somebody do this?” — once you have modeled it out, and you’ve articulated and documented it, then turn it on its head. Ask, why would somebody do this?” he suggests.

Hand in hand with stress testing, new entrepreneurs must avoid developing blinders when it comes to a concept’s feasibility and potential for scale.

“People don’t size the market properly, they don’t go out there and do the research, they don’t genuinely look at the competitive threats that are out there,” says Jackson. “There may only be 45,000 people in the world who this [idea] would appeal to.”

To mitigate this skewed sense of optimism, Jackson says entrepreneurs need to meticulously scrutinize their closest 10 competitors or potential competitors.

“Genuinely write a paper with an introspective reflection about how you would undo your great new startup,” says Jackson. “So many people think that their idea is so good and so different, but they never really stress their value proposition to the point as to whether it is defendable. So they tend to get carried about with how many people will bite.” This, he explains, leads to bewilderment when entrepreneurs sit down in front of a group of investors who point out obvious flaws and vulnerabilities in the business plan.

Richard Theo, an entrepreneur who has been at the helm of six businesses throughout his career, adds that it’s important to test your idea on real people — not just friends and family. “Friends and family will always just give you the ‘X Factor answer’ — i.e. they’ll tell you you’re a great singer, even if it’s painfully evident that you’re not,” he says.

Know your numbers, and know when to seek outside help

Thanks to the internet, podcasts, and a plethora of print material about building businesses from the ground up, there are innumerable resources out there for would-be entrepreneurs.

So, says Biles, it’s shocking how many people dive off the deep end without conducting proper due diligence. “It’s amazing how many businesspeople I meet who could tell me how much Neymar’s transfer fee was when he was sold from Barcelona FC to PSG — but couldn’t tell me what their conversion rate by source is or how their attrition rate over time is changing, etc.,” he says.

Dana Tobak, a renowned broadband entrepreneur, reiterates that hard numbers are the yin to the yang of “gut feeling.”

“Knowing the potential full cost of your decisions is important,” she says. “Don’t assume you’ve properly forecasted all your costs and customers. What happens if the price of your biggest input goes up? What happens if it takes double the time to bring a product live? You may not need to plan for the worst circumstances, but you need to understand the full range of potential outcomes.”

Being intimately acquainted with your startup’s metrics and pain points, too, will help when it comes time to seek funding.

“I think for early-stage growth companies, it’s key to understand when and where to bring in financing,” says Jackson. “Victor, my 14th company, is the first one where I’ve brought in external funding, and I’ve scaled faster and quicker than any of my peers in the private jet charter space by leaps and bounds.”

Jackson also says that recognizing when to be flexible and when to be “encompassing” is another key piece of the puzzle.

Don’t constrain yourself with a ‘small shopkeeper’ mentality.

“Don’t constrain yourself with a ‘small shopkeeper’ mentality because you want to control the shop and be in charge of everything and do it all your own way,” he says. “There’s nothing wrong with wanting this; but fundamentally, if you’re going to attract sophisticated investors, they need to be able to see that you’re not so dogmatic in your views that you can’t see the woods for the trees.”

This, Jackson recognizes, is perhaps the most paradoxical element of entrepreneurship: Founders must be passionate — practically to a fault — yet still willing to relinquish control and accept external input.

“You have to drive through with a huge amount of tenacity, but in the same breath, constantly look back and be very reflective about what you do,” he says. “You have to constantly ask, ‘Can it be done any better?'”

Think long and hard about elements of company culture

Giles Palmer, founder and CEO of social listening platform BrandWatch, paints the picture of the ideal entrepreneurial Venn diagram: “Figure out how to be in the crosshairs of resiliency, compassion, and hard-work,” Palmer says. “Those for me are the three most important characteristics of successful entrepreneurship. You get the ups and downs… there’s one step back, three-quarters of a step forward, two steps back, three steps forward … it’s just an ongoing journey.”

Palmer emphasizes the importance of compassion in the workplace. “As you work with other people, you need to care,” he says. At his company, for example, he has turned compassion into a concrete values system that defines the company culture. Truth, authenticity, accountability, and connectedness also make the list.

At Tobak’s company, Hyperoptic, she says she takes an approach of “active management” to ensure strong culture and continuous growth.

“It’s conscious decision-making,” she says. “Don’t let things just ‘happen’ — make conscious decisions about your people, your products, and your processes. Agree on priorities — some things will have to wait, others can’t — and make sure everyone on your leadership team agrees.”

Biles adds his two cents to the point of compassionate culture: “Be generous. Be generous with your time, be generous to your customers, be nice to people generally and good things will happen to you,” he says.

The entrepreneurial journey certainly has its ups and downs — but listening to the advice of those who have forged their own path provides a valuable foundation for success. With the right people by your side, a sense of perseverance, a passion for your product, and a pinch of luck, you can set yourself up for the best possible chance of prosperity.


This Startup Teaches Domestic Violence Survivors To Be Entrepreneurs

There are a lot of reasons why domestic violence victims find it difficult to leave their abusive partners.  Financial concerns are often one of the largest.  The abusive partner may prevent the other person from working, or may control their wages and bank accounts or credit cards, so survivors of domestic violence often need to start over financially.

“For a lot of victims, they leave with almost nothing,” says Carolann Peterson, PhD, who teaches courses on domestic violence as an adjunct professor at the University of Southern California Dworak-Peck School of Social Work. “Many times they don’t have any control of the funds within an abusive household.”

To help survivors support themselves (and often their children), domestic violence organization FreeFrom provides entrepreneurship training to survivors. The pilot program launched in May in Los Angeles and in June in Oakland and San Francisco with the first cohort of 30 women (80% of whom are mothers).

Similar to how a startup incubator helps entrepreneurs, participants receive pro bono legal advice, mentoring, marketing advice, and logo and website help through partnerships with organizations including Kiva, Mission Asset Fund, Centro Community Partners, Bet Tzedek, Start Small Think, and others. The weekly classroom portion lasts six months, but the survivors have access to those resources more informally after that.

So far, three-quarters of participants have either launched their business or they’re in the prelaunch stage, and all of them make a profit in their first month of business. They’re almost entirely B2C businesses building on survivors’ existing skills, including a cleaning service, hair styling, catering, and jewelry design.

Most importantly: None of the survivors have returned to their abuser.

A participant who started a handmade greeting card company while living in a shelter (for safety and privacy reasons, we’re not identifying survivors by name) says the program helped her with “picking a name, a business email, a logo, legal advice, setting up goals, and even making a plan around my finances.” She was unsure about launching a business from a shelter with a limited budget but says FreeFrom helped her tackle things step-by-step. “My finances are getting better and will continue to get better as my business grows,” she adds.

Another participant says learning about different legal structures for businesses was one of the most valuable parts of FreeFrom’s entrepreneurship program. “This idea became so real when I chose what type of structure my business will be, and when I got to talk to a lawyer about it,” says the participant, who chose sole proprietorship for her mobile hair-braiding company.

In addition to the formalized entrepreneur cohorts at FreeFrom, Peterson says some groups of survivors form business co-ops among themselves. For instance, they might start a cleaning service together and take turns cleaning homes or watching each other’s kids.

Peterson says survivors who get support in launching a business, even if it’s from peers, are often poised for success despite the financial and emotional challenges their situation poses. “Those are survivors who not only go on to have productive lives, they go on to help others,” she says. “They have the ability to be productive as role models for their kids.”

CEO Sonya Passi

CEO Sonya Passi, who holds a JD degree from the University of California, Berkeley, launched FreeFrom in November of last year. The organization also offers a credit-building program, and Passi felt entrepreneurship would also help survivors build confidence and get on firmer financial footing.

“Survivors have a really hard time getting regular employment,” Passi says. There are a number of reasons for this. “It’s taking too many sick days because of your injuries, an abuser coming to work and causing a scene, and you losing your job as the result of that, having to flee and having to leave behind your home and your community and your job,” she explains. 

”Often survivors don’t have much in the way of a resume, and if they do, it’s very scattered,” Passi says. “As we’re thinking about how survivors can rebuild, often traditional employment isn’t obtainable.” When a survivor does leave an abuser, they may not have access to childcare, which can also make it challenging to hold down a regular job. But they could perhaps make jewelry or provide seamstress services, as some of the survivors in this cohort are doing.

Passi feels that while the more flexible requirements of entrepreneurship fit survivors’ needs, their resilience and resourcefulness also makes them ideally suited to start a business. “In order to survive abuse like that, you have to have those skills, and these are the skills that are required to succeed in business,” she says.

Still, survivors of domestic violence may face challenges that most other entrepreneurs don’t: privacy and safety. While many entrepreneurs share details of their lives and build their personal brands on YouTube, Snapchat, and Facebook, survivors may have very real concerns about their abuser tracking them down, so they’ll often set up a business that doesn’t use their own name.

“The answer for a lot of our clients is having a business that doesn’t require them to put their face and their personal details online, and build it in a way that is fairly anonymous,” Passi says.

To address the safety concerns of meeting new clients, some participants use Tannia Ventura, FreeFrom’s entrepreneurship program manager, as their check-in buddy. If they’re anxious trusting new people, they’ll text Ventura when they meet with a new client, and when they’re done. “That helps me feel so much safer, and I appreciate that,” says the owner of the mobile hair-braiding company.

While these survivors may not share their names, they do share their stories of survival and resilience. “What’s so extraordinary is they want to own their survivorship,” Passi says. “So much of what our society does is it shames you for being a victim of domestic violence.” Many of these entrepreneurs show solidarity with other survivors by building community into their business model. For instance, Passi says, a survivor might say that for every essential oil kit they sell, they’ll give one to a survivor in a shelter.

FreeFrom plans to serve up to 60 clients in each city next year, and expanding its Bay Area reach to include Contra Costa County and East Palo Alto. The organization is also working with the NYC Mayor’s Office to Combat Domestic Violence to bring its program to New York City in 2018.


Startup Weekend Latinx in Tech Winners in Oakland Pitch Tech Solution to Help Puerto Rico and Mexico Relief Efforts

54-hour Event Part of National Effort to Increase Latinx Talent in Tech

1st place team, Las Casitas (pictured above), was made up of students from Chabot Community College and UC Berkeley

Oakland, CA (October 2, 2017) – This weekend, the Kapor Center for Social Impact, Techqueria and Techstars hosted Startup Weekend Latinx in Tech: Oakland. The event was part of a national effort to bring visibility, access and exposure to aspiring Latinx entrepreneurs across the U.S. Three more simultaneous events took place in Los Angeles, Chicago and New York.

Startup Weekend, a Techstars program backed by Google for Entrepreneurs, is a 54-hour team competition in which participants design, build and pitch their startup ideas to a panel of venture capitalists and seasoned entrepreneurs.

The winner of the final pitch competition was a team called Las Casitas. Using tech to create sturdy building materials from recycled plastic, Las Casitas pitched to build affordable, environmentally-friendly housing that could withstand natural disasters and contribute to relief efforts in the aftermath of Hurricane Maria in Puerto Rico and the earthquakes in Mexico. The team was made up of students from Chabot Community College and University of California, Berkeley.

Second place winner, a team of formerly undocumented Latinx entrepreneurs, sought to simplify the immigration process using chatbots.  My Little Piñata, a company that celebrates culture through a customizable miniature piñatas online platform, and Camisetas, an online subscription-based t-shirt service that supports manufacturers that pay living wages, tied for third place.

The event brought together a diverse group of Latinx and ally college-aged students and young adults with technical and non-technical backgrounds from across the Bay Area. Throughout the weekend, professionals from the local tech, startup and venture capital communities volunteered their time to coach and mentor participants in preparation for their pitches.

said Lilibeth Gangas, Chief Tech Community Officer at the Kapor Center for Social Impact.

There was a total of 10 teams that pitched their startup ideas to a panel of judges that included Freada Kapor Klein, Partner at Kapor Capital and Kapor Center for Social Impact, Miriam Rivera, Managing Partner at Ulu Ventures and Shauntel Poulson, General Partner at Reach Capital. Teams focused on creating startups with a positive social impact that tackled social, economic and political barriers faced by Latinx communities. Other startup concepts included:


  • Using blockchain technology to circumvent predatory lending in low-income communities
  • Reducing the college drop-rate through a mobile mentorship platform experience
  • Bridging the gap for students in the Central Valley through a life skill-based curriculum
  • Teaching computer science through video game learning with culturally relevant content


First place winners Las Casitas received the grand prize of 6 months incubation at the Kapor Center Innovation Lab (iLab) which includes workspace, mentorship and office hours with Oakland Startup Network & Kapor Capital.

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