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Sukhinder Singh Cassidy’s CEO journey – TechCrunch

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After listening to others pitch me a few different job opportunities while still at Google in 2008, it became clear to me that I would make a better decision if I could fully explore the larger landscape of new companies emerging in Silicon Valley.

I had spent the last several years focusing on Google’s business outside the U.S., and I honestly felt out of touch with the startup world. Beyond my goal of becoming a CEO of my own company, I had two other ambitions: I wanted to help build a great consumer service that would delight people (potentially in e-commerce) and I wanted to build further wealth for myself and my family.

To better evaluate my options, I made the decision to quit Google first and find a way to study the wider ecosystem of companies before choosing where to go. Resolved to give myself a “blank slate” before making a final choice, I left Google when I was three months pregnant and joined Accel Partners, a top Silicon Valley venture capital firm and an investor in my previous startup, in a temporary role as CEO-in-residence.

In the months that followed, I helped Accel evaluate investment opportunities across a wide variety of digital sectors, with a particular focus on e-commerce, taking the opportunity to study those companies I might join or think of starting from scratch.


On Thursday, August 19 at 2 p.m. PDT/5 p.m. EDT/9 p.m. UTC

Managing Editor Danny Crichton will interview Sukhinder Singh Cassidy, author of “Choose Possibility,” on Twitter Spaces.


One of Accel’s key partners, Theresia Gouw, helped me brainstorm, joining my cadre of professional priests. We had known one another for over a decade (I originally met her as a young founder at Yodlee) and were at similar stages of our careers, so I knew she could identify personally with my career quandaries. Like me, Theresia was pregnant with her next child and at a similar life stage — yet another commonality.

Image Credits: Sukhinder Singh Cassidy

While at Accel, I spent a disproportionate amount of time testing my macro thesis that online shopping was about to explode in new ways. I had seen the rise of e-tailers at Google (many of these companies, such as eBay and Amazon, were Google’s largest advertisers at the time), but many of the leading e-commerce sites like Amazon and Zappos still had a utilitarian feel to them.

Meanwhile, new fashion and décor e-commerce sites such as Rent the Runway, Gilt, Houzz, Wayfair and One Kings Lane were popping up everywhere and growing rapidly. These sites sought to tap into a more aspirational and entertainment-oriented kind of shopping experience and move it online.

Expert investors like Accel and others were funding them, and my own observations suggested that this area would yield another big wave of online consumer growth. These lifestyle categories of shopping also appealed to me personally; I was the target customer for many of them.

I started to work on an idea for a new e-commerce service, a luxury version of eBay, while listening to the pitches of every e-commerce company that was looking for funding and talking to several that needed early-stage CEOs. I continued to listen to non-e-commerce pitches as well, simply to give myself a point of reference for evaluating online shopping opportunities.

At Yodlee and Google, I had been lucky enough to work with incredibly smart and talented people who shared my values, and I wanted to do the same at my next venture.

I wanted to work with great investors, too, and fortunately I had the ability either to work with Accel-funded companies, start my own or leverage other investor relationships I’d developed. I spent time with multiple company founders to try to discern who they were as leaders, in addition to what they were working on.

By this point in my career, I had a pretty clear idea of my own superpowers and values, so I looked to find companies that could make the most of my unique gifts and whose founders or senior leaders had strengths complementary to mine.

Specifically, I hoped to join a company with a very strong engineering and product management culture that needed a CEO with strategy, vision, business development, fundraising and team-building expertise. Applying these criteria, I turned down several opportunities at companies whose founders had skill sets too similar to mine, reasoning that this overlap might lead to conflict if I ever became CEO.

Finally, I used my time at Accel to think long and hard about the risks I would take in becoming a startup CEO and whether I could afford to fail. My biggest risk by far was ego- and reputation-related. Mindful of how precarious early-stage startups are, I feared that I would leave a successful role as a global executive only to suffer a very large and visible failure. But the more I thought about this, I faced this ego risk head-on and concluded that my reputation as an executive from Google would hopefully be strong enough to survive one failure if it came to that.

The personal risks of taking on a startup CEO role felt different but not greater than those associated with my job at Google. While I knew that serving as a first-time CEO while having another newborn at home (my son Kieran) would be immensely stressful, I would likely benefit from no longer traveling around the world for days and weeks on end and working across multiple time zones, as I had previously.

Last, I evaluated the financial risks of potential moves. Although my startup equity would have uncertain value for a long time, I judged this a risk worth taking, given how excited I’d feel to have more impact and responsibility as CEO. While I lost a large financial package in choosing to leave Google and switching to a startup salary, I could pay the bills at home while digging into my savings only slightly. Under these conditions, I was prepared to make the leap.

In early 2010, almost a year after I left Google, I finally found the right opportunity and decided to join fashion technology startup Polyvore as its full-time CEO. A precursor to Pinterest, Polyvore was based on the idea that women could “clip” online images to create fashion and décor idea boards digitally that were instantly “shoppable.”

Millions of young women (including influencers) were already using the service and loved it. The founding team was led by a rock star engineer, Pasha Sadri, along with three other product and technology folks he recruited from the likes of Yahoo and Google.

Pasha was known for his intelligence, and we had connected informally over the years for coffee, each time having great discussions about business strategy. In fact, Polyvore twice before had tried to recruit me to become its CEO, once when I was at Google and again when I departed that company in 2008. Back then, I’d spent a productive afternoon with the founding team, helping them think through their business model. I also knew Peter Fenton, one of Silicon Valley’s most successful investors and a leading funder of the company. Peter was the one who first introduced me to Polyvore and who continued afterward to passively court me.

Having spent so much time exploring my options from multiple angles, I was now poised to make a great decision. I felt convinced that e-commerce was starting its next wave of growth, and felt excited to be part of it.

Within that vision, Polyvore was among the companies best positioned to succeed, and I knew I could contribute in significant ways to building a service that would delight millions. I was impressed with the strengths of Polyvore’s founder and investors and anticipated that I would be able to complement their efforts nicely. Recognizing that my success as a startup CEO hinged on my relationships with the founder and board, I had also invested time to get to know them.

Meanwhile, I had faced my fear demons, taking financial risk but negotiating my offer aggressively to account for downside scenarios I imagined, and coming to grips with my ego risk. With all this work in place, I finally jumped.

After managing a multibillion-dollar profit and loss and leading a 2,000-person team at Google, I became the newly minted CEO of a 10-person fashion startup in February 2010.

As we tee up the bigger choices in our careers, we all face critical moments of decision. No choice we make will be perfect, and all the frameworks in the world won’t eliminate risk entirely. But we don’t need perfection or freedom from risk. We just need to take the next step.

By choosing thoughtfully, using all the tools at our disposal to maximize our upside and anticipate our downside, we can grasp the opportunities available to us while equipping ourselves to handle whatever challenges reality throws our way.

Excerpted from “Choose Possibility: Take Risks and Thrive (Even When You Fail)’ by Sukhinder Singh Cassidy. Copyright © 2021 by Sukhinder Singh Cassidy. Published and reprinted by permission of Mariner Books/Houghton Mifflin Harcourt. All rights reserved.



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Bolt to expand EV option in South Africa – TechCrunch

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Estonian on-demand transport firm Bolt is set to roll out electric taxi options in South Africa four months after introducing e-bike food delivery services in the country.

Bolt’s plan follows the introduction of a ‘green category’ – which lets riders hail an electric or a hybrid vehicle. This comes as the company expands its services to environmentally friendly modes of transport.

“We are looking to roll out a green taxi category in South Africa in the next few months, and plan to roll out green categories in other African markets,” said Bolt’s regional director for Africa and Middle East, Paddy Partridge.

The company already offers a green option in Kenya, where it also runs e-bike food delivery. It also plans to launch e-mobility options for food delivery in its other markets across East Africa, including Uganda and Tanzania. 

Founded in 2013 by Markus Villig, the tech firm, which has operations in 45 countries – including seven in Africa – runs a gamut of services comprising ride-hailing, car, scooter and bike rentals, food delivery, and recently grocery delivery, fashioning itself as a transport and deliveries company.

“In East Africa we see a lot of potential on the motorbike side, and especially for delivery. We plan to invest more in this direction as it also serves to eliminate the challenges associated with constantly fluctuating fuel prices, currently the most significant operating cost for our couriers,” said Partridge.

Opportunities for electric mobility are said to be huge, but a majority of countries lack the necessary infrastructure to support their adoption, says a UNEP report

A lack of recharging infrastructure, low grid power connectivity, and generally expensive e-vehicles remain hindrances to the adoption of electric transportation options in many African countries. 

A transition to electric power would offer countries in sub-Saharan Africa a range of gains, including affordable transport and a reduction in emissions, with fossil-fuel vehicles contributing 12% of the region’s total emissions, according to the SSA Nature Sustainability report.

Bolt is planning arrangements with banking institutions in its markets in Africa to help its drivers access credit for purchasing electric vehicles, exploring other options away from its current scheme with leasing companies.

“The purchase cost and import duties are often high, thereby deterring ownership. We are exploring a number of vehicle financing partnerships in Kenya and South Africa for electric cars and bikes, which would help make it easier for drivers to get access to, and eventually own, electric vehicles,” he said.

The company’s plan to expand its offering across the continent comes in the wake of growing competition from companies such as Uber, which is currently testing a carpooling service in Nairobi, with plans to roll it out in Ghana and Nigeria.

Bolt recently launched the food delivery service in Nigeria, and also expanded its reach in South Africa by rolling out the service in Johannesburg after introducing it in Cape Town last year.

This comes in the wake of the company’s recent $696 million (€600M) funding round that the tech firm said will go into growing the new grocery delivery service, Bolt Market, as well as in expanding its other transport and delivery services. 

Sequoia Capital, Tekne Capital, and Ghisallo, G Squared, D1 Capital, and Naya Capital are some of the investors that participated in the funding round that increased its valuation to €4 billion. The new funding came after the International Finance Corporation injected $24 million (€20) into the business at the beginning of the year.

Among the services it is looking to grow is Bolt Drive, the car rental service launched early this year to offer different choices including compact, mid-size, electric, premium, SUV, and van. The service is currently available in Estonia’s capital Tallin with plans to roll it out in other Europe and Africa markets. Bolt Drive adds to the micro-mobility options – scooters and e-bikes – that the company introduced in line with its goal of availing to the masses, more budget environmentally friendly transport solutions. The e-mobility service is available in over 100 cities across Europe.

“We continue to scale up our operations for the benefit of our customers.  Our core business is to provide reliable, safe and affordable transportation services to everyone and we are excited to make travel easier and quicker in many cities across the continent,” said Partridge.



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“Pikmin Bloom,” an AR mobile game, is Niantic’s next collaboration with Nintendo – TechCrunch

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Niantic announced yesterday that its next augmented reality mobile game will be Pikmin Bloom, a collaboration with Nintendo. The free game is available now for iOS and Android in Singapore and Australia, but will roll out globally in the coming days.

Like Pokémon Go, Pikmin Bloom will encourage players to get outside and explore their neighborhoods. Only now, instead of catching Pidgey and Rattata, you’ll collect seedlings and create a squad of Pikmin. The more you walk, the more Pikmin you’ll collect. These plant-animal hybrid creatures come from Nintendo’s strategy and puzzle game franchise of the same name.

Pikmin Bloom marks the sixth installment in the Pikmin video game series. There are many different types of Pikmin to interact with, and as you walk alongside them, you’ll leave augmented reality trails of flowers behind you. According to in-game footage in the announcement video (seen above), it looks like you can customize your avatar as a Mii.

Another feature that borrows from Pokémon Go is Pikmin Bloom’s monthly Community Day events. In the former, players are lured outdoors with special bonuses and rare featured Pokémon once per month, encouraging people to get outside and befriend fellow players. Niantic hasn’t released details, but the company said that it will host monthly Community Day events for Pikmin as well to plant and play together.

Pokémon Go has a weekly pop-up on Monday mornings that shows you how far you’ve walked that week. But Pikmin seems more specifically geared toward encouraging movement, showing the routes you walked and the steps you took at the end of every day.

The last time the two companies released a game together, it shattered expectations — so, no pressure to our floral friends. Even if Pokémon Go doesn’t feel as ubiquitous as it did in summer 2016, it’s making Niantic more money than ever, netting over $1 billion in 2020. But it doesn’t quite seem like there’s as much to do yet in Pikmin Bloom as there is in Pokémon Go or Harry Potter: Wizards Unite. So, this game might be geared toward a more casual crowd who just want to see some pretty pixels while they walk — no shiny-hunting and raid battle coordination here…at least not yet.



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QOA brings in seed round to do for chocolate what Oatly did for milk – TechCrunch

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Munich-based QOA is gearing up to be among the first to bring a chocolate product to market that is 100% cocoa free.

It is also now backed by $6 million in seed funding in an investment round led by Cherry Ventures with participation by 50years, World Fund, Nucleus Capital, Trellis Road, Pioneer Fund and Tet Ventures.

The company kicked off this year, founded by the sister-and-brother team of Drs. Sara and Maximilian Marquart. Sara Marquart is a food chemist with a specialty in flavor formation, while Max Marquart is a material scientist and now three-time entrepreneur.

QOA, chocolate

QOA’s product test kit

The global chocolate confectionery industry was valued at over $208 billion in 2020, and is the largest part of the industry in the U.S. Two-thirds of the world’s cocoa supply comes from West Africa, but is at risk — one of the reasons the Marquarts decided to focus on it. Currently, up to 50% of the current cocoa supply is at risk due to pathogens and climate change, and cocoa is playing a role in both deforestation and forced child labor.

“Our food supply is threatened due to the way we eat,” Max Marquart told TechCrunch. “We love chocolate, however, we realized that there are some sustainability risks and wanted to do something about it so we can still have it in the future.”

Companies, like California Cultured and Voyager Foods, are also creating chocolate without the cocoa using different approaches. Meanwhile, QOA developed a fermentation process that uses natural byproducts from other food-making processes for its base material. It then uses proprietary microbactera and flavor formation to create a vegan product that mimics the texture and flavor of chocolate, but without any artificial additives, he said.

The fermentation process will enable the company to scale production by 2035 and be able to price its products the same or below the cost of traditional chocolate. In fact, Marquart is predicting that in the future, the chocolate market will have two pillars: one half that is exclusive, expensive products made with normal cocoa, and the other QOA products.

QOA was part of Y Combinator this year and was able to get its product test kit going so people can sample nine options. Marquart expects to have QOA’s first product on the market in 2022, and the new funding will go toward building out its first pilot production facility in Munich to complement one it has in Switzerland and hiring.

The company is in talks with its first business-to-business customers and expects to close some smaller contracts soon, Marquart  said.

“After that, we will go after our Series A so we can build out larger production lines,” he added.



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How to root out shadow IT and maximize SaaS investments – TechCrunch

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Growing reliance on SaaS has opened the door to shadow IT: SaaS applications bought by individual employees without the knowledge or approval of their organization’s IT department.

While shadow IT can be an opportunity for innovation, if left unaddressed, it can lead to risks like duplicate subscriptions, wasted IT spend, a lack of compliance and greater risk of a data breach.

By leveraging SaaS management and taking some steps, businesses can more effectively manage shadow IT, gain a competitive edge, reduce unnecessary costs and empower a distributed workforce.

To avoid the negative consequences associated with shadow IT, you need to give IT teams visibility into your organization’s entire SaaS portfolio. Once IT has a line of sight into all applications in use and how they are used, they are positioned to optimize investments. Maximize your SaaS investments with these tips:

Implementing self-service SaaS at your organization is easier than you may think.

Discover all SaaS applications and spending

Some organizations take a spreadsheet-based approach to managing their SaaS applications. Others turn to web browser plugins, single sign-on tools and cloud access security brokers. But these discovery processes can be time-consuming and involve piecing together SaaS inventories from disparate sources, often resulting in records that are out of date before they’re even completed.

Even the most detailed, frequently updated spreadsheet is not always the most effective way to manage SaaS, especially when you consider that organizations manage over 650 SaaS applications on average, and they underestimate the number of SaaS applications within their ecosystem by two to three times. If you don’t know a SaaS application exists, how can you manage and budget for it?

To optimize your SaaS portfolio, you have to start with gaining complete visibility. Tools like SaaS management platforms with machine learning capabilities that detect SaaS purchases enable continuous discovery of software. These solutions can also integrate with your financial management systems to discover purchases.

It’s critical for this strategy to happen in real time so you have a picture of your tech ecosystem that’s always complete, accurate and up to date.

Optimize and rightsize licenses and features

Do you have as many active users as you accounted for or could you downgrade your plan? Perhaps an employee left, but their accounts were never deactivated. In practice, you may not need all the premium features or seats you’ve paid for, which means there could be opportunities to reduce your SaaS spend.



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Apple launches Fitness+ group workouts powered by SharePlay – TechCrunch

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Apple has launched a new way for Fitness+ users to work out or meditate with people in other locations through group workouts powered by SharePlay. The tech giant first teased the feature at its September 14th virtual event.

Fitness+ subscribers can use SharePlay to start a group workout or meditation session with up to 32 other people while using FaceTime on an iPhone or iPad. The Fitness+ session will stream completely in sync for everyone on the call.

To begin a group session, users need to start a FaceTime call and navigate to the Fitness+ app. From there, you can select a workout and get started. SharePlay also works with Apple TV so users can follow the workout on a larger screen while staying connected with their friends on FaceTime through their iPhone or iPad.

Apple notes that when you work out in a group through SharePlay, you’ll see their metrics and progress toward closing their Activity rings. When someone closes their Activity rings during a workout, everyone in the session will be notified.

Additionally, Fitness+ will be available in 15 new countries on November 3rd, including Austria, Brazil, Colombia, France, Germany, Indonesia, Italy, Malaysia, Mexico, Portugal, Russia, Saudi Arabia, Spain, Switzerland, and the United Arab Emirates. Fitness+ will be available in English, with subtitles in Brazilian Portuguese, English, French, German, Italian, Russian, and Spanish.

The service is currently available in the U.S., Canada, Ireland, New Zealand, Australia and the U.K. With this upcoming expansion, Fitness+ will be available in 21 countries in total.

Apple also says that ​​beginning November 1, 2021, around 3 million fully insured UnitedHealthcare members in the U.S. will be able to enroll with Apple Fitness+ for a year-long subscription, at no additional cost as part of their plan benefits.

Fitness+ is also introducing a new episode of its Time to Walk series, which is an immersive audio walking experience, with actor and disability advocate Marilee Talkington. In this episode, she talks about defying expectations and how she helps empower others to do the same.

Apple launched Fitness+ on December 14, 2021, and has since worked to compete with other subscription fitness offerings, including Peloton. Fitness+ is available as a standalone subscription for $9.99 per month, or as a part of the Apple One Premier plan for $29.95 per month, which gives users access to Apple Music, Apple TV+, Apple Arcade, Apple News+, and iCloud+ with 2TB of storage.



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Marcy Venture Partners, cofounded by Jay-Z, just closed its second fund with $325 million – TechCrunch

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Marcy Venture Partners, the venture firm cofounded in 2018 by Shawn Carter (Jay-Z), former Roc Nation CEO Jay Brown, and former Walden VC general partner Larry Marcus, says it has closed its second fund with $325 million in capital commitments. The team, which closed its debut fund with $85 million, is now managing $600 million in assets altogether, says cofounder Marcus.

The firm describes itself as having a “consumer, culture and positive impact” investment strategy, and it says the majority of its existing portfolio companies are founded or run by people who identify as women or people of color.

To date, the trio has written checks to at least 21 companies, including in fashion, skin care, and food companies. Among those many bets includes Rihanna’s lingerie company Savage X Fenty; the sneaker marketplace StockX; Therabody, which makes percussion therapy tools; Simulate, which makes plant-based, chicken-flavored nuggets; and an allergen-free cookie maker called Partake Foods.

Carter and company have also begun investing in crypto projects, supporting Bitski, a San Francisco-based startup NFT marketplace, earlier this year, and investing more recently in spatial LABS (sLABS), a tech incubator that focuses on the metaverse and blockchain-based products

The San Francisco- and L.A.-based firm, named after the Marcy Projects in Brooklyn where Carter grew up, was initially targeting $200 million for the newest fund, per an SEC filing from April.



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Heart to Heart raises $750K to bring sweet, sweet flirtation to your ear-holes – TechCrunch

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Radio has long been described as the most intimate of media. Quips about putting radio on the internet aside, the persistent popularity of podcasting and the cockamamie climb of Clubhouse shows that audio-based platforms will continue to echo around the upper echelons of the ecosystem for a while yet. Joining the fray is Heart to Heart, an audio-first dating app aiming to bring back some intimacy to the process of finding the right person for your next foray, whether that’s a saucy encounter or a mate for life.

“I used to act, and from my time in acting, I saw how much voice, and audio experiences drive intimacy between people,” explains Joshua Ogundu, co-founder and CEO of Heart to Heart. “When it came down to the dating apps, it was never something I could get into. I felt like you needed to come up with a textual one-liner. That was never my way of approaching romantic conversations.”

Heart to Heart is pushing back against the endless swiping and messaging of many of its competitors, offering a contrasting experience to sending the same opening line to dozens of people or typing with your thumbs until deep into the night.

“I believe that the best consumer investments come from people who have unique insights on consumer behavior and ways that new tech products can allow new forms of social interaction,” said Charles Hudson from Precursor Ventures, who led the pre-seed investment round. “I have been a big fan of Josh’s TikTok videos for some time and his ability to poke at the tech industry with timely, relevant videos really showcased his creativity and ability to communicate via short-form video. I think the idea around confirming photos, storytelling, and audio will yield a product that really speaks to people’s unmet needs around communication and will create a whole new way for people to connect.”

While Precursor doesn’t particularly focus on audio-first startups, the team has seen a number of opportunities in that space. It was an early investor in Howard Akumiah’s company, Betty Labs (acquired by Spotify), as well as Isa Watson’s company (Squad), Falon Fatemi’s company (Fireside) and several others that are still in stealth.

“I believe that there is a major wave of interesting activity happening around non-music audio and I believe that we are still in the early innings of non-music, audio-driven social experiences,” says Hudson. “The last two companies that I feel really innovated in this category were Tinder and Bumble. I think Josh and his team have a new mechanic that feels differentiated and unique and I think it has the potential to be the foundation for a new way for people to meet and get to know each other in ways that aren’t easily accomplished today.”

Joshua Ogundu, co-founder and CEO of Heart to Heart (Photo provided by Heart to Heart)

The company raised the pre-seed round of $750,000. The round was led by Precursor Ventures, and Bryce Roberts of OATV & Angelica Nwandu of The Shade Room partnered on the investment, as well as Marie Rocha at Realist Ventures. In addition, a number of angel investors joined the round, including Chris Bennett (Wonderschool), Andy Weissman (USV) and Gregory Levey (Robinson Huntly).

“The main thing we are trying to accomplish with the $750K, is to focus on building our iOS app, and making LA our first launch market,” says Ogundu. “Dating is such a local experience, and it makes sense to us to build and improve locally, then scaling it up from there.”

“Voice is so intentional and intimate, and that is exactly what we’re building here at Heart to Heart,” says Ogundu, suggesting that the voice mechanic is helpful in a dating context because it helps slow people down. “I think that because it takes more energy to send that voice snippet to someone, you’ll be more intentional with who you even look to strike up conversations with.”

The founding team consists of Joshua Ogundu, who wears the CEO hat. He is joined by Arihant Jain and Komal Shrivastava, who have been heading up the engineering and design efforts. The company hopes to get its product to market by the end of the year.



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