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To measure sales efficiency, SaaS startups should use the 4×2

01:33 | 7 December

Brian Ascher Contributor
Brian Ascher is a partner at Venrock, where he invests broadly across enterprise and fintech and serves on the boards of several companies, including Personal Capital, 6Sense, Socrates AI, Dynamic Signal, Retail Solutions, SmartBiz Loans, and Inrix.

Once you’ve found product/market fit, scaling a SaaS business is all about honing go-to-market efficiency.

Many extremely helpful metrics and analytics have been developed to provide instrumentation for this journey: LTV (lifetime value of a customer), CAC (customer acquisition cost), Magic Number and SaaS Quick Ratio are all very valuable tools. But the challenge in using derived metrics such as these is that there are often many assumptions, simplifications and sampling choices that need to go into these calculations, thus leaving the door open to skewed results.

For example, when your company has only been selling for a year or two, it is extremely hard to know your true lifetime customer value. For starters, how do you know the right length of a “lifetime?”

Taking one divided by your annual dollar churn rate is quite imperfect, especially if all or most of your customers have not yet reached their first renewal decision. How much account expansion is reasonable to assume if you only have limited evidence?

LTV is most helpful if based on gross margin, not revenue, but gross margins are often skewed initially. When there are only a few customers to service, cost of goods sold (COGS) can appear artificially low because the true costs to serve have not yet been tracked as distinct cost centers as most of your team members wear multiple hats and pitch in ad hoc.

Likewise, metrics derived from sales and marketing costs, such as CAC and Magic Number, can also require many subjective assumptions. When it’s just founders selling, how much of their time and overhead do you put into sales costs? Did you include all sales-related travel, event marketing and PR costs? I can’t tell you the number of times entrepreneurs have touted having a near-zero CAC when they are just starting out and have only handfuls of customers — which were mostly sold by the founder or are “friendly” relationships.

Even if you think you have nearly zero CAC today, you should expect dramatically rising sales costs once professional sellers, marketers, managers, and programs are put in place as you scale.

One alternative to using derived metrics is to examine raw data, which is less prone to assumptions and subjectivity. The problem is how to do this efficiently and without losing the forest for the trees. The best tool I have encountered for measuring sales efficiency is called the 4×2 (that’s “four by two”) which I credit to Steve Walske, one of the master strategists of software sales, and the former CEO of PTC, a company renowned for its sales effectiveness and sales culture. [Here’s a podcast I did with Steve on How to Build a Sales Team.]

The 4×2 is a color-coded chart where each row is an individual seller on your team and the columns are their quarterly performance shown as dollars sold. [See a 4×2 chart example below].

Sales are usually measured as net new ARR, which includes new accounts and existing account expansions net of contraction, but you can also use new TCV (total contract value), depending on which number your team most focuses. In addition to sales dollars, the percentage of quarterly quota attainment is shown. The name 4×2 comes from the time frame shown: trailing four quarters, the current quarter, and the next quarter.

Color-coding the cells turns this tool from a dense table of numbers into a powerful data visualization. Thresholds for the heatmap can be determined according to your own needs and culture. For example, green can be 80% of quota attainment or above, yellow can be 60% to 79% of quota, and red can be anything below 60%.

Examining individual seller performance in every board meeting or deck is a terrific way to quickly answer many important questions, especially early on as you try to figure out your true position on the Sales Learning Curve. Publishing such leaderboards for your Board to see also tends to motivate your sales people, who are usually highly competitive and appreciate public recognition for a job well done, and likewise loathe to fall short of their targets in a public setting.

4x2 chart venrock saas

A sample 4×2 chart.

Some questions the 4×2 can answer:

Overall performance and quota targets

How are you doing against your sales plan? Lots of red is obviously bad, while lots of green is good. But all green may mean that quotas are being set too low. Raising quotas even by a small increment for each seller quickly compounds to yield big difference as you scale, so having evidence to help you adjust your targets can be powerful. A reasonable assumption would be annual quota for a given rep set at 4 to 5 times their on-target earnings potential.



The inevitable takedown of the female CEO

00:30 | 7 December

Sara Mauskopf Contributor
Sara Mauskopf is the CEO and co-founder of Winnie, a marketplace for daycare and preschool helping over 4 million parents across the U.S. Prior to founding Winnie, Sara held product leadership roles at Postmates, Twitter, YouTube and Google.

Four years ago when I founded Winnie, I set out to build a different kind of startup. Above and beyond any success our business achieved, it was most important to me that we create a culture where people would want to work. As a new mom at the time, I intentionally decided to build a company where employees would not work on nights or weekends, where there was flexibility for employees to manage their lives outside of the office, where motherhood would no longer be a penalty but a bonus and where underrepresented groups would be valued and promoted. If we failed because we did those things, so be it.

Four years later, I’m proud of the culture my co-founder Anne Halsall and I have built. As it turns out, treating employees well, valuing their families and personal time and diversifying our team are not only the right things to do, but also competitive advantages.

Even so, I worry that being a woman and taking on the role of co-founder and CEO places a target on my back.

Aggressive. Blunt. Furious. These are words that have been used to criticize the behavior of female CEOs of prominent companies like Thinx, Cleo, Rent the Runway and ThirdLove, to name a few. Away is the latest female-led company to come under fire, in an article in The Verge on Thursday.

First, let me be clear: A toxic work culture is never acceptable. Regardless of who started a company or what kind of stress the company is under, it’s never okay to mistreat employees. Some of the things that came to light in these pieces are particularly abhorrent: sexual harassment, lying about one’s credentials, creating an unsafe space for underrepresented groups, overworking employees. These are dynamics that need to be called out and eliminated at all companies, whether female or male-led. The Away example is no exception.

But as a female founder and CEO of a growing company, I have to ask: Why does it seem like so many of the toxic companies in the news are founded and led by women? The number of major public corporations led by female CEOs is less than 5%, and of the 134 U.S.-based unicorns, only 14 even have a woman with a co-founder title.

For such a small fraction of female-led companies, the amount of negative press female CEOs receive is glaringly disproportionate. I have a couple of ideas why.

First, while much of what is revealed in these reports is disgusting, what also comes through is the stereotype of women leaders as “bitches.” Articles often highlight when female CEOs curse, yell and show anger or bawdiness, because the shock value is higher than when male CEOs demonstrate these behaviors. We ask women leaders not only to be successful, but also to be ladylike and likable. I have lost count of the number of times I’ve been criticized for not being warm and friendly enough, or saying things that were too blunt.

Second, studies show that when it comes to ethical failures, women are “judged more harshly than men.” The ThirdLove article calls out that “at a by women, for women company” ThirdLove’s practice of discouraging salary negotiation was particularly disappointing. Cleo’s last-minute setup of a mother’s room using hanging curtains and a TaskRabbit was described by employees as one of the “more outrageous” behaviors of the founder. As a breastfeeding mom myself, I hate when mother’s rooms are inadequate, but male-led companies have poor lactation accommodations all the time.

The way we are targeting female founders and CEOs is doing nothing to encourage gender equality. It is only ensuring that the number of female CEOs is dwindling under the pressure of having to live up to stricter standards than men. So what can each of us do to create a more fair and accurate picture?

Reporters should continue to hold companies accountable, but just seek stories of male CEOs in equal proportion to the number of male-led companies out there. Those stories are there and only a few of the very worst examples have been exposed. Let’s have it take much less time to expose the next Travis Kalanick or Adam Neumann.

As readers, it is also worth being aware of our own biases. We can ask ourselves if we’re more outraged at a behavior because it comes from a woman, and if there are men we’re allowing to go unscrutinized. We can ask ourselves if maybe we enjoy seeing successful women taken down a notch (I certainly hope the answer is no).

I will continue to implement a healthy work environment at Winnie, grow a company where my employees can thrive and hold myself to the highest standards of conduct. But as we continue to take down the already few female CEOs one by one, I can only hope that what I do will be enough.



Will the 2020s be online advertising’s holistic decade?

00:04 | 7 December

Todd Dipaola Contributor
Todd Dipaola founded inMarket to bring the performance and accountability of digital advertising to offline brands.

With less than two months left in the decade, advertising is again entering a new phase of rapid expansion with customer experience front and center.

The explosion of data and identity management, combined with technical advancements in real-time signal detection and machine learning, present new opportunities to respond to consumers, but mastering this ability enables marketers to create “magic moments” — instances of hyper-relevant content, delivered at the perfect time and place. 

We’ll see evolutions on the back end in terms of delivery and measurement — as well as on the consumer-facing end — through new creative deployments that enhance the brick-and-mortar shopping trip. Marketers will be held to a higher standard, both by clients demanding world-class performance and proof, as well as consumers who want relevancy, helpfulness and privacy from their brand relationships. 

Achieving this balance won’t be an easy task, but the most progressive marketers will succeed in driving this industry toward a more customer-centric future because they took steps to evolve before it was too late. With that in mind, here are five ways we expect advertising to become more holistic in the 2020s: 

Smart data will take priority over big data

Most marketers have heard the adage, “garbage in, garbage out.” For too long, the industry relied on sheer quantity of data with no quality metrics for making key audience assumptions. This mentality has had a detrimental effect on our industry, creating an ecosystem where people simply hate ads and brands focus on viewability over ROI.

To truly understand our audiences, we must first turn data from multi-channel interactions into smart, actionable insights. This involves not only understanding who the customer is, but what motivates them. 

Progressive marketers will continue to invest heavily in identity graphs to tie critical data and behaviors to individual profiles across channels. Using data science and machine learning, marketers will then be able to advance their knowledge about consumers to new levels, employing new messaging tactics based not only on value, but also on what inspires action. Key nuances, like distinguishing a deal-seeker from a value-seeker, will lead to more engaging personalized experiences and ultimately better ROI for advertisers.

We’ll see a flurry of investment in real-time engagement

We live in a world where our technology predicts where we are going, what we are seeking and how long it will take to get there by recognizing our patterns and everyday behaviors. The benefits in terms of convenience and knowledge are addictive. Look no further than email, social and Alexa to see how real-time awareness and time savings from these interactions impact our everyday lives.  

For marketers, capturing this lightning in a bottle has always been elusive — until now. The rise of real-time advertising, customer data platforms (CDPs), data science and machine learning have created the ability to detect purchases as well as online and real world location signals in real-time. This enables marketers to not only predict the next shopping trip, but what a consumer is likely to buy, when it matters most.

These sense-and-respond capabilities will enable progressive marketers to create experiences of enormous value at the moments that matter, such as triggering an offer of relevance upon entering a store or delivering a tailored experience at a specific time and location. The new decade will bring about massive investments into these technologies given their immediate ability to influence consumers during the actual purchase process. We’ll see budgets being specifically carved out to support real-time advertising and technologies as marketers optimize and convert users with greater effectiveness.  

For consumers, it means that the in-store experience will continue to become more interactive, with mobile devices as the connecting point between e-commerce and brick and mortar. Brands that thrive in this environment will win by delivering meaningful creative that connects both online and offline worlds in a helpful and relevant way.

Cutting-edge tech will create new ad experiences



Raising VC in Silicon Valley as a female POC

23:26 | 6 December

Nathan Beckord Contributor
Nathan Beckord is CEO of, a software platform for raising capital and managing investors that has helped entrepreneurs raise over $2 billion since 2016. He is also the host of Foundersuite’s How I Raised It podcast.

As the world grows increasingly digital, the craving for face-to-face connections is surging. Squad, an invite-only community and app, is trying to fill the need for offline connections by curating tight-knit events for Gen Z and Millennials.

“It mimics building relationships in real life,” says founder and CEO Isa Watson.

It’s an idea that investors are already backing: Squad closed a $3.5 million seed round and plans to raise its Series A in early 2020, but the road to securing that round was anything but easy. During a conversation on the How I Raised It podcast, Watson shared the ups and downs of her unique path to fundraising.

Establish credibility for a few years before fundraising

She started by putting some of the earliest capital into the business herself with support from her family. She then worked her way through more than 200 meetings in Silicon Valley to build up her credibility as a founder — a step that she can’t stress enough — before Squad even started its official seed round.

“Despite the fact that I went to MIT, despite the fact that I managed a billion-dollar product at JPMorgan Chase and even built a huge digital product, I was still a Silicon Valley outsider,” Watson says.

People sometimes have the perception that being an alumni at a top U.S. university will mean they can go to Silicon Valley and just be “in,” Watson explains, but that’s not quite how it works.

“It takes a lot of work and a lot of credibility building,” she says. “That’s what I was doing for a few years before we actually did our official seed round. By the time I did it, it was like my reputation preceded me and there was enough familiarity with me.”

isa watson squad ceo

Isa Watson, Squad founder and CEO

Don’t do the cold outreach thing — warm introductions only

Despite taking more than 200 meetings in her efforts to crack Silicon Valley, Watson never took a cold meeting.

“Cold outreach is a tactic that I see a lot of founders using,” she says, “whereas I would argue that the more effective introduction comes from someone who knows someone.”

Leveraging the connections she built was critical in connecting Watson to her eventual funders. “They’re all referring you to the next three people to talk to,” Watson says. “It becomes like tree branches and then a network that’s growing in a multiplicative fashion.”

One of Squad’s earliest investors was Steven Aldrich, who at the time was working as chief product officer at GoDaddy . Both Aldrich and Watson grew up in North Carolina, and Steven’s father shared hometown roots with her, which helped her make the initial connection.

“It was about consistently making connections like that,” she says. “Steven introduced me to three people, and then those three other people introduced me to two people. And that’s essentially how I got the ball rolling.”

Not all meetings need to be about meeting for coffees or lunches, either — Watson took plenty of calls while expanding her network, as well. But the important step was making those connections, which was “a really hard hustle and grind, head down,” for the first two years.

Be really specific when asking for advice

When meeting people in Silicon Valley or expanding her network of prospective funders, Watson didn’t tease future funding rounds or send off vague meeting requests.

In trying to build out her network, she first researched a couple of key things: who did she need to know in order to build a really strong product, and who did she need to know in order to have solid distribution or growth marketing? Once she identified those folks, she would reach out to them individually and ask them for specific advice in their area of expertise.

“People always say, ‘When you want money, ask for advice. If you want advice, ask for money,’” Watson says. “Being super-explicit in the ask and explaining how you’ll spend their time and their brain space is super important.” No one has time for a generic request like, “Hey, can I pick your brain?”

When you’ve connected with someone, you should always ask them for recommendations for experts in specific areas — like growth marketing, product, etc. If they volunteer a few names, ask if you can send an email that they could forward on to introduce you to those individuals.

Following the introductions, it’s important to remember that it’s not just a “one and done,” as she says. Once you’ve met with someone through an introduction, follow up: let them know how the meetings went and thank them again.

“It’s like really, really intense relationship management, and it’s something that people with the highest EQ do best,” says Watson. “I would identify my needs, make specific asks … and then I would make sure to explicitly ask if they did not offer for three other intros for people that could be helpful, that would be excited about what we’re doing.”

Secret weapon: your fundraising quarterback

When she realized it was time to start raising money for Squad, her first move was to identify her “quarterback for fundraising” — in this case, Charles Hudson from Precursor Ventures. It’s helpful, according to Watson, to not have “too many cooks in the kitchen,” or else you’ll end up with far too many opinions that don’t align.

Hudson had already invested a small amount of money in Squad at the time, but he quickly became the person Watson went to for feedback on her pitches. He counseled her on other aspects of running a process.

“One thing Charles tells me is that, with fundraising, you’re likely only going to be successful if that’s your core focus at that time,” Watson says. “It’s not something you can do passively.”

So Hudson and Watson sat down and came up with a list of 35 target venture capitalists. He introduced her to five who she didn’t expect to be a good fit. They first went with the ones they didn’t expect would be a perfect match so she could gather feedback and see if Squad was actually ready to raise capital.

Of those first five meetings, one or two “were complete dings” and turned Squad down outright — but Watson made it to partner meetings in the three other meetings, a sign that VCs were seriously considering Squad.

Based on that feedback, Hudson introduced Watson to 10 more VCs — and shortly after, she met Michael Dearing at Harrison Metal, who led Squad’s seed round.

Choose your seed funders carefully

After Dearing offered up a term sheet of $3 million, Watson quickly had offers from other VCs.

“It’s funny because it took me deliberately being in the market for fundraising for like two and a half months to get that ‘yes’ from Michael. Before that, I had no cash really committed,” she says. “And then after just a few days of letting people know I had a term sheet for $3 million, I had like $6 million on a table. VCs are such followers.”

With that many offers on the table following Dearing’s lead, Watson was in the enviable position of needing to pick who she’d let into the seed round. So how did she choose?

“The first thing is value add,” Watson says. She asked herself: “did I feel like I had the right assortment of value? I maybe want someone in there who’s really short on product; I may want someone who’s really strong at growth, strong at marketing.”

Her second criteria for making the decision was a less resume-focused. Simply put, she went with her gut.

“One thing that founders really, really underestimate is — is this person a good human being? I went with the people that I had felt most comfortable with, the people who I felt I could trust based on my interactions with them, and who were just supportive along the way.”



Essential tools for today’s digital nomad

18:37 | 6 December

Dave Williams Contributor
A serial entrepreneur in the digital marketing, advertising, and ad tech industries, Dave Williams founded and sold 360i, IgnitionOne, BLiNQ Media, and other ventures and is now the CEO and Co-founder of NOMADX, with his base in Lisbon, Portugal.

The world isn’t ready for the digital nomad movement.

If projections are to be believed, the growing trend in how people choose to live and work is fast outpacing the service and policy enhancements needed to keep up with a borderless workforce bound only by its need for a reliable Wi-Fi connection. But that’s not slowing down the nomads.

that there could be as many as one billion remote workers by 2035. Such a movement has implications for entities ranging from banks and insurance companies to national governments — but few organizations are in the habit of looking 15 years down the road and altering course appropriately. But even short-term, the numbers deserve our attention: about 59 million people are considering joining the digital nomad movement in the next two to three years.

Put another way: in the next 24 to 36 months, roughly the population of Italy plans to sever traditional workplace ties so they can go mobile. How are our global services and infrastructures going to accommodate these individuals?

Having spent more than six years as a digital nomad myself, I can tell you that there’s a steep learning curve to this lifestyle. While it’s one that I’ve found well worth the effort, tapping into the networks and services needed to sustain my professional and personal networks hasn’t always been easy. Looking back to when I first gave into my wanderlust, after starting my career in the late ‘90s dot-com era as a serial entrepreneur in the U.S. digital marketing and ad tech industries, I can’t help but muse that I wish I knew then what I know now.

So for all of those aspiring or early stage nomads out there, in hopes that your own transitions to the nomadic lifestyle might be easier than my own, I’m here to tell you what I know now. While we can expect to see a great deal of change over the next couple decades, as the world economy races to catch up to the digital nomad movement, these are the essential considerations — and your best options — when it comes to the core elements needed to sustain yourself in your nomadic ramblings today.


Let’s start with the basics: where to live.

It’s almost impossible for digital nomads to find suitable accommodations at fair prices within major U.S. metropolitan areas that foster the standard of living they’re seeking. That’s one of the main reasons why so many nomads are ending up in Asian countries and other economical international destinations. In addition to being lower-cost, these destinations offer desirable alternatives to city environments where the standard 9-5 is required to afford everything the city has to offer.

When it comes to finding a place to live, whether for a few days or many months, there are a lot of options. The one that makes the most sense has a lot to do with your individual situation and preferences. Most important is having a place to stay with strong Wi-Fi. Consider:

Airbnb: Given its popularity for vacation rentals, a lot of new nomads initially turn here. While it allows for a more “at home” feel in a rental (because it is someone’s home), it can quickly become cost-prohibitive. Airbnb is great for short-term rentals, but comparatively expensive for anything more than a couple weeks.

Booking and Agoda: Similar to Airbnb, but these sites are more professional in that they’re mostly used by professionally-run apartments, hotels and resorts. All are great for those who are looking for more services with their accommodations. But they don’t always have the home-like feel that many nomads crave, and like Airbnb, they can get expensive fast.

Facebook Groups: A number of Facebook Groups for digital nomads have emerged recently. These groups can be handy because they let guests and hosts connect directly and come to mutually agreeable arrangements. However, these groups aren’t a rental platform. Guests don’t have access to reviews or an easy way to issue payments confidently. So while accommodations can be a bit more affordable when organized through groups, it’s hard to know what you’re going to get.

Hostels: As any rambling college student can attest, hostels are an affordable, social way to see the world. But living at a hostel offers little privacy and near-constant disruption, often of the drunken partying variety. It’s not a terribly viable route for nomadic couples or anyone looking for living space that can also double as an office. 

Hotels: On the flip side, hotels are great for couples. But for nomads spending weeks or even months abroad, they’re expensive and can be isolating for people looking to truly immerse themselves in new local cultures. Hotels are best reserved for short-term expeditions.

VIP hostels (e.g., Selina): This new breed of the hostel experience offers a great combination of co-working and social connections that help nomads connect with like-minded people. They provide some level of privacy, but these accommodations — like others — become expensive in the long term if you want your own bedroom.

Co-living spaces: As with co-working spaces, there’s a growing movement in which digital nomads come together to share the cost of living accommodations, which range from multi-bedroom apartments to large-scale co-living buildings complete with kitchens, shared and private bathrooms, working and community spaces. These environments are great for making connections while having access to privacy when needed, but branded co-living spaces will still cost more than a local midterm apartment.

Midterm rental platforms: For nomads looking to stay in one place for a month or more and truly soak in the culture, midterm rental platforms represent a more-affordable alternative to platforms like Airbnb. These platforms (full disclosure: I now operate one of them, by the name of NomadX) offer affordable month-to-month options with fast Wi-Fi in everyday neighborhoods, which enables you to connect more deeply with the local community without an overly long commitment. That said, this category is still quite new, so midterm rental inventory might be limited or nonexistent in the market you’re considering.

Couchsurfing: Finally, I’d be remiss not to mention Couchsurfing, a social network for travelers and nomads that makes it possible to connect directly with locals and even crash on their sofas for free. That said, Couchsurfing is only designed for short-term stays, it’s not very professional and it’s quickly evolving into more of a dating/hook-up platform than anything else.

Also, a quick note on Wi-Fi: No matter where you stay, you’ll need to ensure you can always be connected in order to stay on top of work. While you can check with your current mobile provider on international roaming plans, the coverage might be limited and ultimately become expensive. You might instead want to consider buying a local SIM card in every country and using it with your smartphone. That way, you can use your phone as a hotspot and get internet on your laptop. In a pinch, though, it’s good to have a backup mobile hotspot option. (For example, I travel with a Skyroam Solis.)


We digital nomads are risk takers by nature, but that doesn’t mean we don’t want or appreciate a safety net. After all, having an accident isn’t a choice. Unfortunately, if nomads can’t get coverage for a fair price, many opt to forego insurance altogether and end up resorting to crowdfunding if they end up in a bad situation. I’ve had several friends get into accidents in foreign countries, and they couldn’t get proper medical treatment until they’d crowdfunded the needed resources. This is a worst-case scenario, and it’s one that I hope becomes a thing of the past as more borderless options for insurance emerge.



A look at Latin America’s emerging fintech trends

23:28 | 5 December

Thiago Paiva Contributor
Thiago is a fintech entrepreneur, investor, and columnist. He is currently a product leader at Oyster, a neobank for SMEs in Latin America.

Although the 2008 global financial crisis sparked the fintech movement, in Latin America, the rise of ecommerce was responsible for the first wave of fintech startups.

Because digital payments were key to enabling the growth of ecommerce, investors funded companies like Braspag, PagSeguro, PayU, Mercado Pago and Moip in the early 2000s to take advantage of this opportunity.

Payment is still the most relevant segment, with successful cases like Stone and PagSeguro, but after the financial crisis, we started to see the rise of financial technology in lending and neobanking, generating impressive cases like Nubank, Neon, Creditas, Credijusto and Ualá.

As the ecosystem evolves and expands, let’s take a closer look at emerging trends in Latin America that might give us a hint about where to expect its next fintech unicorns.

Financial services for the gig economy

Latin America has seen explosive growth in ride-hailing and food delivery platforms such as Uber, Didi, Rappi and iFood, creating a totally new market opportunity — many gig economy workers can’t access basic financial services such as bank accounts, personal loans and insurance. Even those who have access often struggle with financial products that that don’t suit their needs because they were designed for full-time workers.

Spotting this opportunity, Uber Money launched at Money 2020, focusing on providing drivers with financial services. As 50% of the population in Latin America is unbanked where Uber has more than 1 million drivers, the region is definitely a ripe market. Cabify is going even farther by spinning off Lana, its company that provides financial services, so it can expand its market beyond Cabify drivers to include other gig economy professionals.

Although established players in this sector have a clear advantage, they aren’t the only ones looking to explore this opportunity; Brazilian YC alumni Zippi is offering personal loans to ride-hailing drivers based on their driving earnings. As the gig economy tends to keep growing in the region, I believe we will start to see more solutions for those professionals.

Rethinking insurance

As the banking world has been shaken by fintechs, insurance companies are growing aware that high regulatory barriers won’t protect their industry from disruption.

Insurance penetration in Latin America has been historically low compared to developed markets — 3.1%, compared to 8% — but the insurance market is growing well and tends to close this gap. Adding this to bad services and complex products that insurances provide, insurtech has an immense opportunity to grow.

Because purchasing insurance is historically a complicated and painful experience, the first insurtechs in the region focused on providing a better experience by digitizing the process and using online channels to acquire customers. Those insurtechs worked together with the insurance companies and operating as online broker, but now, we’re starting to see startups providing new insurance products, as well as traditional insurances in different models.

Some are partnering with insurance companies while others are competing directly with them; Think Seg and Miituo partnered with larger players to provide a pay-as-you-go model for car insurance, while Mango Life and Kakau are offering a better purchasing experience. On the other end, Crabi and Pier are rethinking the insurance model from the ground up.

As insurtechs emerge as a potential threat, incumbents are more willing to work with startups that can improve their services to enable them to compete on better grounds, which is exactly what companies such as Bdeo, Lisa, and HelloZum are doing.

Although penetrating the insurance industry is more complicated than other financial services due to high regulatory demands and steep initial operating costs, insurtechs fueled by VC investment will without any doubt try to do it. And, if we’ve learned anything from other fintech segments, it’s that entrepreneurs will find ways to overcome initial challenges.



How to build or invest in a startup without paying capital gains tax

02:09 | 5 December

Peyton Carr Contributor
Peyton Carr is a Financial Adviser to founders, entrepreneurs and their families, helping them with planning and investing. He is a Managing Director of Keystone Global Partners.
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Founders, entrepreneurs, and tech executives in the know realize they may be able to avoid paying tax on all or part of the gain from the sale of stock in their companies — assuming they qualify.

If you’re a founder who’s interested in exploring this opportunity, put careful consideration put into the formation, operation and selling of your company.

Qualified Small Business Stock (QSBS) presents a significant tax savings opportunity for people who create and invest in small businesses. It allows you to potentially exclude up to $10 million, or 10 times your tax basis, whichever is greater, from taxation. For example, if you invested $2 million in QSBS in 2012, and sell that stock after five years for $20 million (10x basis) you could pay zero federal capital gains tax on that gain. 

What is QSBS, and why is it important?

These tax savings can be so significant, that it’s one of a handful of high-priority items we’ll first discuss, when working with a founder or tech executive client. Surprisingly, most people in general either:

  1. Know a few basics about QSBS;
  2. Know they may have it, but don’t explore ways to leverage or protect it;
  3. Don’t know about it at all.

Founders who are scaling their companies usually have a lot on their minds, and tax savings and personal finance usually falls to the bottom of the list. For example, I recently met with someone who will walk away from their upcoming liquidity event with between $30-40 million. He qualifies for QSBS, but until our conversation, he hadn’t even considered leveraging it. 

Instead of paying long-term capital gains taxes, how does 0% sound? That’s right — you may be able to exclude up to 100% of your federal capital gains taxes from selling the stake in your company. If your company is a venture-backed tech startup (or was at one point), there’s a good chance you could qualify.

In this guide I speak specifically to QSBS on a federal tax level, however it’s important to note that many states such as New York follow the federal treatment of QSBS, while states such as California and Pennsylvania completely disallow the exclusion. There is a third group of states, including Massachusetts and New Jersey, that have their own modifications to the exclusion. Like everything else I speak about here, this should be reviewed with your legal and tax advisors.

My team and I recently spoke with a founder whose company was being acquired. She wanted to do some financial planning to understand how her personal balance sheet would look post-acquisition, which is a savvy move. 

We worked with her corporate counsel and accountant to obtain a QSBS representation from the company and modeled out the founder’s effective tax rate. She owned equity in the form of company shares, which met the criteria for qualifying as Section 1202 stock (QSBS). When she acquired the shares in 2012, her cost basis was basically zero. 

A few months after satisfying the five-year holding period, a public company acquired her business. Her company shares, first acquired for basically zero, were now worth $15 million. When she was able to sell her shares, the first $10 million of her capital gains were completely excluded from federal taxation — the remainder of her gain was taxed at long-term capital gains.

This founder saved millions of dollars in capital gains taxes after her liquidity event, and she’s not the exception! Most founders who run a venture-backed C Corporation tech company can qualify for QSBS if they acquire their stock early on. There are some exceptions. 

qsbs tax savings example

Do I have QSBS?

A frequently asked question as we start to discuss QSBS with our clients is: how do I know if I qualify? In general, you need to meet the following requirements:

  1. Your company is a Domestic C Corporation.
  2. Stock is acquired directly from the company.
  3. Stock has been held for over 5 years.
  4. Stock was issued after August 10th, 1993, and ideally, after September 27th, 2010 for a full 100% exclusion.qsbs stock acquired
  5. Aggregate gross assets of the company must have been $50 million or less when the stock was acquired.
  6. The business must be active, with 80% of its assets being used to run the business. It cannot be an investment entity. 
  7. The business cannot be an excluded business type such as, but not limited to: finance, professional services, mining/natural resources, hotel/restaurants, farming or any other business where the business reputation is a skill of one or more of the employees.

When in doubt, follow this flowchart to see if you qualify:



These new data sources are creating high-impact tools for investors

22:39 | 4 December

David Teten Contributor
David Teten is an advisor to emerging investment managers and a Venture Partner with HOF Capital. He was previously a partner for 8 years with HOF Capital and ff Venture Capital. David writes regularly at and @dteten.

Venture capitalists tout themselves as frontier technology investors, but most of us are using the same infrastructure tools we’ve used for the past 20+ years — Excel and recent college grads searching Google .

We’ve seen some modest progress in people upgrading from Excel to Google Sheets, along with the use of CRM and cloud-based storage services, but according to Sebastian Soler, who oversees data science at Lux Capital, less than 5% of American VCs have a full-time team member who’s focused on technology.

“While the arguments for adopting the latest technology are now too compelling to ignore, finding the required budget for specialized tools can often prove to be a major challenge, especially for smaller managers,” said Tim Friedman, founder of PEStack. “Comprehensive market data can cost upwards of $25k for a leading service, portfolio monitoring can be double that, add in front office tools and you’re quickly into six-figure sums. My advice is: there are now more products than ever which focus on quick implementation and offer a lot of functionality at a fraction of the cost of some of the larger legacy providers.

TotemVC* is one example of a high-quality solution that offers a powerful platform with a transparent, affordable monthly rate. One piece of advice would be to use a service like [PEStack’s] free Vendor Profiles platform to identify viable providers and build up a shortlist. We also track sample clients so that our users can see what their peers are using. I would always advise managers to talk to other professionals to get the real inside scoop on which products work well, how painful the implementation was, and how good the ongoing support is.”

Jonathan Balkin, founder of Lionpoint Group, observed that the highest-impact technology initiative for a new PE/VC fund is typically to configure and enforce usage of a CRM system. The next most impactful initiative is usually to create an easy-to-use LP portal.



Progressive VCs and private equity are using tech and analytics to revolutionize investing

03:34 | 4 December

David Teten Contributor
David Teten is an advisor to emerging investment managers and a Venture Partner with HOF Capital. He was previously a partner for 8 years with HOF Capital and ff Venture Capital. David writes regularly at and @dteten.

Private equity and venture capital investors are copying our counterparts in the hedge fund world: we’re trying to automate more of our job.

When I was single, I registered for (a lot of) dating websites. When I met my now-wife, I realized that any technology that can find me a spouse is a killer app. That’s why 40 million Americans use online dating sites. But, most of use raise capital and source deals the same way people looked for dates 20 years ago: networking at conferences (or bars).

Most of us want one spouse and we’re done, but in business, you want a lot of partners. I’d argue that the same type of technologies that have revolutionized dating can revolutionize our industry.

In liquid markets, most of the calories expended on technology and analytics are focused on trade selection, or “origination.” However, in private markets, there is more room to optimize across all 11 steps of the investing process. Below, I’ll walk through how progressive investors are using technology and analytics throughout all of their operations. To learn more about this space, I suggest joining an online community I co-founded, PEVCTech.

1) Managing the firm 

Before you can actually invest, you have to manage your fund. This is harder than it sounds. In the private equity universe, most partners have primary training as deal-makers, not as managers. When I talk with junior personnel at private equity firms, the quality of firm management is a frequent complaint.

I’ve used Asana extensively to manage activities firm-wide. I also use several living Google docs to maintain the minutes and the group agendas for my fixed weekly meetings. I use another live Google doc to maintain my database of companies I’m marketing to other VCs. That Google document provides cut and pasteable text I can share with other investors, based on their stage, focus and appetite.

Other investors use Trello, Basecamp, and Monday for making sure that everyone at the firm knows each others’ long-term OKRs and short-term projects. Point Nine Capital uses 15Five for continuous employee feedback.

One aspect of management which merits attention is your own cybersecurity, which should not be left until a crisis to address. Small investment firms often have interns and entrepreneurs in residence passing through, each of which is a security risk. (See A comprehensive guide to security for startups by Bessemer Ventures.)

2) Marketing

Kyle Dunn, CEO of Meyler Capital, says “investors should focus on building a large audience within a CRM system (having the ability to categorize your different constituents); communicate consistently to that audience; and implement an automation platform that can leverage lead score to profile interest. It sounds simple; however, very few asset managers actually do it.” I agree.

Many tools designed for B2B marketing in general are also relevant to investors. I know of funds using Constant Contact, Goodbits, Pardot and Publicate to create light newsletters for internal and external consumption. A major angel group uses Influitive, an advocate management tool, to track, activate and motivate their members. Other VCs use Contently* or Social Native* to create relevant content. Meyler Capital is taking the analytical rigor of modern internet marketing and applying it to fund marketing.

Point Nine Capital’s website is now powered by Contentful — it uses Unbounce for landing pages and Typeform for surveys and other data collection. “We’re using … TinyLetter for our “Content Newsletter” … and Buffer to schedule social media posts. Last but not least, we still use MailChimp to publish our (in)famous newsletter.”  I also use Mailchimp for the and mailing lists. Point Nine Capital uses Mention for media monitoring. is built on WordPress as my content management system.

I use Hootsuite to coordinate my social media activity, which consists of,, Linkedin, AngelList, and (passively) Twitter and Facebook. I use Google Drive to host my conference presentations, which are all embedded at I use Diigo, a social bookmarking tool, to keep a record of useful websites.  I have also configured IFTTT to share on Twitter anything new I post on Diigo.

Qnary is one of numerous tools which can help build out your team members’ virtual presence. A tool like Quuu identifies relevant, shareable content to keep your social media channels active.

“There are two crucial aspects of marketing that investors often overlook: automation and analytics,” wrote Sabena Quan-Hin, Marketing Manager at Flow Capital. “Automation allows you to spend less time on tedious tasks and will help boost productivity, especially within a small marketing team. At Flow Capital, we use HubSpot’s sequences and workflows functions to automate a bulk of our emails and internal tasks. This provides us more time to develop meaningful relationships with prospects and customers. We use Google Analytics, HubSpot, and LinkedIn Campaign Manager for the majority of our analytics. For our content creation, we use tools such as Canva (graphic design) and GoToStage (webinars platform) to create and share content for prospects to find.”

3) Raising capital

Tim Friedman, Founder, PE Stack, said, “If I could offer one piece of advice to today’s managers, it would be to take the time to understand the demands of the modern institutional LP. Today’s investors are allocating more to alternatives in an environment where there are record numbers of new funds; and seeking deeper relationships with managers via direct and coinvestments. The past few years have therefore seen a huge rise in the proportion of LPs using specialized tools to manage and understand their portfolios, including platforms such as Chronograph, Solovis, Allocator, Cobalt LP, eFront Insights, iLevel, Burgiss.

The proportion of LPs using technology to manage their portfolios will continue to increase, and GPs unable to provide quality data to LPs will find it increasingly hard to retain and attract LPs. We are also seeing technology evaluation as an increasingly important part of LP operational due diligence. Excel and Google simply aren’t going to cut it if you expect to build a high quality institutional investor base.”

A more efficient approach to fundraising than haphazard networking is to mine the data exhaust from the limited partner universe to identify those LPs most likely to find your fund attractive and focus all your energy on them. I previously posted a detailed presentation with sales technology tools useful for B2B sales.

I always make a point of keeping firm records updated in the major data-trackers tracking the VC industry: AngelList, CB Insights, Crunchbase, Dow Jones VentureSource, Pitchbook, Preqin, and Refinitiv Eikon. LPs, coinvestors, and press use these tools, so I work for free for these data vendors to make sure that their data about our activities is correct. This is a great example of why data businesses have substantial moats.

Boardex and Relationship Science make it easier to understand and map social networks into potential limited partners. Cobalt for General Partners helps GPs to optimize their fundraising strategy. MandateWire and FinSearches provide leads on limited partners with new mandates which might fit your fund. Evestment is a platform for capital-raisers; Evestment TopQ automates private markets performance calculation.

I am a heavy user of DocSend, a secure content sharing and tracking platform that can be used to seamlessly share recurring materials with potential LPs. It provides analytics to track shared materials across target senders and improve the content for future leads. Point Nine Capital uses Qwilr to create modern, mobile-native collateral.

Most funds open data rooms to share previous reports, performance data, pitch decks, legal docs and other fundraising material with LPs. I’ve seen funds using Ansarada, Allvue, Box, CapLinked, dfsco, Dropbox, Digify, Drooms, Google Drive, iDeals, Intralinks, Ipreo, Merrill Corporation, and SecureDocs for their Virtual Data Rooms. These same tools are used by companies raising capital.

I’ve also experimented with using services which are marketplaces between LPs and GPs: CEPRES, DiligenceVault, FundVeil, Harvest Exchange, and Palico. Some funds are using technology-enabled intermediaries to help them sell to retail LPs, e.g., Artivest and iCapital Network.

Deer Isle Group has built the D.I.G. Beacon technology system, which automatically outbound-solicits a universe of over 10,000 institutional investors, without requiring LPs to register for an online network of funds.

Crystal guides you in how to influence a particular person, based on their online presence. is a virtual assistant which can coordinate your fundraising and other meetings.



Does your company cultivate inclusion?

22:09 | 3 December

Lauren McCaslin Contributor
Lauren McCaslin is a vulnerability verification specialist with application security leader WhiteHat Security.

Each company’s culture is defined by a variety of factors.

One major factor is its leadership, and the type of workplace environment they choose to create. For example, are they approachable and encourage collaboration from all levels of the organization? Or do they prefer to maintain a tightly knit power structure, working only within the C-suite, from a rigid, top-down structure?

I’m quite fortunate to work for an employer with a culture that focuses on empowering and valuing the contributions of women equally to men at all levels of the organization. I recognize the gift that this culture is because sadly, not every company is like this. Tech companies especially must increase efforts to enable and encourage women with inspiration and opportunities that drive success. In fact, research has shown that companies with gender diversity in leadership experience greater financial returns.

So, how can other companies become more inclusive? The goal is identifying the right mix of ideas to create or institute programs that are unique but fit within the company’s mission and workplace culture. While the program at my employer is still being defined and developed, we have some great ideas for kickstarting an inclusive program that can be successful for your team, such as:

Create a community and attend events that expand your network

Getting involved in community events that are focused on women, like Women of Silicon Valley, is one way my team has made critical connections with the local talent pool and other female leaders in the Bay area. This creates significant value for our organization over time, and the investment in participation cannot be overstated. Partnering with those outside your company can also foster inclusive workforces, and that is a win-win.

Taking this a step further, we’ve also invited speakers to speak to our female employees on topics ranging from career development or tips and tools for avoiding imposter syndrome, to strategies for engaging with peers in the workplace and fostering more productivity.

As a developing program, I believe the inclusive initiatives at my company put them ahead of many others in Silicon Valley. The organization partners with our PR firm to identify and take advantage of industry speaking engagements, such as DefendCon and the Women in Tech Summits, to highlight female thought leaders, as well as industry award programs like Women in IT, that recognize significant achievements of female engineers in our market.

We are also currently pursuing a workshop for women to help them maximize their professional LinkedIn profiles. Here, our female employees will examine their own profiles to determine if their value is clearly articulated. They will be given suggestions on strengthening their profiles and representing their experience, and also have professional photos taken.

Finally, our company looks for ways to lift up women employees and celebrate their presence. As an example, we recently acknowledged International Women’s Day with a luncheon hosted by executive leadership for women in all departments, praising their contributions and the vital role they have in our company’s continued success.

Keep interoffice communication productive and professional, but also social

Having a dedicated interoffice communication channel where women engineers can go to ask questions or offer support to other women is very beneficial.

At my company, female employees at every level of the organization utilize a Slack group to collaborate and share information. Here, inclusion is immediate as you’re welcomed on your first day of employment and invited to contribute to the group.

The general vibe of our Slack channel is about ‘women empowering women.’ We encourage and lift each other up. Our team vice president also keeps us informed about special events and opportunities that might be of interest.

We also use the channel as a professional resource, whether it’s to brainstorm ideas, to share industry articles featuring other powerful women killing it in tech, or to communicate opportunities for professional development and upskilling that might benefit us all.

This exclusively women’s outlet has grown quite important to us, especially as our company was acquired earlier this year. As roles have evolved, women are finding support from one another and receiving encouragement as they adjust to new tasks and responsibilities.

This cultural empowerment is a movement for our company, and you can see it in how women will flock toward each other. For example, it’s noticeable in meetings how colleagues celebrate the successful completion of a project or amplify a great idea by eagerly offering support and congratulations.

These obvious benefits have spawned the idea to create group ‘empowerment chapters’ in each of our global offices in Houston, Belfast, and San Jose, where women will take turns acting as a chairperson and coordinator for that particular location. Since a company’s culture is also impacted by its physical geography within the world, or whether it is located in an urban or rural area, these chapters can enhance our understanding of colleagues in different parts of the world.

Use same-gender mentorship to build a more diverse workforce

Executive leaders are recognizing that in order to promote continued learning, stronger job performance, and swift career advancement that results in employees remaining with their organization longer, they must provide inclusive and effective mentors and sponsors. For men or women, the emphasis can be less on hierarchy and more on reciprocity, so companies can develop and provide mutual mentoring pairs.

The mentoring program for my team focuses women employees on increasing the inclusivity of women in the workspace; sharing motivational messages on being a woman in tech and recognizing and celebrating the successes of individuals within a group. These relationships help women to overcome individual challenges with the existing organizational hierarchy and quickly address progress-killing power dynamics that might be in play.

As an expansion of our mentorship program, we have also made a point to impress upon the recruiters and hiring consultants that we work with, to help with our efforts by identifying and delivering a more diverse pool of job candidates to apply for open positions within the organization. Being upfront and transparent about this requirement means that we’re actively fostering greater inclusion and diversity from the very beginning of a woman’s career with us – and it is supported from the top-down in the org chart. We even target colleges and universities with a favorable diversity profile to recruit interns and entry-level employees.

The U.S. recently celebrated Women’s Equality Day, commemorating the passage of the 19th Amendment to the U.S. Constitution, granting the right for women to vote. This amendment was hard-earned by 19th century women, who previously had little opportunity to assert their opinions or individuality.

Generations of women since then have had a vastly different life experience. Our aim as women is to keep pushing this effort forward. One way to do that is recognizing how much women contribute to the workplace and impact our corporate culture.

I heard a quote once that really resonates with me: “Diversity is being invited to the party, but inclusion is being asked to dance.” Explicitly defining and sharing criteria for advancement, offering exciting assignments to all employees, and most importantly, expecting, reinforcing and rewarding intentional inclusion can go a long way toward strengthening a positive corporate culture.

It’s expected that corporate culture may change over time, being re-shaped or molded by the influx of new people, new places and new ideas. Therefore, it takes some effort to develop a strong culture that continues to reflect the company’s values and ensures that any changes are still appropriately meeting the needs of every employee, while delivering on the company’s core mission.

We must address the workplace status quo and force organizations to address biases and stereotypes, or risk reinforcing gender inequalities. Promoting a corporate culture where talented professional women associate and engage with other professional women or advocates of women at varied career levels may be the revolution needed to truly transform workplace gender inclusion.


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