Technology

According to a report from Bloomberg, the Trump campaign called dibs on some of the most prized ad space online in the days leading up to the 2020 U.S. election.

Starting in early November and continuing onto Election Day itself, the campaign will reportedly command YouTube masthead, the space at the very top of the video sharing sitehomepage. YouTube is now the second most popular website globally after the online video platform overtook Facebook in web traffic back in 2018. Bloomberg didn&t report the details of the purchase, but the YouTube masthead space is reported to cost as much as a million dollars a day.

The Trump campaignad buy is likely to rub the presidentmany critics the wrong way, but it isn&t unprecedented. In 2012, the Obama campaign bought the same space before Mitt Romney landed the Republican nomination. Italso not a first for the Trump campaign, which bought banner ads at the top of YouTube last June to send its own message during the first Democratic debate.

Screenshot of the Trump campaignJune 2019 YouTube ads via NPR/YouTube

In spite of the precedent, 2020 is a very different year for political money flowing to tech companies — one with a great degree of newfound scrutiny. The big tech platforms are still honing their respective rules for political advertising as November inches closer, but the kinks are far from ironed out and the awkward dance between politics and tech continues.

The fluidity of the situation is a boon to campaigns eager to plow massive amounts of cash into tech platforms. Facebook remains under scrutiny for its willingness to accept money for political ads containing misleading claims, even as the company is showered in cash by 2020 campaigns. Most notable among them is the controversial candidacy of multi-billionaire Mike Bloomberg, who spent a whopping $33 million on Facebook alone in the last 30 days. In spite of its contentious political ad policies, much-maligned Facebook offers a surprising degree of transparency around what runs on its platform through its robust political ad library, a tool that arose out of the controversy surrounding the 2016 U.S. election.

On the other end of the spectrum, Twitter opted to ban political ads altogether, andis currently working on a way to label &synthetic or manipulated media& intended to mislead users — an effort that could flag non-paid content by candidates, including a recent debate video doctored by the Bloomberg campaign. Twitter is working through its own policy issues in a relatively public way, embracing trial-and-error rather than carving its rules in stone.

Unlike Twitter, YouTube will continue to run political ads, but did mysteriously remove a batch of 300 Trump campaign ads last year without disclosing what policy the ads had violated. Google also announced that it would limit election ad targeting to a few high-level categories (age, gender and ZIP code), a decision the Trump campaign called the &muzzling of political speech.& In spite of its strong stance on microtargeting, Googlepolicies around allowing lies in political ads fall closer to Facebookanything-goes approach. Google makes a few exceptions, disallowing &misleading claims about the census process& and &false claims that could significantly undermine participation or trust in an electoral or democratic process,& the latter of which leaves an amphitheater-sized amount of room for interpretation.

In recent years, much of the criticism around political advertising has centered around the practice of microtargeting ads to hyper-specific sets of users, a potent technique made possible by the amount of personal data collected by modern social platforms and a strategy very much back in action in 2020. While Trumpcampaign leveraged that phenomenon to great success in 2016, Trumpbig YouTube ad buy is just one part of an effort to see what sticks, advertising to anybody and everybody in the splashiest spot online in the process.

YouTube declined to confirm to TechCrunch the Trump campaignreported ad buy, but noted that the practice of buying the YouTube masthead is &common& during elections.

&In the past, campaigns, PACs, and other political groups have run various types of ads leading up to election day,& the spokesperson said. &All advertisers follow the same process and are welcome to purchase the masthead space as long as their ads comply with our policies.&

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Today we bring you another edition of &Dear Sophie,& an advice column that answers readers& questions about immigration for tech.

&Your questions are vital to the spread of knowledge that allows people all over the world to rise above borders and pursue their dreams,& says Sophie Alcorn, Silicon Valley immigration attorney. &Whether you&re in people ops, a founder, or seeking a job in Silicon Valley, I would love to answer your questions in my next column.&

Dear Readers,

Today I&m sharing answers to the most frequently asked questions following up to the last H-1B Dear Sophie. Fortunately, the government has provided a lot more details over the last few weeks. Additional info about the electronic registration process is available on my H-1B podcast. Enjoy!

Am I limited to sponsoring somebody in the lottery to a maximum of three times?

No, there is no limit to how many times a company can sponsor an individual. A lot of companies tend to do it three times because candidates can often work for you for three years with OPT and STEM OPT, but the law doesn&t set out an upper limit. Also, you can sponsor current F-1 students as well as people who have accepted your offers who are currently outside the United States.

I&m in HR. When can I create my profile for H-1B electronic registration?

You can access my.uscis.gov starting February 24, 2020 at 10 a.m. (EST) to create your profile for the electronic registration process. However, employers will not be able to create registrations for your employees and candidates until March 1st at noon.

I&m working with a lawyer; which category should I select for my my.uscis.gov profile?

This is counterintuitive. If you&re working with an attorney, on the Account Type screen, don&t select the box for &I am an applicant, petitioner, or requestor.& Instead, select the &I am an H-1B registrant& box.

When can I actually register my employees and people who accepted our job offers?

The initial registration period starts March 1, 2020 and is supposed to run through March 20, 2020. USCIS will announce the actual end date of the initial registration period on its website. If not enough people register (unlikely), USCIS can decide to re-open registrations.

How do I add my lawyer to the my.uscis.gov account?

Your attorney will provide a &representative passcode& that you need to enter. This will take you to the G-28 page where you can accept your representative. Talk to your attorney about whether they prefer that you have USCIS send notices to you or their firm.

How many people can I register?

You can enter up to 250 people in one batch and you can review them before you submit.

What if I make a mistake when registering somebody?

You should be able to delete entries even after having submitted them. The website will warn you if there is missing information, but cannot warn you about inaccurate information.

Can I register the same person more than once?

No, don&t do it. Itagainst the rules and you will forfeit this personopportunity to get an H-1B.

When are we supposed to file full I-129 petitions with all the supporting documents?

For each of your selected candidates, you will receive a selection notice listing the 90-day filing window deadline and the physical mailing address to send the petition package. Therefore, most petitions will be submitted April through June.

What if we electronically register somebody in good faith but we can&t go through with the petition?

USCIS is trusting your company to act in good faith. Make sure that for any candidate you electronically register, they have accepted a position with your company and you actually intend to follow through with hiring them. However, there is currently no requirement to notify USCIS if you won&t be following through with filing the full petition for a selected registration.

Can a current student be included in the &Mastercap?&

The advanced degree exemption to the H-1B lottery is for candidates who have received masterdegrees and PhDs from U.S. universities. They have a higher chance of lottery selection. Under the new electronic registration system, you have to prove eligibility at the time of filing the physical petition, not at the time of electronic registration. So if somebody is graduating in May or June, you check the Mastercap box for them in March. However, itsafest to wait to get their proof of graduation before submitting the full I-129 package.

What are the chances?

Last year, there were more than 200,000 petitions. There are 65,000 available H-1Bs plus 20,000 for the Mastercap. Just how many petitions will be filed with the new electronic registration system remains to be seen.

Will premium processing continue to be available?

I don&t know, my crystal ball isn&t giving me information on this one right now. ;)

Have a question? Ask it here; we reserve the right to edit your submission for clarity and or space. The information provided in &Dear Sophie& is general information and not legal advice. For more information on the limitations of &Dear Sophie,& please view our full disclaimer here.

Have a story to share about how you navigated immigration to build your dreams? Apply to guest on Sophiepodcast about immigration law for tech startups.

Future &Dear Sophie& columns will be accessible for Extra Crunch subscribers; use promo code ALCORN to purchase a one or two-year subscription for 50% off.

Tyler Haney, the founder and chief executive of activewear label Outdoor Voices, has stepped down, the company confirmed for us this afternoon.

The Business of Fashion, which first reported the news, said the transition follows a previously unreported capital injection from Outdoor Voices& investors at a lower valuation than previous rounds. It says the company tried raising new funding late last year but &had difficulty.&

We reached out to Haney directly earlier today, as well as board members from the venture firms that have backed the company, including General Catalyst and Forerunner Ventures. In the meantime, the company sent us the following: &As we look to grow and to scale, Tyler Haney has transitioned from her role as Chief Executive of Outdoor Voices to a new position as Founder. We have raised another round of financing from our current investor group to support our growth and expansion moving forward. Tyler will remain a member of the Board of Directors and will assist with the search for a new CEO. Until we fill that role, Cliff Moskowitz will serve as the CompanyInterim CEO.&

BoF cites executive turnover as an earlier indicator that not all was well within the company, suggesting that mismanagement was one factor that prompted Pamela Catlett — a former Nike and Under Armour exec — to leave the company months after joining as president last year.

Retail legend Mickey Drexler, formerly of J.Crew fame — who was named chairman of Outdoor Voices& board in the summer of 2017 as part of a $9 million convertible debt round led by Drexlerfamily office — also resigned his position last year, though he maintained a directorseat.

Operational challenges aside, according to BoF, Outdoor Voices has had trouble replicating the kind of excitement that met its earliest offerings, including flattering, color-blocked athleisure wear, like leggings, sports bras, tees and tanks.

The company has since rolled out an exercise dress that has gained traction with some consumers, but newer offerings meant to extend the brandreach, including solidly colored hoodies and terrycloth jogging pants that are less distinguishable from other offerings in the market, have apparently failed to boost sales.

Indeed, according to the BoF report,the brand was losing up to $2 million per month last year on annual sales of around $40 million.

The BoF story doesn&t mention the companybrick-and-mortar locations and how they factor into the companynarrative. But certainly, as with a growing number of direct-to-consumer brands that have been encouraged by their backers to open real-world locations, they&ve become a major cost center for the outfit. Outdoor Voices now has 11 locations around the U.S., including in Austin, LA, Soho in New York, Boston, Nashville, Chicago and Washington, D.C.

Even with (at least) $64 million in funding that Outdoor Voices has raised from investors over the years, italso going head-to-head with very powerful, very entrenched and endurably popular brands, including Nike and Adidas. While Outdoor Voices is still in the fight, the shoe and apparel giants have vanquished plenty of upstarts over the years.

What happens next to Haney — a former track athlete from Boulder who first launched the business with a Parsons School of Design classmate — isn&t yet clear. Still, she isn&t going far, reportedly. BoF says she still owns 10% of Outdoor Voices and will remain engaged with the company.

Correction: An earlier version of this story incorrectly associated Moskowitz with a different InterLuxe in New York. Apologies for the confusion.

Featured above, left to right, Emily Weiss of Glossier and Tyler Haney of Outdoor Voices at a 2017 Disrupt event.