Help Needed Navigating CTO Issues

Apologies in advance for a fairly long post, but I am having issues with someone we brought on in the CTO position and I would love to get some feedback from anyone who has gone through something similar.

About 10 months ago now, I hatched a business plan with a close friend and co-worker who we can call Andrew. Andrew and I spent April to August interviewing users in our target market about our idea, gathering feedback, honing our business plan and model, and planning as best as we could a product roadmap for our business. Andrew has great connections with some Angel investors, and I have connections with our target users in our target city. As a result, we were able to secure a friends & family round of funding. However, neither of us is technical enough to build the product by ourselves, so we needed to bring on an engineer to focus on building the product. We reached out to a former coworker (and close friend of Andrew) who we can call Sara. Sara negotiated hard for 33% of the company, and we agreed, with the understanding that the bulk of the upcoming work would be on her shoulders. We discussed this plainly at the time – she made it clear that she would be doing everything from a product development perspective, and for that reason deserved equal share.

She agreed to work as our CTO in late August/early September, but she told us she could not work on the business at all until she was full time and salaried. This seemed reasonable at the time, and we had plenty of funding for all of us to work full time on the project starting November 1st. She then told us that all of November would be used for planning purposes, and she did not write a line of code until early December. In mid-December, we hired a front end engineer that Andrew and I knew from our time working together. He focuses solely on the frontend while Sara focuses solely on the backend and has not taken on any frontend tasks.

In early January, I started to notice on Github, Jira, Slack, etc. that Sara was extremely inactive for long stretches of the day. She would make one or two PR's in a day that seemed trivial and minimal effort. It is worth mentioning that I worked as a Data Engineer and am familiar to some degree with SQL, Python, Jira/project management on engineering teams, so I knew what an engineer of her experience level could accomplish. We spoke with Sara over a month ago now about this behavior, and she told us that she did not feel "excited" about the idea or the business in general and that she had been struggling to motivate herself for several weeks. This was obviously a major red flag to me and we told her that we expected and needed a lot more from her.

Fast forward another month, and we have had multiple conversations with her about her effort level and commitment. She has definitely improved from an effort perspective, but other issues remain. For example, she does not seem to have a vision for the technical side of the product and has continued to move slowly. I am the one laying out all of the features we need developed, setting timelines/goals, etc. Our engineering progress has been so slow, in fact, that we are hiring 2 additional engineers to try to pick up the pace. This unsettles me quite a bit considering we are pre-revenue and pre-product, and from my perspective, I felt as though we would have been better off moving on from her several weeks ago and focusing our efforts on finding someone who matches Andrew and my excitement and work ethic for the business.

This situation is made more complicated by the fact that Andrew & Sara were close friends prior to launching this business. Andrew is hesitant to move on before we have a "plan B" in place. I have tried reaching out to other people in my network, but it is limited and overlaps quite a bit with Sara's network. I am considering making an anonymous post on some job boards to see if I can drum up any interest, but it is obviously difficult to find a replacement when we can't post publicly on any job sites.

It is difficult to work with an "equal partner" who works fewer hours, is openly apathetic (at times), and has overall created a ton of additional work/stress for myself and Andrew (because we have to monitor her work and have frequent check-ins with her).

I would love to hear from anyone who has been through anything similar. I'm looking for any advice and I appreciate it in advance! I'm more than happy to answer any additional questions if anything is unclear.

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Online workspace startup Notion hit by outage, citing DNS issues

Notion, the online workspace startup that was last year valued at over $ 2 billion, was knocked offline after a DNS outage.

The collaborative online office and document service was not loading as of around 9 a.m. ET on Friday, preventing anyone who relies on the service from accessing their cloud-stored data.

In a since-deleted tweet, Notion asked if “any users have a contact at,” the web host that Notion relies on for its domain name. In a reply, said it was “working with the owners of this domain to address this issue as quickly as possible.” Notion replied: “Could you let us know where you’re messaging us to address this?”

The now-partially deleted tweet thread noting the apparent Notion outage. (Image: TechCrunch)

In a statement shortly after its first tweet went out, Notion told TechCrunch: “We’re experiencing a DNS issue, causing the site to not resolve for many users. We are actively looking into this issue, and will update you with more information as we receive it via our status page on Twitter.”

Notion didn’t say specifically what the DNS issue is. Domain name servers, or DNS, is an important part of how the internet works. Every time you go to visit a website, your browser uses a DNS server to convert web addresses to machine-readable IP addresses to locate where a web page is located on the internet. But if a website or its DNS server is not configured correctly, it can cause the website not to load.

It’s not clear exactly who is responsible for this particular DNS issue. When reached, a spokesperson for did not immediately comment, and, the Somali-based registrar that oversees the .so country-code top level domain on which Notion relies, did not return a request for comment.

We’ll update once we know more.

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The SEC statement does specify that it believes the “core market infrastructure” remains intact despite the heavy trading volumes of the past week, which were prompted primarily by activity organized by retail investors acting in concert through organization on r/WallStreetBets, a subreddit dedicated to day trading. These retail investors resolved to collectively purchase and hold GME stocks (and subsequently, shares in other companies like movie theater chain AMC) in a bid to sweat out hedge funds with significant short positions in the same.

The ensuing high volume of trading activity from individual retail investors led to various actions from platforms that provide free trading to these individuals, including Robinhood, Webull, Public and M1. Robinhood initially cited “protecting” its users as the reason for limits imposed, but later revealed that a lack of funding to cover trade clearances likely caused the temporary measures, since it tapped $ 500 million to $ 600 million in credit facility and raised $ 1 billion in funding overnight.

The SEC’s statement includes a callout that seems specifically directed at entities like Robinhood, and it’s fair to interpret it as a warning:

In addition, we will act to protect retail investors when the facts demonstrate abusive or manipulative trading activity that is prohibited by the federal securities laws. Market participants should be careful to avoid such activity. Likewise, issuers must ensure compliance with the federal securities laws for any contemplated offers or sales of their own securities.

Robinhood has already had run-ins with the financial regulator for unrelated business practices. Meanwhile, lawmakers from both the House and the Senate, as well as NY AG Letitia James have all expressed their intent to review the event and all surrounding activities, which likely involves the role trading platforms like Robinhood played in the week’s events.

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