{"id":357694,"date":"2025-11-05T15:19:15","date_gmt":"2025-11-05T15:19:15","guid":{"rendered":"https:\/\/www.europesays.com\/us\/357694\/"},"modified":"2025-11-05T15:19:15","modified_gmt":"2025-11-05T15:19:15","slug":"i-left-my-15-year-career-for-startups-the-risk-was-worth-it","status":"publish","type":"post","link":"https:\/\/www.europesays.com\/us\/357694\/","title":{"rendered":"I Left My 15-Year Career for Startups. the Risk Was Worth It."},"content":{"rendered":"<p>This as-told-to essay is based on a conversation with Robert E. Williams, a 40-year-old VC board director and startup advisor based in Maryland. It&#8217;s been edited for length and clarity.<\/p>\n<p>I spent the first 13 years of my career at AT&amp;T, working my way up to an assistant VP-level position. Then, I remember asking myself a question that unlocked a complete shift in what I wanted: If all the <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/left-big-tech-watching-middle-managers-struggle-2025-10\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">money and safety<\/a> were to blow up in Big Tech, what would I really want to do?<\/p>\n<p>In 2021, I left AT&amp;T and stepped down from my title to take a bet on myself. After a series of calculated career risks, I joined an AI startup, and now I work in venture capital as an advisor for startups I believe in.<\/p>\n<p>The <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/quit-big-tech-to-work-ai-startup-pros-and-cons-2025-9\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">startup world has been invigorating<\/a> and completely unlike the past predictability of Big Tech. If Big Tech is a luxury yacht, then startups are a speedboat.<\/p>\n<p>I loved a lot of things about my time in tech<\/p>\n<p>In 2007, I came straight out of undergrad into an account executive role at AT&amp;T, where I had a really supportive development system around me and was able to take on a lot of responsibility quickly. I met some great people and had mentors who really showed me the ropes. Plus, the money was safe, which meant a lot as a young twenty-something.<\/p>\n<p>I worked my way up from sales manager to director and was eventually <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/former-google-engineer-work-life-balance-better-at-startup-2022-12\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">promoted to an assistant VP role<\/a> in 2018. I had a lot of responsibility, but everything felt very structured.<\/p>\n<p>From weekly meeting cadences to quarterly business reviews, I always knew the playbook we&#8217;d run for that day, week, and month.<\/p>\n<p>During the pandemic, I had a lot more time to think about what was important to me<\/p>\n<p>While I valued the stability of a big company, the relationships I built, and my time leading large teams, I wanted to expand my experiences into the <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/ai-job-market-indeed-top-tech-roles-getting-chopped-most-2025-8\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">growth areas of tech<\/a>. In 2020, that was the cloud and the earlier days of AI and machine learning.<\/p>\n<p>                      Related stories<\/p>\n<p>                                <img decoding=\"async\" class=\"lazy-image \" viewbox=\"0 0 1 1\" src=\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/07\/placeholder.png\" alt=\"\"\/><\/p>\n<p>                            Business Insider tells the innovative stories you want to know<\/p>\n<p>                                <img decoding=\"async\" class=\"lazy-image \" viewbox=\"0 0 1 1\" src=\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/07\/placeholder.png\" alt=\"\"\/><\/p>\n<p>                            Business Insider tells the innovative stories you want to know<\/p>\n<p>I wasn&#8217;t ready to make the startup leap yet, but I knew I needed to join an established company with a culture of innovation and disruption in emerging tech. When <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/workplace-loyalty-corporate-america-dysfunction-employers-employees-att-jobs-2025-9\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">I left AT&amp;T<\/a>, I joined AWS as a sales leader. It was a calculated risk, but I was willing to bet on myself to prove that I could thrive in this new environment.<\/p>\n<p>A year later, I took another calculated step down to a startup-style division of Palo Alto Networks, and then I felt ready to go all in on startups.<\/p>\n<p>I found startup life invigorating<\/p>\n<p>In 2023, I joined an AI and quantum startup as its head of global channels, and later its head of revenue and partnerships. We were building partnerships around the world, so I was probably on a plane at least every other week, getting in front of customers.<\/p>\n<p>I worked most days from 7 a.m. to 7 p.m., building the team, responding to customers, and <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/haggling-negotiate-better-price-2024-9\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">negotiating contracts<\/a>. My scope of work was much broader than it ever was in Big Tech, and it was invigorating. I&#8217;d quickly see the fruits of my labor as new customers, partnerships, and media came through.<\/p>\n<p>The startup world is inherently unpredictable, and I had to wear a lot of hats<\/p>\n<p>In one moment, you could be helping the team respond to a critical RFP response deadline, and then in another, you&#8217;d be briefing investors from a $100M VC fund.<\/p>\n<p><a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/startup-success-secret-vcs-founders-nate-silver-on-the-edge-2024-8\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">The pay is high risk<\/a>, high reward. It&#8217;s very common to forgo some of the typical Big Tech cash &#8220;on target earnings&#8221; for additional equity upside. I found it important to have a genuine conviction in both the market and the startup before making that tradeoff. It needs to fit into your lifestyle goals for three to five years until an exit event.<\/p>\n<p>Now, as a VC, I have more time to focus on what matters to me<\/p>\n<p>There wasn&#8217;t anything I disliked about startup life, but after a few years, I wanted to scale that impact across multiple companies.<\/p>\n<p>In May, I stepped down to an advisor role at the startup, which allowed me to become a board of director for a VC, and an advisor for two other startups: one fintech company and one medical device startup in Africa.<\/p>\n<p>Even though I&#8217;m covering more ground in terms of companies,<a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/ways-to-be-more-productive-manage-time-better-experts-2018-12\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\"> I&#8217;ve gotten so much time<\/a> back, not having to be on a plane every week. I&#8217;ve been spending more quality time with family and reconnecting with old friends that I haven&#8217;t seen in some time.<\/p>\n<p>I&#8217;ve also had time to double down on mentorship and advisory work with startup founders and students from historically underrepresented groups.<\/p>\n<p>The most important thing to do in your career is find out what you&#8217;re functionally good at<\/p>\n<p>At a startup, you can have a lot of individual impact. You can take the risk of getting equity and stock options, but you have to remember that <a target=\"_self\" class=\"\" href=\"https:\/\/www.businessinsider.com\/had-4-startups-fail-before-1-took-off-heres-what-learned-2025-1\" data-track-click=\"{&quot;element_name&quot;:&quot;body_link&quot;,&quot;event&quot;:&quot;tout_click&quot;,&quot;index&quot;:&quot;bi_value_unassigned&quot;,&quot;product_field&quot;:&quot;bi_value_unassigned&quot;}\" rel=\"nofollow noopener\">most startups fail<\/a>. That being said, when you consider reduced job security and the AI boom, Big Tech isn&#8217;t the safe option it used to be.<\/p>\n<p>Beyond anything else, it&#8217;s important to find out what you&#8217;re functionally good at. I&#8217;m great at go-to-market business development and strategic partnerships, and that&#8217;s been my anchor throughout my career.<\/p>\n<p>If you can narrow in on what you&#8217;re good at, you&#8217;ll be incredibly valuable in Big Tech or startups.<\/p>\n<p>Do you have a story to share about quitting Big Tech? If so, please contact the reporter at tmartinelli@businessinsider.com.<\/p>\n","protected":false},"excerpt":{"rendered":"This as-told-to essay is based on a conversation with Robert E. Williams, a 40-year-old VC board director and&hellip;\n","protected":false},"author":3,"featured_media":357695,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[16],"tags":[155999,72240,24340,55613,64,8468,19728,607,174275,7088,12061,16776,819,242,6620,67,132,68,2452,1628],"class_list":{"0":"post-357694","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-entrepreneurship","8":"tag-advisor","9":"tag-ai-startup","10":"tag-att","11":"tag-big-company","12":"tag-business","13":"tag-customer","14":"tag-director","15":"tag-entrepreneurship","16":"tag-large-team","17":"tag-lot","18":"tag-partnership","19":"tag-risk","20":"tag-startup","21":"tag-tech","22":"tag-time","23":"tag-united-states","24":"tag-unitedstates","25":"tag-us","26":"tag-week","27":"tag-year"},"share_on_mastodon":{"url":"","error":""},"_links":{"self":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/357694","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/comments?post=357694"}],"version-history":[{"count":0,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/357694\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media\/357695"}],"wp:attachment":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media?parent=357694"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/categories?post=357694"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/tags?post=357694"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}